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Nickel‐Catalyzed Mizoroki–Heck‐Type Reactions of Unactivated Alkyl Bromides
Author(s) -
Kwiatkowski Megan R.,
Alexanian Erik J.
Publication year - 2018
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.201810757
Subject(s) - alkyl , nickel , catalysis , chemistry , organic chemistry
The development of a general, nickel‐catalyzed alkyl‐Mizoroki–Heck reaction of unactivated alkyl bromides is described. The mild reaction proceeds efficiently using a wide range of primary and secondary alkyl bromides, and examples of intermolecular cross‐couplings are provided. Reaction alkene regioselectivity is significantly enhanced over prior carbocyclizations using palladium catalysis. Mechanistic investigations are consistent with a direct carbocyclization in contrast to the auto‐tandem atom‐transfer cyclization and halide elimination previously observed with palladium catalysis.