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Cobalt‐Catalyzed Addition of Arylzinc Reagents to Alkynes to Form ortho ‐Alkenylarylzinc Species through 1,4‐Cobalt Migration
Author(s) -
Tan BoonHong,
Dong Jinghua,
Yoshikai Naohiko
Publication year - 2012
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.201204388
Subject(s) - cobalt , reagent , transmetalation , alkyne , catalysis , aryl , electrophile , chemistry , combinatorial chemistry , polymer chemistry , organic chemistry , alkyl
Migratory carbometalation : A cobalt–Xantphos complex catalyzes the addition of an arylzinc reagent to an unactivated internal alkyne; the reaction most likely involves insertion of the alkyne into an arylcobalt species and vinyl‐to‐aryl 1,4‐cobalt migration, followed by transmetalation with the arylzinc reagent. Interception of the resulting ortho ‐alkenylarylzinc species with electrophiles allows access to 1‐alkenyl arenes functionalized in the 2‐position.