Chiral Ammonium-Capped Rhodium(0) Nanocatalysts: Synthesis, Characterization, and Advances in Asymmetric Hydrogenation in Neat Water - Sorbonne Université Access content directly
Journal Articles ChemSusChem Year : 2012

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

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.

Domains

Catalysis

Dates and versions

hal-00750000 , version 1 (08-11-2012)

Identifiers

Cite

Elodie Guyonnet Bil É, Elodie Cortelazzo-Polisini, Audrey Denicourt-Nowicki, Rita Sassine, Franck Launay, et al.. Chiral Ammonium-Capped Rhodium(0) Nanocatalysts: Synthesis, Characterization, and Advances in Asymmetric Hydrogenation in Neat Water. ChemSusChem, 2012, 5, pp.91-101. ⟨10.1002/cssc.201100364⟩. ⟨hal-00750000⟩
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