Full Paper

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

  1. Elodie Guyonnet Bilé1,2,
  2. Elodie Cortelazzo-Polisini1,2,
  3. Dr. Audrey Denicourt-Nowicki1,2,*,
  4. Rita Sassine3,
  5. Prof. Franck Launay3,
  6. Prof. Alain Roucoux1,2,*

Article first published online: 17 JAN 2012

DOI: 10.1002/cssc.201100364

Issue

ChemSusChem

ChemSusChem

Special Issue: Green Nanocatalysis

Volume 5, Issue 1, pages 91–101, January 9, 2012

Additional Information

How to Cite

Guyonnet Bilé, E., Cortelazzo-Polisini, E., Denicourt-Nowicki, A., Sassine, R., Launay, F. and Roucoux, A. (2012), Chiral Ammonium-Capped Rhodium(0) Nanocatalysts: Synthesis, Characterization, and Advances in Asymmetric Hydrogenation in Neat Water. ChemSusChem, 5: 91–101. doi: 10.1002/cssc.201100364

Author Information

  1. 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. 2

    Université Européenne de Bretagne

  3. 3

    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)

*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

Publication History

  1. Issue published online: 17 JAN 2012
  2. Article first published online: 17 JAN 2012
  3. Manuscript Revised: 19 DEC 2011
  4. Manuscript Received: 13 JUL 2011

Funded by

  • Agence Nationale de la Recherche. Grant Number: ANR-08-CP2D

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article (HTML) Get PDF (1176K)

Keywords:

  • ammonium;
  • chirality;
  • hydrogenation;
  • nanoparticles;
  • surfactants

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.

View Full Article (HTML) Get PDF (1176K)