Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles
Author(s) -
Alan H. Cherney,
Sarah E. Reisman
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja508067c
Subject(s) - chemistry , allylic rearrangement , stereocenter , regioselectivity , electrophile , aryl , catalysis , reagent , combinatorial chemistry , substrate (aquarium) , nickel , organic chemistry , enantioselective synthesis , alkyl , oceanography , geology
A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.
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