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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

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

Kwiatkowski Megan R MR Alexanian Erik J EJ

Angewandte Chemie (International ed. in English) 20181120 51

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 a ...[more]

PMID: 30358060

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