Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides.

ABSTRACT: 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.

SUBMITTER: Kwiatkowski MR 

PROVIDER: S-EPMC6328373 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature