Premium
NanoSelect Precious Metal Catalysts and their Use in Asymmetric Heterogeneous Catalysis
Author(s) -
Kirby Fiona,
MorenoMarrodan Carmen,
Baán Zoltan,
Bleeker Bas F.,
Barbaro Pierluigi,
Berben Peter H.,
Witte Peter T.
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402310
Subject(s) - catalysis , cinchonidine , chemistry , asymmetric hydrogenation , enantioselective synthesis , selectivity , reagent , organic chemistry , colloid , heterogeneous catalysis , combinatorial chemistry
We studied the surface modification of supported colloidal precious metal catalysts. Chiral compounds derived from cinchona alkaloids and prolinol were synthesized and used as stabilizers/reductants to yield Pd and Pt colloidal nanoparticles. The new Pd catalysts were found to be highly active and selective catalysts for the semihydrogenation of 3‐hexyn‐1‐ol to cis ‐3‐hexen‐1‐ol. The stabilizers affected the activity of the catalyst but not the selectivity. The catalysts were also evaluated in the asymmetric hydrogenation of methyl pyruvate and isophorone. No enantioselectivity was observed, which indicated that surface modification by the stabilizer did not induce chirality in the substrate. Achiral supported Pd and Pt colloidal catalysts were modified with cinchonidine. The modified Pt catalysts demonstrated a high activity for the hydrogenation of methyl pyruvate and a modest enantioselectivity of 47 %, which indicated that the chiral induction of supported colloidal catalysts is possible by modifying the catalyst surface with a chiral reagent.