镍催化的未活化烷基溴代物的 Mizoroki-Heck 型反应。
Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides.
机构信息
Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599, USA.
出版信息
Angew Chem Int Ed Engl. 2018 Dec 17;57(51):16857-16860. doi: 10.1002/anie.201810757. Epub 2018 Nov 20.
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.
摘要
本文描述了一种通用的镍催化未活化的烷基溴代物的 Mizoroki-Heck 反应。该温和的反应使用广泛的伯烷基和仲烷基溴代物高效进行，并提供了分子间交叉偶联的实例。与先前使用钯催化的碳环化反应相比，反应烯烃区域选择性显著增强。机理研究与直接碳环化一致，而不是先前观察到的钯催化下的自动串联原子转移环化和卤化物消除。
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