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Chiral Ammonium-Capped Rhodium(0) Nanocatalysts: Synthesis, Characterization, and Advances in Asymmetric Hydrogenation in Neat Water

Authors

  • Elodie Guyonnet Bilé,

    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35 708 Rennes Cedex 7 (France), Fax: (+33) (0)2 23 23 81 99
    2. Université Européenne de Bretagne
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  • Elodie Cortelazzo-Polisini,

    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35 708 Rennes Cedex 7 (France), Fax: (+33) (0)2 23 23 81 99
    2. Université Européenne de Bretagne
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  • Dr. Audrey Denicourt-Nowicki,

    Corresponding author
    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35 708 Rennes Cedex 7 (France), Fax: (+33) (0)2 23 23 81 99
    2. Université Européenne de Bretagne
    • Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35 708 Rennes Cedex 7 (France), Fax: (+33) (0)2 23 23 81 99
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  • Rita Sassine,

    1. Laboratoire de Réactivité de Surface, UMR CNRS 7197, Equipe “Etude de Supports Poreux Activés et Catalyse pour l'Environnement“, UPMC - site Le Raphaël, Bât. A/B 1er étage Pièce 1B05, case courrier 178, 3 rue Galilée, 94200 Ivry-sur-Seine (France)
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  • Prof. Franck Launay,

    1. Laboratoire de Réactivité de Surface, UMR CNRS 7197, Equipe “Etude de Supports Poreux Activés et Catalyse pour l'Environnement“, UPMC - site Le Raphaël, Bât. A/B 1er étage Pièce 1B05, case courrier 178, 3 rue Galilée, 94200 Ivry-sur-Seine (France)
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  • Prof. Alain Roucoux

    Corresponding author
    1. Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35 708 Rennes Cedex 7 (France), Fax: (+33) (0)2 23 23 81 99
    2. Université Européenne de Bretagne
    • Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35 708 Rennes Cedex 7 (France), Fax: (+33) (0)2 23 23 81 99
    Search for more papers by this author

Abstract

Optically active amphiphilic compounds derived from N-methylephedrine, N-methylprolinol, or cinchona derivatives possessing bromide or chiral lactate counterions were efficiently used as protective agents for rhodium(0) nanoparticles. The full characterization of these surfactants and the obtained nanocatalysts was performed by means of different techniques. These spherical nanoparticles, with sizes between 0.8–2.5 nm depending on the stabilizer, were evaluated in the hydrogenation of model substrates in neat water as a green solvent. The rhodium catalysts showed relevant kinetic properties, but modest enantiomeric excess values of up to 13 % in the hydrogenation of ethyl pyruvate. They were also investigated in the hydrogenation of disubstituted arenes, such as m-methylanisole, providing interesting catalytic activities and a preferential cis selectivity of around 80 %; however, no asymmetric induction was observed.

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