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Cobalt‐Catalyzed Asymmetric Hydrogenation of C=N Bonds Enabled by Assisted Coordination and Nonbonding Interactions
Author(s) -
Hu Yanhua,
Zhang Zhenfeng,
Zhang Jian,
Liu Yangang,
Gridnev Ilya D.,
Zhang Wanbin
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909928
Subject(s) - cobalt , catalysis , reactivity (psychology) , asymmetric hydrogenation , chemistry , ligand (biochemistry) , substrate (aquarium) , nitrogen atom , enantioselective synthesis , combinatorial chemistry , polymer chemistry , group (periodic table) , organic chemistry , pathology , geology , medicine , biochemistry , oceanography , alternative medicine , receptor
An efficient cobalt‐catalyzed asymmetric hydrogenation of C=N bonds has been realized. Chiral hydrazines were obtained in high yields and with excellent enantioselectivities (95–98 % ee). The hydrogenation went smoothly at up to 2000 substrate/catalyst and on a gram scale. The success of this reaction relies on the presence of an NHBz group in the substrates, with the reactivity and enantioselectivity improved by an assisted coordination to the cobalt atom and a nonbonding interaction with the ligand. Furthermore, this reaction has practical applications for the synthesis of several useful chiral nitrogen‐containing compounds.