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Evolutionary Catalyst Screening: Iridium‐Catalyzed Imine Hydrogenation
Author(s) -
Kluwer Alexander M.,
Detz Remko J.,
Abiri Zohar,
van der Burg Alida M.,
Reek Joost N. H.
Publication year - 2012
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.201100422
Subject(s) - catalysis , iridium , chemistry , combinatorial chemistry , imine , substrate (aquarium) , high throughput screening , organic chemistry , geology , biochemistry , oceanography
A high throughput catalyst screening is presented employing an evolutionary approach. The method comprises the optimization of initial leads by subjecting the catalysts to iterative rounds of optimization, including structural elaboration of the ligands by creating new focused libraries. Highly modular supramolecular ligands, robotized synthesis combined by high throughput experimentation creates a platform for fast catalyst development. An illustrative example for the asymmetric hydrogenation of cyclic 2,3,3‐trimethyl‐3 H ‐indole using iridium catalysts is presented. The kinetic investigation of the best catalyst yields an unusual second order in iridium, first order in hydrogen and zeroth order in substrate. Under optimized reaction conditions a TOF of 100 mol mol −1 h −1 with 96% ee could be obtained with the best catalyst. A full catalyst screening and kinetic study was conducted within a three‐week time‐frame.