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8 results on '"Ronan Le Goff"'

1. Insight in chitosan aerogels derivatives - Application in catalysis

Author

Ronan Le Goff, Ronan Le Coz-Botrel, Olivier Mahé, Isabelle Dez, Jean-François Brière, Sylvie Malo, Jean-Michel Goupil, Laboratoire de chimie moléculaire et thioorganique (LCMT), Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de cristallographie et sciences des matériaux (CRISMAT), École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC), Laboratoire catalyse et spectrochimie (LCS), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Université de Caen Normandie (UNICAEN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Le Havre Normandie (ULH), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Organique Fine (IRCOF), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche sur les Matériaux Avancés (IRMA), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), and Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Allylic rearrangement, Materials science, Polymers and Plastics, General Chemical Engineering, Chitosan aerogel, 02 engineering and technology, macromolecular substances, Heterogeneous catalysis, 01 natural sciences, Biochemistry, Reductive amination, Catalysis, Chitosan, chemistry.chemical_compound, Materials Chemistry, Environmental Chemistry, Substitution reaction, Textural properties, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, technology, industry, and agriculture, Aerogel, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, 021001 nanoscience & nanotechnology, 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, Chemical engineering, chemistry, 0210 nano-technology, Macromolecule
Abstract

International audience; Thanks to an aerogel formulation, an efficient heterogeneous modification of chitosan is described and offers the convenient covalent-functionalisation of primary amine of insoluble microspheres into secondary benzylic-amines with various functionalities. The SEC, XRD and textural analyses provided a better insight into the chitosan aerogels and showed that this synthetic process allows high substitution ratio (> 80%) without depressing the desirable properties of the well-defined chitosan macromolecular structure. As a proof of principle, original catalytic chitosan aerogels flanked by a phosphine-pendant were prepared and applied successfully in the heterogenous pallado-catalyzed allylic substitution reaction.

Published
2020
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2. Simulation of self-heating process on the nanoscale: A multiscale approach for molecular models of nanocomposite materials

Author

Ronan Le Goff, Greta Donati, Liberata Guadagno, Maksym Byshkin, Antonio De Nicola, Giuseppe Milano, Gianmarco Munaò, Luigi Vertuccio, Donati, G., De Nicola, A., Munao, G., Byshkin, M., Vertuccio, L., Guadagno, L., Le Goff, R., and Milano, G.

Subjects
Work (thermodynamics), Nanocomposite, Materials science, Scale (ratio), General Engineering, Bioengineering, 02 engineering and technology, General Chemistry, Carbon nanotube, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, law.invention, law, General Materials Science, Boundary value problem, 0210 nano-technology, Biological system, Joule heating, Nanoscopic scale, Voltage
Abstract

A theoretical-computational protocol to model the Joule heating process in nanocomposite materials is presented. The proposed modeling strategy is based on post processing of trajectories obtained from large scale molecular simulations. This protocol, based on molecular models, is the first one to be applied to organic nanocomposites based on carbon nanotubes (CNT). This strategy allows to keep a microscopic explicit picture of the systems, to directly catch the molecular structure underlying the process under study and, at the same time, to include macroscopic boundary conditions fixed in the experiments. As validation and first application of the proposed strategy, a detailed investigation on CNT based organic composites is reported. The effect of CNT morphologies, concentration and working conditions on Joule heating has been modelled and compared with available experiments. Further experiments are performed also in this work to increase the number of comparisons especially in specific voltage ranges where available references from literature were missing. Simulations are in both qualitative and quantitative agreement with several experiments and trends reported in the recent literature, as well as with experiments performed in this work. The proposed approach combined with large scale hybrid particle-field molecular simulations can give insights and opens to way to a rational design of self-heating nanocomposites. This journal is

Published
2020

3. Highly Stereoselective Domino Oxa-Michael/Aza-Michael/Cyclization: Synthesis of Bicyclic Lactams and Spiroox­indole Skeleton

Author

Adam Daïch, Sébastien Comesse, Ronan Le Goff, Morgane Sanselme, and Ata Martin Lawson

Subjects
Indole test, Bicyclic molecule, 010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Domino, 0104 chemical sciences, Stereocenter, Yield (chemistry), Domino process, Stereoselectivity, Physical and Theoretical Chemistry, Selectivity
Abstract

An efficient diastereoselective access to all carbon-substituted oxazolo-pyrrolidinones, including a quaternary carbon stereocenter, is described. This was achieved by using a domino process between hydroxy halogenoamides and various Michael acceptors. This strategy provided good to high yield and selectivity. Application to the diastereoselective synthesis of an enantioenriched spirooxindole skeleton in high yield and selectivity is also presented.

Published
2015
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4. Chemo-, Regio-, and Stereoselective Synthesis of Polysusbtituted Oxazolo[3,2-d][1,4]oxazepin-5(3H)ones via a Domino oxa-Michael/aza-Michael/Williamson Cycloetherification Sequence

Author

Arnaud Martel, Jordan Tasserie, Jérôme Lhoste, Abderrahman El Bouakher, Ronan Le Goff, Sébastien Comesse, Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), Normandie Université (NU)-Normandie Université (NU), Institut des Molécules et Matériaux du Mans (IMMM), and Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Steric effects, 010405 organic chemistry, Chemistry, Stereochemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Regioselectivity, Sequence (biology), Bond formation, 010402 general chemistry, 01 natural sciences, Domino, 0104 chemical sciences, Nucleophile, [CHIM]Chemical Sciences, Stereoselectivity, Domino process, ComputingMilieux_MISCELLANEOUS
Abstract

The access to new oxazolo[3,2-d][1,4]oxazepin-5(3H)-ones starting from α-bromoamido alcohols and Michael acceptors under mild conditions is presented. This domino process proved to be chemo-, regio-, and stereoselective and allows the formation of a large diversity of highly functional 7-membered rings in good yields up to 95%. The complete shift of the regioselectivity of the intermediate enolate from a C–C to a C–O bond formation, contrary to the already known alkylations of such ambident nucleophiles, is mostly triggered by steric effects. The last step of the sequence was modeled by DFT giving some important insights for this C–C vs C–O bond shift.

Published
2017
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5. Tandem aza-Michael/spiro-ring closure sequence: access to a versatile scaffold and total synthesis of (±)-coerulescine

Author

Meral Görmen, Adam Daïch, Ronan Le Goff, Ata Martin Lawson, Sébastien Comesse, Ecole Doctorale de Chimie Moléculaire PARIS CENTRE, Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL), Délégation Ifremer océan indien, Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER), Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), and Normandie Université (NU)-Normandie Université (NU)

Subjects
Tandem, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Organic Chemistry, Total synthesis, Sequence (biology), Coerulescine, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, Cascade reaction, Drug Discovery, ComputingMilieux_MISCELLANEOUS
Abstract

The total synthesis of the alkaloid (±)-coerulescine is presented. The key step of this approach is an efficient tandem aza-Michael initiated ring closure (aza-MIRC) process between ethoxymethylene-oxindole and benzyl(2-bromoethyl)carbamate. The potency of the aza-MIRC reaction was first tested onto less challenging Michael acceptors and led in good yields to the corresponding N-Cbz α-alkoxy-β-gem-disubstituted pyrrolidines. The resulting N-acyliminium precursor obtained from ethoxymethylidene-oxindole was efficiently converted in four steps, including 2 deprotections, into the targeted (±)-coerulescine.

Published
2013
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6. Carbonates: Eco-friendly Solvents for Palladium-Catalysed Direct Arylation of Heteroaromatics

Author

Jia Jia Dong, Julien Roger, Thibaut Martin, Henri Doucet, Cécile Verrier, Christophe Hoarau, Ronan Le Goff, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-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)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), Ministère de la Recherche, the CNRS, Rennes Metropole., Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and 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)

Subjects
010405 organic chemistry, Aryl, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, Benzoxazole, 010402 general chemistry, 01 natural sciences, Pollution, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Furan, Thiophene, Environmental Chemistry, Organic chemistry, Isoxazole, Thiazole, ComputingMilieux_MISCELLANEOUS, Palladium, Pyrrole
Abstract

The palladium-catalysed direct 2-, 4- or 5-arylation of a wide range of heteroaromatics with aryl halides proceed in moderate to good yields using the eco-friendly solvents carbonates. The best yields were obtained using benzoxazole or thiazole derivatives. The arylation of furan, thiophene, pyrrole, imidazole or isoxazole derivatives was found to require a more elevated reaction temperature.

Published
2010
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7. Carbonates: ecofriendly solvents for palladium-catalyzed direct 2-arylation of oxazole derivatives

Author

Cécile Verrier, Ronan Le Goff, Christophe Hoarau, Julien Roger, Henri Doucet, Institut des Sciences Chimiques de Rennes (ISCR), 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), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Ministère de la Recherche, CNRS et Rennes Metropole, 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), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Green Chemistry Technology, General Chemical Engineering, oxazoles, chemistry.chemical_element, Halide, carbonates, 010402 general chemistry, 01 natural sciences, Catalysis, chemistry.chemical_compound, Propane, Environmental Chemistry, Organic chemistry, General Materials Science, Oxazole, catalysis, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, palladium, Environmentally friendly, 0104 chemical sciences, halides, General Energy, Solvents, Carbonate, Palladium
Abstract

International audience; Bien-bon-ates. Carbonates offer an environmentally friendly alternative to standard polar solvents. Since a few years, carbonates have been employed successfully for some classical metal-catalyzed reactions. Here, the palladium-catalyzed direct 2-arylation of oxazole derivatives in carbonate solvents is reported.

Published
2009
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8. Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines

Author

Ronan Le Goff, Ata Martin Lawson, Adam Daïch, Sébastien Comesse, Pôle Européen de la Plasturgie (PEP), PEP, Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), and Normandie Université (NU)-Normandie Université (NU)

Subjects
Pyrrolidines, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Biochemistry, Martinelline, Cascade reaction, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Rapid access, [CHIM]Chemical Sciences, Organic chemistry, Pyrroles, Physical and Theoretical Chemistry, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Aniline Compounds, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Organic Chemistry, Total synthesis, Stereoisomerism, Coerulescine, [CHIM.CATA]Chemical Sciences/Catalysis, 0104 chemical sciences, Template, chemistry, Quinolines, Tricyclic
Abstract

An aza-Michael induced ring closure (aza-MIRC) tandem reaction of benzyl (2-bromoethyl)carbamate with various Michael acceptors is described. The N-Cbz-β-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (±)-coerulescine is also presented.

Published
2013
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