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7. Insight into the Ferrier rearrangement by combining flash chemistry and superacids

Author

Bhuma N, Lebedel L, Yamashita H, Yutaka S, Zahra A, Arda A, Desire J, Michelet B, Martin-Mignot A, Abou-Hassan A, Takumi M, Marrot J, Jimenez-Barbero J, Nagaki A, Bleriot Y, and Thibaudeau S

Subjects
superacids, Ferrier, glycosyl cation, NMR
Abstract

The transformation of glycals into 2,3-unsaturated glycosyl derivatives, reported by Ferrier in 1962, is supposed toinvolve an α,β unsaturated glycosyl cation, an elusive ionic species that has still to be observed experimentally. Herein, its extended lifetime in superacidsolutions allowed its characterization by NMR-based structural analysis, supported by DFT calculations. This ionic species was further exploited in the Ferrier rearrangement to afford unsaturated nitrogen-containingC-aryl glycosides andC-alkyl glycosides under superacid and flow conditions respectively.

Published
2020

23. N-Heterocyclic Benzhydrylamines as Ligands in Palladium Complexes: Catalytic Activity in Suzuki Coupling Reaction

Author

Terrasson, Vincent, Prim, D., Marrot, J., TERRASSON, Vincent, Institut Lavoisier de Versailles (ILV), and Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

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

International audience

Published
2008

24. Crystal structure of [Co(NH3)(5)NO3](NO3)(PF6) center dot 1.5H(2)O and the vibrational bands of its normal and (NO3)-N-15-enriched cation

Author

Chacon Villalba, M.E., Navaza, A., Dupont, Nadia, Marrot, J., Varetti, E. L., Aymonino, P. J., Chimie, Structures et Propriétés de Biomatériaux et d'Agents Thérapeutiques (CSPBAT), and Université Paris 13 (UP13)-Institut Galilée-Université Sorbonne Paris Cité (USPC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Structure, Theoretical calculations, Nitrate, Infrared, Raman, Ammine cobalt complex
Abstract

1 - Article; The crystal structure of [Co(NH3)(5)NO3](NO3)(PF6) center dot 1.5 H2O was studied by X-ray diffraction methods in order to obtain the unknown molecular structure of the [Co(NH3)(5)NO3](2+) cation . The substance crystallizes in the monoclinic system, space group C2/m, with a = 18.6231(6) angstrom, b = 7.8757(3) angstrom, c = 9.6434(3) angstrom and beta = 95.484(2)degrees. An infrared and Raman study of the bromide salt was also performed and the spectra interpreted with the aid of (NO3)-N-14/(NO3)-N-15 isotopic replacement and quantum chemistry calculations.

Published
2007

25. Reversible Photoinduced Magnetic properties in the heptanuclear complex [MoIV(CN)8(CN-CuL6)]8 : a photomagnetic high-spin molecule

Author

HERRERA, J.M., MARVAUD, V., VERDAGUER, M., MARROT, J., KALISZ, M., MATHONIÈRE, Corine, Laboratoire de Chimie Inorganique et Matériaux Moléculaires (CIM2), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Université de Bordeaux (UB)

Subjects
Electron transfer, Cyanides, Photochemistry, Magnetic properties, Heterometallic complexes, [CHIM.MATE]Chemical Sciences/Material chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2004

26. N- and C-alkylation of seven-membered iminosugars generates potent glucocerebrosidase inhibitors and F508del-CFTR correctors

Author

Désiré, J., primary, Mondon, M., additional, Fontelle, N., additional, Nakagawa, S., additional, Hirokami, Y., additional, Adachi, I., additional, Iwaki, R., additional, Fleet, G. W. J., additional, Alonzi, D. S., additional, Twigg, G., additional, Butters, T. D., additional, Bertrand, J., additional, Cendret, V., additional, Becq, F., additional, Norez, C., additional, Marrot, J., additional, Kato, A., additional, and Blériot, Y., additional

Published
2014
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27. Reinvestigation of the MII(M = Ni, Co)/ TetraThiafulvaleneTetraCarboxylate system using high-throughput methods: Isolation of a molecular complex and its single-crystal-to-single-crystal transformation to a two-dimensional coordination polymer

Author

Nguyen, T.L.A., Devic, T., Mialane, P., Rivière, E., Sonnauer, A., Stock, N., Demir-Cakan, R., Morcrette, M., Livage, C., Marrot, J., Tarascon, J.M., Férey, G., Nguyen, T.L.A., Devic, T., Mialane, P., Rivière, E., Sonnauer, A., Stock, N., Demir-Cakan, R., Morcrette, M., Livage, C., Marrot, J., Tarascon, J.M., and Férey, G.

Abstract

A high-throughput methodology combined with X-ray powder diffraction measurements was used to investigate the reactivity of the TetraThiaFulvalene TetraCarboxylic acid ((TTF-TC)H4) with divalent metals (M = Ni, Co) under various reaction conditions (stoichiometry, pH, temperature). Two new crystalline phases were identified and then studied by single crystal X-ray diffraction. Whereas the first one appears to be a simple salt, the second one, formulated {[M(H2O)4]2(TTF-TC)}·4H 2O, is built of 2:1 M:TTF-TC molecular complexes and labeled MIL-136(Ni, Co) (MIL stands for Materials Institute Lavoisier). The combination of thermogravimetric analysis and thermodiffraction studies reveals that MIL-136(Ni) exhibits a complex dehydration behavior. Indeed, a partial dehydration/rehydration process led to the single-crystal-to-single-crystal transformation of the molecular compound in a two-dimensional coordination polymer formulated {[Ni2(H2O)5(TTF-TC)]} ·H2O (MIL-136′(Ni)). Magnetic and redox properties of MIL-136(Ni, Co) were investigated. Magnetic measurements indicate that all the magnetic coupling, intra-and intermolecular, are very weak; thus, the magnetic data of MIL-136(Ni, Co) have been interpreted in term of single-ion spin orbit coupling. Solid state cyclic voltammetry of MIL-136(Ni, Co) presents three reversible waves which were assigned to the redox activity of the TTF core and the metallic cations. In contrast to solids based on TTF linkers and alkaline ions, the MIL-136(Ni, Co) complexes do not act as excellent positive electrode materials for Li batteries, but present two reversible electron oxidation of the TTF core. These observations were tentatively related to the strength of the metal-carboxylate bond. © 2010 American Chemical Society.

Published
2010

28. Synthesis, structure, characterization, and redox properties of the porous MIL-68(Fe) solid

Author

Fateeva, A., Horcajada, P., Devic, T., Serre, C., Marrot, J., Grenèche, J.M., Morcrette, M., Tarascon, J.M., Maurin, G., Férey, G., Fateeva, A., Horcajada, P., Devic, T., Serre, C., Marrot, J., Grenèche, J.M., Morcrette, M., Tarascon, J.M., Maurin, G., and Férey, G.

Abstract

A new porous FeIII-based MOF, formulated Fe(OH)(BDC). (dmf) x with x ≈ 1.1 and presenting the MIL-68 topology, was prepared by reaction of an iron(III) salt and terephthalic acid (H2BDC) in N,N'-dimethylformamide (dmf) under acidic con-ditions. The structure and properties of this solid were studied by means of X-ray diffraction, thermogravimetric analysis, nitrogen sorption, 57Fe Mössbauer spectrometry, and electrochemical lithium insertion. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Published
2010

29. Functionalization in flexible porous solids: Effects on the pore opening and the host-guest interactions

Author

ESRF, Grenoble (france) - Chimie, Devic, T., Horcajada, P., Serre, C., Salles, F., Maurin, G., Moulin, B., Heurtaux, D., Clet, G., Vimont, A., Grenéche, J.-M., Le Ouay, B., Moreau, F., Magnier, E., Filinchuk, Yaroslav, Marrot, J., Lavalley, J.-C., Daturi, M., Férey, G., ESRF, Grenoble (france) - Chimie, Devic, T., Horcajada, P., Serre, C., Salles, F., Maurin, G., Moulin, B., Heurtaux, D., Clet, G., Vimont, A., Grenéche, J.-M., Le Ouay, B., Moreau, F., Magnier, E., Filinchuk, Yaroslav, Marrot, J., Lavalley, J.-C., Daturi, M., and Férey, G.

Abstract

The synthesis on the gram scale and characterization of a series of flexible functionalized iron terephthalate MIL-53(Fe) type solids are reported. Chemical groups of various polarities, hydrophilicities, and acidities (-Cl, -Br, -CF3, -CH3, -NH2, -OH, -CO2H) were introduced through the aromatic linker, to systematically modify the pore surface. X-ray powder diffraction (XRPD), molecular simulations, thermogravimetric analyses, and in situ IR and 57Fe Mössbauer spectrometries indicate some similarities with the pristine MIL-53(Fe) solid, with the adoption of the narrow pore form for all solids in both the hydrated and dry forms. Combined XRPD and computational structure determinations allow concluding that the geometry of the pore opening is predominantly correlated with the intraframework interactions rather than the steric hindrance of the substituent. Only (MIL-53(Fe)-(CF3)2) exhibits a nitrogen accessible porosity (SBET ≈ 100 m2 g-1). The adsorption of some liquids leads to pore openings showing some very specific behaviors depending on the guest-MIL-53(Fe) framework interactions, which can be related to the energy difference between the narrow and large pore forms evaluated by molecular simulation. © 2010 American Chemical Society.

Published
2010

43. Total Synthesis of the Epimer at C-6′ of the Miharamycin B Framework.

Author

Marcelo, Filipa, Abou-Jneid, Robert, Sollogoub, Matthieu, Marrot, J�r�me, Rauter, Am�lia P., and Bl�riot, Yves

Subjects
NUCLEOSIDE derivatives, ANTIBIOTICS, STEREOCHEMISTRY, GLYCOSYLATION, CRYSTALLOGRAPHY
Abstract

The total synthesis of the epimer at C-6′ of the core of the complex nucleoside antibiotic miharamycin B is reported. Opti�mization of the N-glycosylation key step involving the atypical 2-aminopurine nucleobase and a bicyclic glycosyl donor enabled to access the N9-nucleoside in reasonable yield which was further decorated. The stereochemistry at C-6′ has been secured by X-ray crystallography. [ABSTRACT FROM AUTHOR]

Published
2009
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44. Chirality Transfer in Azetidinium Ylides: An Enantioselective Route to α-Quaternary Azetidines.

Author

Drouillat, Bruno, Couty, Fran�ois, and Marrot, J�rome

Subjects
AZETIDINE, ENANTIOMERS, CHIRALITY, YLIDES, AMINO acids
Abstract

Enantiomerically pure N-allyl azetidinium ions undergo a stereoselective [2,3]-sigmatropic shift to give azetidines with an α-quaternary center. These compounds are direct precursors of �2-alkyl-2-carboxy-azetidines, a new class of constrained α-amino acids. [ABSTRACT FROM AUTHOR]

Published
2009
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45. Rearrangement of 2-Hydroxyalkylazetidines into 3-Fluoropyrrolidines.

Author

Drouillat, Bruno, Couty, Fran�ois, David, Olivier, Evano, Gwilherm, and Marrot, J�rome

Subjects
AZETIDINE, HYDROXY acids, CARBOXYLIC acids, 3-Hydroxybutyric acid, ALKYL compounds
Abstract

Upon treatment with DAST (diethylaminosulfur trifluoride) enantiopure 2-hydroxyalkylazetidines rearrange into 3-fluoropyrrolidines. The reaction is stereospecific and involves a bicyclic 1-azoniabicyclo[2.1.0]pentane intermediate which is regioselectively opened by a fluoride anion. [ABSTRACT FROM AUTHOR]

Published
2008
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46. [H4 tren]3/2·(Al6F24)·3H2O, the most condensed fluoride in the Al(OH)3-tren-HFaq.-ethanol system

Author

Adil, K., Marrot, J., Leblanc, M., and Maisonneuve, V.

Subjects
*CRYSTALS, *FLUORIDES, *HYDROGEN, *CHEMICAL bonds, *CHEMICAL structure
Abstract

Abstract: The most condensed crystalline fluoride that appears in the Al(OH)3-tren-HFaq.-ethanol system at 190°C is found to be [H4 tren]3/2·(Al6F24)·3H2O. The structure is monoclinic, P21/c, with a =21.939(1)Å, b =6.7180(2)Å, c =23.329(1)Å, β =111.324(2)°. ∞(Al6F24) chains result from the connection of (Al7F30)9− polyanions by opposite AlF6 octahedra. Hydrogen bonds are established between the ∞(Al6F24) chains and ordered or disordered [H4 tren]4+ cations and water molecules. [Copyright &y& Elsevier]

Published
2007
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49. 3-Aminopyrrolidines via Ring Rearrangement of 2-Aminomethylazetidines. Synthesis of (−)-Absouline

Author

Vargas-Sanchez, M., Couty, F., Evano, G., Prim, D., and Marrot, J.

Abstract

A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (−)-absouline was achieved on the basis of this new method.

Published
2005

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