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1. NMDA Receptors: Distribution, Role, and Insights into Neuropsychiatric Disorders

Author

Marie Beaurain, Anne-Sophie Salabert, Pierre Payoux, Emmanuel Gras, and Franck Talmont

Subjects
NMDA receptors, neuropsychiatric disorders, NMDA channel blockers, Medicine, Pharmacy and materia medica, RS1-441
Abstract

Background: N-methyl-D-aspartate receptors (NMDARs) are members of the ionotropic glutamate receptor family. These ligand-gated channels are entwined with numerous fundamental neurological functions within the central nervous system (CNS), and numerous neuropsychiatric disorders may arise from their malfunction. Methods: The purpose of the present review is to provide a detailed description of NMDARs by addressing their molecular structures, activation mechanisms, and physiological roles in the mammalian brain. In the second part, their role in various neuropsychiatric disorders including stroke, epilepsy, anti-NMDA encephalitis, Alzheimer’s and Huntington’s diseases, schizophrenia, depression, neuropathic pain, opioid-induced tolerance, and hyperalgesia will be covered. Results: Finally, through a careful exploration of the main non-competitive NMDARs antagonists (channel-blockers). Conclusion: We discuss the strengths and limitations of the various molecular structures developed for diagnostic or therapeutic purposes.

Published
2024
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2. [18F]-Radiolabelled Nanoplatforms: A Critical Review of Their Intrinsic Characteristics, Radiolabelling Methods, and Purification Techniques

Author

Maëlle Deleuziere, Éric Benoist, Isabelle Quelven, Emmanuel Gras, and Catherine Amiens

Subjects
nanoparticle, fluorine-18, radiofluorination, conjugation, characterization, purification, Organic chemistry, QD241-441
Abstract

A wide range of nano-objects is found in many applications of our everyday life. Recognition of their peculiar properties and ease of functionalization has prompted their engineering into multifunctional platforms that are supposed to afford efficient tools for the development of biomedical applications. However, bridging the gap between bench to bedside cannot be expected without a good knowledge of their behaviour in vivo, which can be obtained through non-invasive imaging techniques, such as positron emission tomography (PET). Their radiolabelling with [18F]-fluorine, a technique already well established and widely used routinely for PET imaging, with [18F]-FDG for example, and in preclinical investigation using [18F]-radiolabelled biological macromolecules, has, therefore, been developed. In this context, this review highlights the various nano-objects studied so far, the reasons behind their radiolabelling, and main in vitro and/or in vivo results obtained thereof. Then, the methods developed to introduce the radioelement are presented. Detailed indications on the chemical steps involved are provided, and the stability of the radiolabelling is discussed. Emphasis is then made on the techniques used to purify and analyse the radiolabelled nano-objects, a point that is rarely discussed despite its technical relevance and importance for accurate imaging. The pros and cons of the different methods developed are finally discussed from which future work can develop.

Published
2024
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5. N,N′-Bis(4-bromophenyl)-N,N′-dimethylurea

Author

Alexandre Pocinho, Sonia Mallet-Ladeira, Christelle Hureau, and Emmanuel Gras

Subjects
crystal structure, urea, folding, instability on storage, Crystallography, QD901-999
Abstract

The structure of the title compound, C15H14Br2N2O, at 180 K has monoclinic (P21/n) symmetry. It was obtained unexpectedly from the decomposition of the parent 4-bromo-N-tert-butoxycarbonyl-N-methyl-aniline. It exhibits an `endo' conformation with angles between the two aromatic rings slightly lower than the average values found for similar compounds on the Cambridge Structural Database. In the crystal, C—H...O hydrogen bonds and short Br...Br halogen bonds [3.444 (1) Å] are observed.

Published
2018
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7. A Robust and Efficient Production and Purification Procedure of Recombinant Alzheimers Disease Methionine-Modified Amyloid-β Peptides.

Author

Marie Hoarau, Yannick Malbert, Romain Irague, Christelle Hureau, Peter Faller, Emmanuel Gras, Isabelle André, and Magali Remaud-Siméon

Subjects
Medicine, Science
Abstract

An improved production and purification method for Alzheimer's disease related methionine-modified amyloid-β 1-40 and 1-42 peptides is proposed, taking advantage of the formation of inclusion body in Escherichia coli. A Thioflavin-S assay was set-up to evaluate inclusion body formation during growth and optimize culture conditions for amyloid-β peptides production. A simple and fast purification protocol including first the isolation of the inclusion bodies and second, two cycles of high pH denaturation/ neutralization combined with an ultrafiltration step on 30-kDa cut-off membrane was established. Special attention was paid to purity monitoring based on a rational combination of UV spectrophotometry and SDS-PAGE analyses at the various stages of the process. It revealed that this chromatography-free protocol affords good yield of high quality peptides in term of purity. The resulting peptides were fully characterized and are appropriate models for highly reproducible in vitro aggregation studies.

Published
2016
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8. Ethyl 2-[N-(tert-butylsulfinyl)carbamoyl]benzoate

Author

Aurelien Honraedt, Sonia Ladeira, Thierry Berranger, and Emmanuel Gras

Subjects
Crystallography, QD901-999
Abstract

The title compound, C14H19NO4S, was obtained in quantitative yield by Lewis acid-catalysed alcoholysis of a phtalimide precursor. An intramolecular C—H...O hydrogen bond occurs. In the crystal, centrosymmetric dimers are formed by pairs of N—H...O hydrogen bonds between the sulfinyl O atoms and the carbamoyl N—H group of a neighboring molecule. C—H...O interactions feature in the crystal structure.

Published
2011
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9. 2-Azahetaryl-2-(oxoindolin-2-ylidene)acetonitriles as Colorimetric Probes for Zn: Synthesis and Optical Properties

Author

Vladyslav V. Shcherban, Olena O. Kuleshova, Tetiana Ye. Keda, Olga V. Khilya, Emmanuel Gras, Yulian M. Volovenko, Taras Shevchenko National University of Kyiv, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
imidoylchloride, 2-azahetaryl-2-(oxoindolin-2- ylidenes)acetonitrile, [CHIM.ORGA]Chemical Sciences/Organic chemistry, General Chemical Engineering, spectrophotometry, dipyrrin-like skeleton, General Chemistry, zinc probe
Abstract

International audience; A new one-pot approach for the synthesis of the Zn2+-sensitive probes 2-azahetaryl-2-(oxoindolin-2-ylidene)acetonitriles 3a–c and 4 is described. The method includes the in situ formation of imidoylchloride and its further condensation with azahetarylacetonitrile 1. The structure of the obtained compounds is studied using 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), high-resolution mass spectrometry (HRMS), and UV–Vis spectroscopy techniques. Two model ligands both exhibiting the highest extinction coefficient and the best solubility in a Tris buffer pH 7.2/dimethyl sulfoxide (DMSO) solution, namely 5-methyl-benzothiazole derivative 3b and benzoxazole derivative 4, are thoroughly studied as colorimetric probes for Zn2+. The probe 3b has the highest sensitivity to Zn2+, showing a limit of ion detection (LOD) calculated by the 3S criterion of 0.43 μM and selectivity upon masking Cu2+ ions with Na2S2O3. The composition of the complexes in the solution was determined by the limited logarithm method. The stability constant (lg K) values of 3b-Zn of 10.27 ± 0.02 and 4-Zn of 12.5 ± 0.2 indicate the formation of complexes of average stability.

Published
2022

11. Chiral Benzothiazole Monofluoroborate Featuring Chiroptical and Oxygen-Sensitizing Properties: Synthesis and Photophysical Studies

Author

Bruno Baguenard, Stephan Guy, Olivier Maury, Frédéric Gendron, David M. Perrin, Emmanuel Gras, Amina Bensalah-Ledoux, Omar Sadek, Laura Abad Galán, Boris Le Guennic, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie - UMR5182 (LC), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Matériaux et nanostructures photoniques (MNP), Institut Lumière Matière [Villeurbanne] (ILM), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, University of British Columbia (UBC), O.S. acknowledges support from Université Toulouse III and the French-Canadian Research Fund (FCRF). B.B., S.G., A.B.-L., B.L.G., O.M., L.A.G., O.S., and E.G. acknowledge support from Agence Nationale de la Recherche (ANR-18-CE07-0016/ANR-19-CE29-0012-02). F.G. and B.L.G. acknowledge support from the European Research Council (ERC-CoG MULTIPROSMM, Grant Agreement 7255184). F.G. thanks the Région Bretagne for its support (SAD 18006-LnCPLSMM). F.G. and B.L.G. thank the French GENCI/IDRIS-CINES centers for high-performance computing resources (allocations A0020800649 and A0040800649)., ANR-18-CE07-0016,CatSAmy,CatalyseurS à base d'agrégats Amyloïdes.(2018), ANR-19-CE29-0012,SMMCPL,Luminescence polarisée circulairement de molécules-aimants à base de lanthanide(2019), European Project: 725184,H2020-EU.1.1. - EXCELLENT SCIENCE - European Research Council (ERC),MULTIPROSMM(2017), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)

Subjects
inorganic chemicals, medicine.medical_treatment, Photodynamic therapy, 010402 general chemistry, Ligands, 01 natural sciences, Stereocenter, Absorption, Physical Phenomena, chemistry.chemical_compound, medicine, Molecule, [CHIM]Chemical Sciences, Singlet state, Benzothiazoles, Boron, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Absolute configuration, Stereoisomerism, Combinatorial chemistry, Chiral resolution, 3. Good health, 0104 chemical sciences, Oxygen, Benzothiazole, chemistry, Mixtures, Enantiomer, Molecular structure
Abstract

International audience; Advances in personalized medicine are prompting the development of multimodal agents, that is, molecules that combine properties promoting various diagnostic and therapeutic applications. General approaches exploit chemical conjugation of therapeutic agents with contrast agents or the design of multimodal nanoplatforms. Herein, we report the design of a single molecule that exhibits potential for different diagnostic modes as well as the ability to sensitize oxygen, thus offering potential for photodynamic therapy. Exceptionally, this work involves the synthesis and chiral resolution of an enantiomeric pair of chiral monofluoroborates that contain a stereogenic boron atom. Combining experimental and theoretical chiroptical studies allowed the unambiguous determination of their absolute configuration. Photophysical investigations established the ability of this compound to sensitize oxygen even in the absence of heavy atoms within its structure. The synthesis of a chiral benzothiazole monofluoroborate paves a way to multimodal diagnostic tools (fluorescence and nuclear imaging) while also featuring potential therapeutic applications owing to its ability to activate oxygen to its singlet state for use in photodynamic therapy.

Published
2021

12. Phosphine-phosphonium ylides as ligands in palladium-catalysed C2-H arylation of benzoxazoles

Author

Xing Lin, Zhenyu Yao, Emmanuel Gras, Xiuling Cui, Remi Chauvin, Lianhui Wang, Engineering Research Center of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Huaqiao University, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), National Natural Science Foundation of China (Nos. 21572072 - 21602064), 111 Project (No. BC2018061, Huaqiao University (HQU), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, chemistry.chemical_element, 02 engineering and technology, General Chemistry, Benzoxazole, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Transition metal, Ylide, Yield (chemistry), [CHIM.COOR]Chemical Sciences/Coordination chemistry, Phosphonium, 0210 nano-technology, Phosphine, Palladium
Abstract

International audience; As balanced electron-rich P,C-chelating ligands, phosphine-phosphonium-ylides are considered for their ability to in situ promote palladium-catalysed direct sp2-CH arylation. Using methyl phosphonium salts of 2,2'-bis(diphenylphosphino)-1,1'-binaphtyl ("methyl-BINAPIUM") as ylide precursors under optimized reaction conditions, arylation of benzoxazole was found to proceed in moderate to high yield to give functional 2-aryl benzoxazoles. A strong anion effect of the non-salt free ylide was evidenced (TfO− > I− > PF6− ≈ salt-free). This first example of phosphonium ylides as ligands in catalytic C–H activation extends the prospect of their general implementation in homogeneous transition metal catalysis.

Published
2020

13. Straightforward convergent access to 2-arylated polysubstituted benzothiazoles

Author

Emmanuel Gras, David M. Perrin, Omar Sadek, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry [Vancouver] (UBC Chemistry), University of British Columbia (UBC), Institut des Technologies Avancées en sciences du Vivant (ITAV), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Université Toulouse III-Paul Sabatier, French Canadian Research Fund, Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, chemistry.chemical_compound, Benzothiazole, chemistry, Drug Discovery, Physical organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Reactivity (chemistry)
Abstract

International audience; A modular access to 2,4 disubstituted benzothiazoles has been achieved though the intermediacy of 4-bromo-2-iodobenzothiazole. The difference in reactivity of both halogens was advantageously exploited to achieve sequential Suzuki-Miyaura cross-coupling giving access to a range of polyaromatic derivatives featuring a central benzothiazole core.

Published
2019

14. Crystal structure of catena-poly[[[dichloridocopper(II)]-{μ-tert-butyl N-methyl-N-[4-(6-{[4-(pyridin-2-yl-κN)-1H-1,2,3-triazol-1-yl-κN 3]methyl}-1,3-benzothiazol-2-yl)phenyl]carbamato}] acetonitrile monosolvate]

Author

Christelle Hureau, Carine Duhayon, Emmanuel Gras, and Alexandre Pocinho

Subjects
Coordination sphere, Nitrile, 010405 organic chemistry, Hydrogen bond, Coordination polymer, Triazole, Stacking, General Chemistry, Crystal structure, 010402 general chemistry, Condensed Matter Physics, 01 natural sciences, Medicinal chemistry, 3. Good health, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Pyridine, General Materials Science
Abstract

In the title coordination polymer, {[CuCl2(C27H26N6O2S)]·CH3CN} n , the copper(II) ion is fivefold coordinated, with an almost perfect square-pyramidal coordination sphere. In the equatorial plane, it is ligated to a pyridine N atom and an N atom of the triazole unit and to two Cl− ions, while the apical position is occupied by the carbonyl O atom of the tert-butyl carbamate group. In the crystal, the polymer chains propagate in the [11-1] direction, with the acetonitrile solvent molecules linked to the chain by C—H...N hydrogen bonds. The chains are linked by C—H...Cl hydrogen bonds forming sheets parallel to the plane (011). The crystal packing is further consolidated by C—H...π interactions and offset π–π stacking interactions [intercentroid distance = 3.6805 (15) Å], forming a three-dimensional supramolecular structure.

Published
2018

16. Unsymmetrical diaryliodonium phenyltrifluoroborate salts: Synthesis, structure and fluorination

Author

Omar Sadek, David M. Perrin, Emmanuel Gras, Department of Chemistry [Vancouver] (UBC Chemistry), University of British Columbia (UBC), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Technologies Avancées en sciences du Vivant (ITAV), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Université Paul Sabatier, and French Canadian Research Fund

Subjects
Organotrifluoroborate, 010405 organic chemistry, Aryl, Organic Chemistry, Fluoride products, Crystal structure, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, Diaryliodonium, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Fluorination, Preliminary report, Environmental Chemistry, Reactivity (chemistry), [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Fluorinated arenes
Abstract

International audience; The unprecedented reaction of organotrifluoroborates salts of unsymmetrical diaryliodoniums to give aryl fluorides is presented. This preliminary report describes the first synthesis of unsymmetrical diaryliodonium phenyltrifluoroborates along with an exemplary x-ray crystal structure, and explores their reactivity regarding the fluorination of the diaryliodonium cation. Fluorination was found to be chemoselective, providing exclusively hindered aryl fluoride products in moderate to good yields (up to 89%).

Published
2019

17. Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes: An experimental and theoretical study

Author

Thierry Roisnel, Omar Sadek, Jean-Baptiste Sortais, Eric Clot, Christophe Darcel, Duo Wei, Vincent Dorcet, Emmanuel Gras, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut Universitaire de France (IUF), Ministère de l'Education nationale, de l’Enseignement supérieur et de la Recherche (M.E.N.E.S.R.), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Base (chemistry), 010405 organic chemistry, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, Rhenium, N methylation, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, chemistry, Reagent, Methanol, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], Physical and Theoretical Chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

The selective mono-N-methylation of anilines using methanol as an alkylating reagent was achieved with high efficiency under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands and in the presence of a base. The reaction proceeds well for a large scope of anilines (32 examples) with low loadings of both the catalyst (down to 0.5 mol%) and the base (Cs2CO3, down to 5 mol%). The mechanism of the reaction was investigated by DFT (PBE0-D3) calculations.

Published
2018

18. Expanding the Balz-Schiemann Reaction: Organotrifluoroborates Serve as Competent Sources of Fluoride Ion for Fluoro-Dediazoniation

Author

Omar Sadek, Tharwat Mohy El Dine, David M. Perrin, Emmanuel Gras, Department of Chemistry [Vancouver] (UBC Chemistry), University of British Columbia (UBC), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
chemistry.chemical_classification, Steric effects, 010405 organic chemistry, Aryl, Organic Chemistry, Salt (chemistry), chemistry.chemical_element, General Chemistry, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, Ion, chemistry.chemical_compound, chemistry, Organotrifluoroborate, Fluorine, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Balz–Schiemann reaction, Fluoride
Abstract

International audience; Abstract The Balz–Schiemann reaction endures as a method for the preparation of (hetero)aryl fluorides yet is eschewed due to the need for harsh conditions or high temperatures along with the need to isolate potentially explosive diazonium salts. In a departure from these conditions, we show that various organotrifluoroborates (RBF3−s) may serve as fluoride ion sources for solution-phase fluoro-dediazoniation in organic solvents under mild conditions. This methodology was successfully extended to a one-pot process obviating aryl diazonium salt isolation. Sterically hindered (hetero)anilines are fluorinated under unprecedentedly mild conditions in good-to-excellent yields. Taken together, this work expands the repertoire of RBF3−s to act as fluorine ion sources in an update to the classic Balz–Schiemann reaction.

Published
2018

19. N,N'-Bis(4-bromophenyl)-N,N'-dimethylurea

Author

Emmanuel Gras, Christelle Hureau, Sonia Mallet-Ladeira, Alexandre Pocinho, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)

Subjects
folding, crystal structure, instability on storage, 010405 organic chemistry, Chemistry, Hydrogen bond, Aromaticity, urea, Crystal structure, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Decomposition, 0104 chemical sciences, 3. Good health, Crystal, chemistry.chemical_compound, Halogen, lcsh:QD901-999, Urea, [CHIM.COOR]Chemical Sciences/Coordination chemistry, lcsh:Crystallography, Monoclinic crystal system
Abstract

The structure of the title compound, C15H14Br2N2O, at 180 K has monoclinic (P21/n) symmetry. It was obtained unexpectedly from the decomposition of the parent 4-bromo-N-tert-butoxycarbonyl-N-methyl-aniline. It exhibits an `endo' conformation with angles between the two aromatic rings slightly lower than the average values found for similar compounds on the Cambridge Structural Database. In the crystal, C—H...O hydrogen bonds and short Br...Br halogen bonds [3.444 (1) Å] are observed.

Published
2018

20. 300 hommes d’Aline Dalbis et Emmanuel Gras

Author

Emmanuele Coccia and Emmanuel Gras

Subjects
lcsh:Sociology (General), lcsh:HM401-1281, lcsh:H1-99, lcsh:Social sciences (General)
Abstract

Img 1 : Image tiree de 300 hommes, un film d’Aline Dalbis et Emmanuel Gras. Production : Les Films de l’Air. Img 2 : Image tiree de 300 hommes, un film d’Aline Dalbis et Emmanuel Gras. Production : Les Films de l’Air. « La nuit, je pense », par Emmanuel Gras Il est plus de deux heures du matin. La lumiere froide du plafonnier eclaire le sol carrele et le mur a la peinture verdie. Autour, l’obscurite s’etend sur les trois etages du bâtiment et ses centaines de metres de couloir. Le silence b...

Published
2017

21. Expedited route to fully substituted amino-pyrazole building blocks and their further transformations

Author

Sonia Mallet-Ladeira, Olena Kuleshova, O. V. Khilya, Viktoriya V. Dyakonenko, Yulian M. Volovenko, Emmanuel Gras, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry, Taras Shevchenko National University of Kyiv, Taras Shevchenko National University of Kyiv, Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Institute for Single Crystals, National Academy of Science (NAS) of Ukraine (SSI ), and National Academy of Sciences of Ukraine (NASU)

Subjects
Molecular complexity, Acetonitriles, 010405 organic chemistry, Chemistry, General Chemical Engineering, Regioselectivity, General Chemistry, Pyrazole, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Article, 0104 chemical sciences, lcsh:Chemistry, chemistry.chemical_compound, lcsh:QD1-999, Yield (chemistry), [CHIM.COOR]Chemical Sciences/Coordination chemistry, Derivatization
Abstract

International audience; We report here an efficient and easily reproducible two-step approach to heterocycle-substituted amino-pyrazoles from heterocyclic acetonitriles and their unprecedented subsequent transformations to fully substituted pyrazoles. Such transformations include regioselective derivatization from polyamino derivatives, formation of tetracyclic compounds in up to 45% overall yield, and deaminative transformations through diazotization, followed by arylation through Suzuki–Miyaura cross-coupling and C–H activation, providing arylated pyrazoles in up to 71% yield over four steps. This strategy allows the swift introduction of significant molecular complexity to a range of scaffolds.

Published
2017

22. The forgotten nitroaromatic phosphines as weakly donating P-ligands: An N-aryl-benzimidazolyl series in RhCl(CO) complexes

Author

Xiuling Cui, Emmanuel Gras, Carine Duhayon, Francis Lacassin, Remi Chauvin, Chongwei Zhu, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées, Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, and Huaqiao University

Subjects
Benzimidazole, Phosphines, Rhodium carbonyl complexes, 010402 general chemistry, Photochemistry, 01 natural sciences, Biochemistry, Medicinal chemistry, Coordination complex, chemistry.chemical_compound, Coordination bond, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Dichloromethane, chemistry.chemical_classification, 010405 organic chemistry, Ligand, Chemical shift, Aryl, Organic Chemistry, General Chemistry, 3. Good health, 0104 chemical sciences, P ligands, Nitroaromatic chemistry, chemistry, Nitroarylphosphines, Yield (chemistry), Nitro
Abstract

International audience; The coordination chemistry of a priori weakly σ‐donating nitroaromatic phosphines is addressed through a series of nitro‐substituted (N‐phenyl‐benzimidazol‐1‐yl)diphenylphosphines in RhI complexes. From a set of seven such phosphines L=Lxyz(′) (x, y, z=0 or 1=number of NO2 substituents at the 5, 6 and N‐Ph para positions, respectively), including the non‐nitrated parent L000 and its dicationic N‐methyl counterpart L000′, three LRhCl(COD) and seven L2RhCl(CO) complexes have been obtained in 72–95 % yield. Despite of a cis orientation of the L and CO ligands, the C=O IR stretching frequency νCO varies in the expected sense, from 1967±1 cm−1 for Lxy0 to 1978±1 cm−1 for Lxy1, and 2005 cm−1 for L000′. The 103Rh NMR chemical shift δRh varies from −288 ppm for L000 to −316±1 ppm for L10z or L01z, and −436 ppm for L000′. The νCO and δRh probes thus reveal moderate but systematic variations, and act as “orthogonal” spectroscopic indicators of the presence of nitro groups on the N‐Ph group and the benzimidazole core, respectively. For the dicationic ligand L000′, a tight electrostatic sandwiching of the Rh‐Cl bond by the benzimidazole moities is evidenced by X‐ray crystallography (RhClδ−⋅⋅⋅CN2+ ≈3.01 Å). Along with the LRhCl(CO) complexes, dinuclear side‐products (μ‐CO)(RhClL)2 were also obtained in low spectroscopic yield: for the dinitro ligand L=L011, a unique 1:6.7 clathrate structure, with dichloromethane as solvate, is also revealed by X‐ray crystallography.

Published
2017

23. Efficient Cross-Coupling of Dioxazaborocanes with α-Phosphate Enamides

Author

Nicolas Gigant, Isabelle Gillaizeau, Emmanuel Gras, and Aurélien Honraedt

Subjects
inorganic chemicals, Coupling (electronics), chemistry.chemical_compound, chemistry, Organic Chemistry, chemistry.chemical_element, Organic chemistry, Homogeneous catalysis, Physical and Theoretical Chemistry, Boron, Phosphate, Combinatorial chemistry, Palladium
Abstract

A range of readily available α-phosphate enamides were subjected to (hetero)aromatic dioxazaborocanes (DABO boronates), providing the desired α-functionalized enamides in high yields via palladium-catalyzed cross-coupling reactions. Notably, the reaction proceeds in the presence of a slight excess of boron derivatives and tolerates cyclic, nonaromatic and/or electron-rich enamides.

Published
2014

24. [18F]-Fluoride Capture and Release : azeotropic drying free nucleophilic aromatic radiofluorination assisted by a Phosphonium Borane

Author

François P. Gabbaï, Béatrice Mestre-Voegtlé, Daniel Pla, Kantapat Chansaenpak, Sébastien Schmitt, Cécile Perrio, Emmanuel Gras, Laboratoire de Développements Méthodologiques en Tomographie par Emission de Positions ( LDM-TEP ), Imagerie et Stratégies Thérapeutiques des pathologies Cérébrales et Tumorales ( ISTCT ), Université de Caen Normandie ( UNICAEN ), Normandie Université ( NU ) -Normandie Université ( NU ) -Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Centre National de la Recherche Scientifique ( CNRS ) -Université de Caen Normandie ( UNICAEN ), Normandie Université ( NU ) -Normandie Université ( NU ) -Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Centre National de la Recherche Scientifique ( CNRS ), Laboratoire de chimie de coordination ( LCC ), Centre National de la Recherche Scientifique ( CNRS ), Department of Chemistry, Texas A&M University, College Station, Texas 77843, USA., University of Texas, Laboratoire de Développements Méthodologiques en Tomographie par Emission de Positons (LDM-TEP), Service Hospitalier Frédéric Joliot (SHFJ), Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Imagerie et Stratégies Thérapeutiques des pathologies Cérébrales et Tumorales (ISTCT), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS), Service de Génétique, Centre hospitalier universitaire de Nantes (CHU Nantes), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry [Vancouver] (UBC Chemistry), University of British Columbia (UBC), Laboratoire de chimie de coordination (LCC), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Imagerie et Stratégies Thérapeutiques des pathologies Cérébrales et Tumorales (ISTCT), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Aqueous solution, 010405 organic chemistry, Elution, Radiosynthesis, Metals and Alloys, General Chemistry, Borane, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, chemistry, Nucleophile, Materials Chemistry, Ceramics and Composites, Nucleophilic substitution, Organic chemistry, [CHIM]Chemical Sciences, Phosphonium, Acetonitrile, [CHIM.RADIO]Chemical Sciences/Radiochemistry, [ CHIM.RADIO ] Chemical Sciences/Radiochemistry
Abstract

International audience; [18F]-Fluoride ready for aromatic nucleophilic substitution was prepared according to a simple process including trapping of aqueous [18F]-fluoride on a cartridge pre-loaded with the phosphonium borane [(Ph2MeP)C6H4(BMes2)]+, then releasing by elution of TBACN in dry acetonitrile. Subsequent radiofluorination was successfully applied to a model reaction and to the radiosynthesis of [18F]-setoperone.

Published
2016

25. Enantioselective synthesis of epoxides by alpha-deprotonation--electrophile trapping of achiral epoxides

Author

Emmanuel Gras, Eirene H. M. Kirton, Timothy J. Buxton, Iain D. Cameron, and David M. Hodgson

Subjects
Deprotonation, Chemistry, Organic Chemistry, Electrophile, Enantioselective synthesis, Organic chemistry, Trapping, Physical and Theoretical Chemistry, Biochemistry
Abstract

Enantioselective alpha-deprotonation of achiral epoxides 1, 21, and 26 using organolithiums in the presence of (-)-sparteine 2 and subsequent electrophile trapping gives access to enantioenriched trisubstituted epoxides 9-17, 22, 23, 27 and 28 (in up to 86% ee).

Published
2016

26. ChemInform Abstract: Metal-Free Intermolecular Azide-Alkyne Cycloaddition Promoted by Glycerol

Author

Montserrat Gómez, Marta Rodríguez-Rodríguez, Emmanuel Gras, and Miquel A. Pericàs

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, chemistry, Intermolecular force, Polymer chemistry, Alkyne, Alcohol, Reactivity (chemistry), General Medicine, Azide, HOMO/LUMO, Cycloaddition, Adduct
Abstract

Metal-free intermolecular Huisgen cycloadditions using nonactivated internal alkynes have been successfully performed in neat glycerol, both under thermal and microwave dielectric heating. In sharp contrast, no reaction occurs in other protic solvents, such as water, ethanol, or diols. DFT calculations have shown that the BnN3/glycerol adduct promotes a more important stabilization of the corresponding LUMO than that produced in the analogous BnN3/alcohol adducts, favoring the reactivity with the alkyne in the first case. The presence of copper salts in the medium did not change the reaction pathway (Cu(I) acts as spectator), except for disubstituted silylalkynes, for which desilylation takes place in contrast to the metal-free system.

Published
2016

27. A Robust and Efficient Production and Purification Procedure of Recombinant Alzheimers Disease Methionine-Modified Amyloid-beta Peptides

Author

Romain Irague, Isabelle André, Peter Faller, Yannick Malbert, Emmanuel Gras, Christelle Hureau, Magali Remaud-Simeon, Marie Hoarau, Laboratoire d'Ingénierie des Systèmes Biologiques et des Procédés (LISBP), Institut National de la Recherche Agronomique (INRA)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), APR-PRES, Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut National de la Recherche Agronomique (INRA), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
0301 basic medicine, structural-analysis, inclusion-bodies, facile method, expression, n-15, aggregation, a-beta-42, coli, [SDV]Life Sciences [q-bio], Ultrafiltration, lcsh:Medicine, medicine.disease_cause, Neutralization, Inclusion bodies, law.invention, 03 medical and health sciences, chemistry.chemical_compound, Methionine, Alzheimer Disease, law, Escherichia coli, medicine, Humans, Denaturation (biochemistry), Benzothiazoles, lcsh:Science, Polyacrylamide gel electrophoresis, Inclusion Bodies, Amyloid beta-Peptides, Multidisciplinary, Staining and Labeling, 030102 biochemistry & molecular biology, Chemistry, lcsh:R, Correction, Peptide Fragments, Recombinant Proteins, Thiazoles, 030104 developmental biology, Biochemistry, Recombinant DNA, Electrophoresis, Polyacrylamide Gel, Spectrophotometry, Ultraviolet, lcsh:Q, Thioflavin
Abstract

An improved production and purification method for Alzheimer's disease related methionine-modified amyloid-beta 1-40 and 1-42 peptides is proposed, taking advantage of the formation of inclusion body in Escherichia coli. A Thioflavin-S assay was set-up to evaluate inclusion body formation during growth and optimize culture conditions for amyloid-beta peptides production. A simple and fast purification protocol including first the isolation of the inclusion bodies and second, two cycles of high pH denaturation/neutralization combined with an ultrafiltration step on 30-kDa cut-off membrane was established. Special attention was paid to purity monitoring based on a rational combination of UV spectrophotometry and SDS-PAGE analyses at the various stages of the process. It revealed that this chromatography-free protocol affords good yield of high quality peptides in term of purity. The resulting peptides were fully characterized and are appropriate models for highly reproducible in vitro aggregation studies.

Published
2016

28. Coordination complexes and biomolecules: A wise wedding for catalysis upgrade

Author

Peter Faller, Marie Hoarau, Christelle Hureau, Emmanuel Gras, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Biomolecule, Protein design, Nanotechnology, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Catalysis, Coordination complex, Inorganic Chemistry, chemistry.chemical_compound, Bipyridine, chemistry, Materials Chemistry, Reactivity (chemistry), [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Chemoselectivity, Terpyridine
Abstract

International audience; Artificial metalloenzymes, with their high selectivity and specificity combined with a wide scope of reactivity and substrates, constitute an original approach for catalyst development. Different strategies have been proposed for their elaboration, proceeding from modification of natural enzymes using bioengineering methods to de novo protein design. Another bio-inspired methodology for the development of hybrid catalysts consists in the incorporation of coordination complexes into biomolecules, with the aim to upgrade their catalytic abilities. In these systems, the reaction performed by the naked catalyst is modulated by the well-defined structure of the host biomolecule. This conveys added value to the catalyst, such as enantioselectivity or chemoselectivity. DNA, apo-enzymes, proteins and peptides have been engaged in this approach, affording a wide diversity of reactivities and substrates. The resulting systems can then be improved by combined chemical and bioengineering optimization, allowing access to powerful catalysts. Because this approach can virtually be applied to any biomolecule or coordination complex, the elaboration of bio-based hybrid catalysts seems promising for advance in catalysis.

Published
2016

29. Cationic Boranes and Trifluoroborates: attractive alternate introduction of 18F

Author

Emmanuel GRAS, Daniel Pla, Béatrice Mestre-Voegtlé, Perrio, C., Schmitt, S., Chansaenpak, K., Fp. Gabbaï, Imagerie et Stratégies Thérapeutiques des pathologies Cérébrales et Tumorales (ISTCT), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Brunaud, Carole, and Normandie Université (NU)-Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[SDV] Life Sciences [q-bio], [SDV]Life Sciences [q-bio], [CHIM] Chemical Sciences, [CHIM.RADIO] Chemical Sciences/Radiochemistry, [CHIM]Chemical Sciences, [CHIM.RADIO]Chemical Sciences/Radiochemistry
Abstract

LDM TEP; International audience

Published
2015

30. Metal-free intermolecular azide-alkyne cycloaddition promoted by glycerol

Author

Miquel A. Pericàs, Marta Rodríguez-Rodríguez, Emmanuel Gras, Montserrat Gómez, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Institute of Chemical Research of Catalonia (ICIQ), Laboratoire de chimie de coordination (LCC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Glycerol, Azides, Free radical reactions, Alkyne, Alcohol, Photochemistry, Catalysis, Adduct, chemistry.chemical_compound, Polymer chemistry, Reactivity (chemistry), [CHIM.COOR]Chemical Sciences/Coordination chemistry, Microwaves, HOMO/LUMO, Density functionals, chemistry.chemical_classification, Cycloaddition Reaction, Organic Chemistry, Teoria del funcional de densitat, General Chemistry, Triazoles, Cycloaddition, chemistry, Metals, Alkynes, Solvents, Reaccions de radicals lliures, Azide, Copper
Abstract

International audience; Metal-free intermolecular Huisgen cycloadditions using nonactivated internal alkynes have been successfully performed in neat glycerol, both under thermal and microwave dielectric heating. In sharp contrast, no reaction occurs in other protic solvents, such as water, ethanol, or diols. DFT calculations have shown that the BnN3/glycerol adduct promotes a more important stabilization of the corresponding LUMO than that produced in the analogous BnN3/alcohol adducts, favoring the reactivity with the alkyne in the first case. The presence of copper salts in the medium did not change the reaction pathway (Cu(I) acts as spectator), except for disubstituted silylalkynes, for which desilylation takes place in contrast to the metal-free system.

Published
2015

31. Highly practical boronic acid surrogates for the Suzuki–Miyaura cross-coupling

Author

Patrice Demonchaux, Emmanuel Gras, Bruno Marchiori, Hélène Bonin, and Rodrigue Leuma-Yona

Subjects
chemistry.chemical_compound, chemistry, Aryl, Organic Chemistry, Drug Discovery, Organic chemistry, Biochemistry, Boronic acid
Abstract

Boronic acids and esters are well known substrates for the Suzuki–Miyaura cross-coupling. Yet their isolation can sometimes be tedious. We report here that the use of aryl dioxazaborocanes afford a simple isolation procedure while keeping a high efficiency in the cross-coupling process.

Published
2011

32. Fluoride Trapping and Release with Boranes: Application to 18F-Radiochemistry

Author

Emmanuel GRAS, Daniel Pla, Béatrice Mestre-Voegtlé, Schmitt, S., Perrio, C., Chansaenpak, K., Fp. Gabbaï, Imagerie et Stratégies Thérapeutiques des pathologies Cérébrales et Tumorales (ISTCT), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Normandie Université (NU)-Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS), and Brunaud, Carole

Subjects
[SDV] Life Sciences [q-bio], [SDV]Life Sciences [q-bio], [CHIM] Chemical Sciences, [CHIM.RADIO] Chemical Sciences/Radiochemistry, [CHIM]Chemical Sciences, [CHIM.RADIO]Chemical Sciences/Radiochemistry
Abstract

LDM TEP; International audience

Published
2015

33. Cationic boranes as attractive tools for radiochemistry with fluorine-18

Author

Schmitt, S., Chansaenpak, K., Gabbaï, F., Pla Queral, D., Béatrice Mestre-Voegtlé, Emmanuel GRAS, Perrio, C., Imagerie et Stratégies Thérapeutiques des pathologies Cérébrales et Tumorales (ISTCT), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Brunaud, Carole, and Normandie Université (NU)-Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM] Chemical Sciences, [CHIM.RADIO] Chemical Sciences/Radiochemistry, [CHIM]Chemical Sciences, [CHIM.RADIO]Chemical Sciences/Radiochemistry
Abstract

LDM TEP; International audience

Published
2015

34. ChemInform Abstract: Efficient Cross-Coupling of Dioxazaborocanes with α-Phosphate Enamides

Author

Emmanuel Gras, Isabelle Gillaizeau, Aurélien Honraedt, and Nicolas Gigant

Subjects
Coupling (electronics), chemistry.chemical_compound, chemistry, Computational chemistry, General Medicine, Phosphate
Abstract

Nonaromatic α-phosphate enamides react with heteroaromatic dioxazaborocanes to afford α-functionalized enamides in high yields via palladium-catalyzed cross-coupling reactions.

Published
2015

35. Naphthylaminoborane: from structural switches to frustrated Lewis pair reactivity

Author

Sarah Cadet, Daniel Pla, Emmanuel Gras, Omar Sadek, Béatrice Mestre-Voegtlé, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Centre National de la Recherche Scientifique (CNRS), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Department of Chemistry [Vancouver] (UBC Chemistry), and University of British Columbia (UBC)

Subjects
Molecular switch, Steric effects, Stereochemistry, Acenaphthene, chemistry.chemical_element, Electron, Frustrated Lewis pair, Inorganic Chemistry, Crystallography, chemistry.chemical_compound, chemistry, [CHIM]Chemical Sciences, Moiety, Molecular orbital, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Boron, ComputingMilieux_MISCELLANEOUS
Abstract

International audience; A series of naphthyl-bridged amino-borane derivatives, namely 1-(dimethylamino)-8-naphthylboranes (1, 3, 5, 7) and 5-(dimethylamino)-6-acenaphthylboranes (2, 4, 6, 8, 10, 11), differing in the steric and electronic properties of the boryl moiety, have been synthesized and fully characterized by spectroscopic and crystallographic means. Structural X-ray analysis of the peri-atom displacement and ring torsion angles served to experimentally assess the presence and magnitude of the B-N interactions. The reversible quaternarization of nitrogen has been explored and was found to provide an efficient switch corresponding to different molecular organizations. The electronic characteristics of the nature of B-N interactions were further studied by Natural Bonding Orbital analysis derived from the theoretically calculated electron densities. This real-space bonding indicator discriminates the bonding B-N contact in 5 from the nonbonding in 8, which correlates with the flexibility of the naphthyl scaffold to respond to the Lewis acidity of boron allowing shorter peri interactions. Whereas, the steric shielding imposed by the two mesityl groups, and/or the rigidity of the acenaphthene framework disrupt B-N interaction. Thus, this communication reports on the modulation of the B-N bonding continuum by means of structural tuning leading to a molecular switch, as well as its implications towards revealing FLP reactivities through the isolation of intermediates of a stepwise mechanism.

Published
2015

36. Rapport de Conjoncture du CoNRS 2014 (INC / Section 12)

Author

Chantal Andraud, Philippe Belmont, Campagne, J. M., Gaëlle Chouraqui, Emmanuel GRAS, Frédéric Lamaty, Franck Le Bideau, Jacques Lebreton, Leroux, Frédéric R., Philippe Lesot, Angela Marinetti, Christophe Meyer, Olivier Ouari, Laurent Robin, Caroline Tokarski, Laurence Vignau, Maxime Vitale, Laboratoire de Chimie - UMR5182 (LC), École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Biomolécules : Conception, Isolement, Synthèse (BioCIS), Université Paris-Sud - Paris 11 (UP11)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Centre National de la Recherche Scientifique (CNRS), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - Faculté des Sciences et des Techniques, Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie moléculaire (LCM), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), ESPCI ParisTech, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Miniaturisation pour l'Analyse, la Synthèse & la Protéomique (USR CNRS 3290), Laboratoire de l'intégration, du matériau au système (IMS), Université Sciences et Technologies - Bordeaux 1-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP), CNRS Editions, Paris, Lesot, Philippe, Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Seine-Université Paris-Seine-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Miniaturisation pour la Synthèse, l’Analyse et la Protéomique - USR 3290 (MSAP), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Lyon-Université de Lyon-École Supérieure de Chimie Physique Électronique de Lyon (CPE)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Miniaturisation pour la Synthèse, l’Analyse et la Protéomique - UAR 3290 (MSAP), Université de Lille-Centre National de la Recherche Scientifique (CNRS), Université Sciences et Technologies - Bordeaux 1 (UB)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Supérieure Chimie Physique Électronique de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, and Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Université Sciences et Technologies - Bordeaux 1

Subjects
[CHIM.ANAL] Chemical Sciences/Analytical chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, [CHIM.CATA] Chemical Sciences/Catalysis, [CHIM.COOR]Chemical Sciences/Coordination chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.COOR] Chemical Sciences/Coordination chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

National audience

Published
2014

37. Uncommon approach toward NHC-triazole complexes of palladium: Synthesis and applications

Author

Emmanuel Gras, Odile Dechy-Cabaret, Ganna Gogolieva, Jérôme Durand, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
inorganic chemicals, 010405 organic chemistry, Organic Chemistry, Triazole, chemistry.chemical_element, 010402 general chemistry, Photochemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, Adduct, Catalysis, Inorganic Chemistry, Coupling (electronics), chemistry.chemical_compound, chemistry, Materials Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Palladium
Abstract

International audience; New imidazolium-triazole adducts have been synthesized. Their coordination to palladium has been studied and the catalytic activity of the corresponding complexes has been explored in the Suzuki-Miyaura Cross Coupling.

Published
2014

38. Oxiranes and Oxirenes: Fused-ring Derivatives

Author

Hodgson, D. M., Stent, M. A. H., Reilly, M. K., Emmanuel GRAS, University of Oxford [Oxford], Key Organics Ltd., University of California [Irvine] (UCI), University of California, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Reedijk, J.

Subjects
[CHIM.COOR]Chemical Sciences/Coordination chemistry, Asymmetric desymmetrization Carbenoids Chiral C–H Insertion Dioxiranes Epoxidation Epoxides Lithiooxirane Oxiranes Oxirenes Rearrangement Reductive alkylation Ring opening
Abstract

International audience; Advances, during the period 1995–2012, in the chemistry of oxiranes (epoxides) and oxirenes fused to other ring systems are presented. Particular emphasis is placed on advances in the asymmetric synthesis of ring-fused oxiranes (metallosalen catalyzed, chiral dioxirane, or iminium salt mediated) and the reactivity of such species (ring-opening reactions, the chemistry of lithiated epoxides). The chemistry of ring-fused oxirenes remains limited.

Published
2014

39. Functionalisable N-heterocyclic carbene–triazole palladium complexes and their application in the suzuki–miyaura reaction

Author

Odile Dechy-Cabaret, Hélène Bonin, Emmanuel Gras, Ganna Gogolieva, Jérôme Durand, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées, Institut Européen des membranes (IEM), and Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)

Subjects
010405 organic chemistry, Substituent, Triazole, chemistry.chemical_element, Homogeneous catalysis, Nuclear magnetic resonance spectroscopy, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Polymer chemistry, Moiety, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Carbene, Palladium
Abstract

International audience; Seven functionalised N-heterocyclic carbene (NHC) ligands and their corresponding palladium(II) complexes have been synthesised with a triazole moiety as a modular and stable linkage between the catalytic centre and the secondary functional group. The complexes were prepared in good yields and fully characterised by NMR spectroscopy, mass spectrometry and X-ray crystallography. The complexes are active in the Suzuki–Miyaura cross-coupling reaction, with catalytic activities maintained whatever the triazolyl substituent. This opens the possibility for various functionalisations of NHC–palladium complexes.

Published
2014

40. Oxiranes and Oxirenes: Fused-ring Derivatives☆

Author

M.K. Reilly, Emmanuel Gras, Matthew A. H. Stent, and David M. Hodgson

Subjects
chemistry.chemical_compound, Dioxirane, chemistry, 010405 organic chemistry, Enantioselective synthesis, Iminium, Organic chemistry, Reactivity (chemistry), 010402 general chemistry, Ring (chemistry), 01 natural sciences, 0104 chemical sciences, Catalysis
Abstract

Advances, during the period 1995–2012, in the chemistry of oxiranes (epoxides) and oxirenes fused to other ring systems are presented. Particular emphasis is placed on advances in the asymmetric synthesis of ring-fused oxiranes (metallosalen catalyzed, chiral dioxirane, or iminium salt mediated) and the reactivity of such species (ring-opening reactions, the chemistry of lithiated epoxides). The chemistry of ring-fused oxirenes remains limited.

Published
2014

41. ChemInform Abstract: The Benzazole Scaffold: A SWAT to Combat Alzheimer′s Disease

Author

Sarah Cadet, Sabrina Noël, Emmanuel Gras, and Christelle Hureau

Subjects
Scaffold, biology, Chemistry, Spect imaging, Tau protein, biology.protein, Context (language use), General Medicine, Senile plaques, Disease, Fibril, Neuroscience, Imaging agent
Abstract

Neurodegenerative disorders including Alzheimer's disease (AD) are drawing scientists' attention within various fields, being one of the most serious diseases mankind will have to fight against in the very near future. AD is multi-factorial and is characterized by two histopathological hallmarks: the senile plaques made of amyloid-β (Aβ) peptide fibrils which also contain high levels of transition metal ions and the neurofibrillary tangles of Tau protein. Aβ aggregation, possibly modulated by metal ions, is now considered as an important factor in AD aetiology. Hence, chemists are studying the details of molecular features at the origin of the disease with special interest in Aβ aggregation and in the design of new molecules for the early diagnosis of AD or with curative properties. In this context, the benzazole molecular scaffold, included for instance in Thioflavin-T, an Aβ fibril specific dye, or the PIB imaging agent, appears to be very attractive and exhibits multiple uses. In the present review, we have thus focused our interest on the applications of benzazole derivatives for understanding, diagnosing and curing AD. After having analysed the synthetic access to 2-arylbenzazoles, we have described a selection of recent applications of such compounds aiming to combat AD. They include the use of Thioflavin-T for the monitoring of Aβ aggregation, the investigations of new PET and SPECT imaging agents for the detection of the senile plaques, the development of bi-functional molecules, encompassing the 2-arylbenzazole moiety for Aβ binding and a chelating unit for metal ions coordination for instance.

Published
2013

43. A mild entry to isoindolinones from furfural as renewable resource

Author

Emmanuel Gras, Gilles Caillot, Shridhar Hegde, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Pennakem, and Chemical services directory

Subjects
chemistry.chemical_compound, chemistry, 010405 organic chemistry, Materials Chemistry, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Chemistry, 010402 general chemistry, Furfural, 01 natural sciences, Catalysis, 0104 chemical sciences, Renewable resource
Abstract

1144-0546; A convenient transformation of furfural and derivatives into arene compounds is described. This process provides a straightforward access to isoindolinones from a renewable resource via the sequence of a tandem Ugi-Diels-Alder process followed by a ring-opening, dehydrating aromatisation. Five bonds are created and water is the sole by-product during this two-step sequence.

Published
2013

44. N-t-butanesulfinyl amide: An optimised and versatile access from readily available starting materials

Author

Gilles Caillot, Aurélien Honraedt, Emmanuel Gras, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Nucleophilic addition, 010405 organic chemistry, General Chemical Engineering, Sulfinamide, Regioselectivity, General Chemistry, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Amides, 3. Good health, 0104 chemical sciences, Chemoselectivity, chemistry.chemical_compound, chemistry, Nucleophile, Synthetic methods, Amide, Organic chemistry, Amines
Abstract

1631-0748; Abstract We report the synthesis of t-butanesulfinylphthalimide and its complete regioselective ring opening by a range of nucleophiles. Further treatment of the obtained N-t-butanesulfinyl amides under basic conditions has been shown to give t-butanesulfinamide. Although the involvement of chiral nucleophiles in this process did not allow the isolation of enantiomerically pure t-butanesulfinamide, we have accessed in a rapid and efficient fashion the original compounds bearing two H-bond sites and two chiral centers that shall potentially exhibit some organocatalytic activity by comparison with known structurally related compounds.

Published
2013

46. A new water-soluble Cu(II) chelator that retrieves Cu from Cu(amyloid-β) species, stops associated ROS production and prevents Cu(II)-induced Aβ aggregation

Author

Sonia Ladeira, Fabien Perez, Emmanuel Gras, Christelle Hureau, Bruno Alies, Stéphanie Sayen, Emmanuel Guillon, Sabrina Noël, and Jeppe T. Pedersen

Subjects
Metal ions in aqueous solution, Inorganic chemistry, Context (language use), Peptide, medicine.disease_cause, Biochemistry, Medicinal chemistry, Redox, Inorganic Chemistry, Alzheimer Disease, medicine, Chelation, Chelating Agents, chemistry.chemical_classification, Reactive oxygen species, Amyloid beta-Peptides, Ligand, Benzenesulfonates, Water, Hydrogen-Ion Concentration, Ethylenediamines, Oxygen, Oxidative Stress, chemistry, Solubility, Reactive Oxygen Species, Oxidative stress, Copper
Abstract

The synthesis of the H(2)L(2-) ligand (N,N'-Bis[(5-sulfonato-2-hydroxy)benzyl]-N,N'-dimethyl-ethane-1,2-diamine) and characterizations of the corresponding Cu(II) complex [Cu(L)(H(2)O)](2-) (1) by X-ray diffraction, EPR, UV-Visible and potentiometry are described. At pH 7.4, the affinity of Cu(II) for this ligand is approximately 4 × 10(14)M(-1). Coordination of redox active metal ions such as copper or iron to the amyloid-β (Aβ) peptide has been linked to deleterious processes encountered in the etiology of Alzheimer disease (AD), such as Aβ aggregation and reactive oxygen species (ROS) production. In this context, the ability of the H(2)L(2-) to extract Cu(II) from Cu(Aβ) species where Aβ is the peptide involved in AD, is reported as well as its capacity to redox silence the Cu(Aβ) induced ROS formation and to prevent Cu(II)-induced Aβ aggregation. Such water soluble sulfonato-derivatives of Cu(II) chelators are very interesting counterparts for in vitro study of chelators' properties required to attend further biological applications as therapeutic tools against AD.

Published
2012

47. Chiral Epoxides by Desymmetrizing Deprotonation ofmeso-Epoxides

Author

David M. Hodgson and Emmanuel Gras

Subjects
chemistry.chemical_compound, Deprotonation, chemistry, Enantioselective synthesis, Epoxide, Organic chemistry, General Medicine, General Chemistry, Catalysis, Carbanion
Abstract

Simple meso-epoxides can be asymmetrically functionalized: Ligand-assisted direct hydrogen-lithium exchange allows the generation of destabilized oxiranyl lithium species and their subsequent trapping by a wide array of electrophiles (see scheme; E = group formed by addition of electrophile). When carried out in the presence of (-)-sparteine as ligand, this reaction provides a new enantioselective route to epoxides.

Published
2002

49. ChemInform Abstract: Base Free Aryl Coupling of Diazonium Compounds and Boronic Esters: Self-Activation Allowing an Overall Highly Practical Process

Author

Dominique Delbrayelle, Emmanuel Gras, Patrice Demonchaux, and Hélène Bonin

Subjects
chemistry.chemical_classification, Coupling (electronics), chemistry.chemical_compound, Diazonium Compounds, chemistry, Aryl, Base free, General Medicine, Self activation, Combinatorial chemistry
Abstract

A series of dioxazaborocanes (III) is prepared and successfully used as starting compounds in a base-free Suzuki—Miyaura reaction with diazonium salts (IV).

Published
2010

50. ChemInform Abstract: A Formal Synthesis of (.+-.) Lycoramine via an Intramolecular Heck Reaction

Author

Catherine Guillou, Emmanuel Gras, and Claude Thal

Subjects
Formal synthesis, Stereochemistry, Chemistry, Intramolecular force, Heck reaction, General Medicine, Lycoramine
Abstract

The first use of an intramolecular Heck reaction for the construction of the quaternary centre of a galanthamine-like Amaryllidaceae alkaloid is described. The use of the acetate anion is shown as an activating factor in the 6- exo cyclisation of 5 .

Published
2010

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