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Chiral Ammonium‐Capped Rhodium(0) Nanocatalysts: Synthesis, Characterization, and Advances in Asymmetric Hydrogenation in Neat Water
Author(s) -
Guyonnet Bilé Elodie,
CortelazzoPolisini Elodie,
DenicourtNowicki Audrey,
Sassine Rita,
Launay Franck,
Roucoux Alain
Publication year - 2012
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201100364
Subject(s) - rhodium , nanomaterial based catalyst , asymmetric hydrogenation , catalysis , chemistry , ammonium bromide , selectivity , enantioselective synthesis , nanoparticle , cinchonidine , counterion , bromide , organic chemistry , materials science , nanotechnology , pulmonary surfactant , biochemistry , ion
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.