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Nickel‐Catalyzed Asymmetric Hydrogenation of Hydrazones
Author(s) -
Li Bowen,
Liu Dan,
Hu Yanhua,
Chen Jianzhong,
Zhang Zhenfeng,
Zhang Wanbin
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100642
Subject(s) - chemistry , catalysis , hydrazone , nickel , imine , enamine , tautomer , dissociation (chemistry) , asymmetric hydrogenation , yield (engineering) , organic chemistry , catalytic cycle , enantioselective synthesis , materials science , metallurgy
An efficient nickel‐catalyzed asymmetric hydrogenation of hydrazones to chiral hydrazines has been realized with up to 99 % yield and 99.4 : 0.6 er. Deuterium labelling experiments indicated that the hydrazone substrates undergo imine‐enamine tautomerization in the mixed solvents. Studies on the effects of acids revealed that the required acid assistance promoted the dissociation of the active nickel catalyst in the catalytic cycle.