Nickel-Catalyzed Reductive Coupling of γ-Metalated Ketones with Unactivated Alkyl Bromides
Ning Cui, Tingzhi Lin, Yan‐En Wang, Jian Wu, Yuheng Han, Xinyang Xu, Fei Xue, Dan Xiong, Patrick J. Walsh, Jianyou Mao
Abstract
A nickel-catalyzed reductive cross-coupling reaction of aryl cyclopropyl ketones with easily accessible unactivated alkyl bromides to access aryl alkyl ketones has been developed. This strategy facilitates access to various of γ-alkyl-substituted ketones via ring opening of cyclopropyl ketones (26 examples, 50-90% yield). Initial mechanistic studies revealed that the reaction proceeds via radical cleavage of the alkyl bromide.
Topics & Concepts
AlkylChemistryArylNickelCatalysisYield (engineering)BromideCleavage (geology)Coupling reactionMedicinal chemistryOrganic chemistryGeotechnical engineeringMaterials scienceMetallurgyFracture (geology)EngineeringCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms