Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides
Megan R Kwiatkowski1, Erik J Alexanian1
1Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599, USA.
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.
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