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New Polymer‐Supported Catalysts for the Asymmetric Transfer Hydrogenation of Acetophenone in Water – Kinetic and Mechanistic Investigations
Author(s) -
Dimroth Jonas,
Schedler Uwe,
Keilitz Juliane,
Haag Rainer,
Schomäcker Reinhard
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000955
Subject(s) - acetophenone , chemistry , transfer hydrogenation , catalysis , rhodium , enantioselective synthesis , reusability , combinatorial chemistry , asymmetric hydrogenation , organic chemistry , ruthenium , software , computer science , programming language
Abstract Heterogenization is a powerful approach for the generation of easily recyclable catalysts. In this study, a modified tethered rhodium(III)‐ p ‐toluenesulfonyl‐1,2‐diphenylethylenediamine (Rh‐TsDPEN) complex immobilized on polymeric supports was applied to kinetic and up‐scaling experiments on the asymmetric transfer hydrogenation of acetophenone in water. Study of the catalyst has helped in understanding some aspects of its operating mode. The results indicate that, in the investigated range, a simple second‐order model describes the enantioselective conversion of acetophenone to phenylethanol. Optimal reaction conditions were determined, and particularly the solution pH was found to play a decisive role for the activity and reusability of the catalyst. The good performance under optimized conditions emphasizes the practical usefulness of this recyclable catalytic system for environmentally benign asymmetric transfer hydrogenation processes.