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Sterically Controlled Cu-Catalyzed or Transition-Metal-Free Cross-Coupling of gem-Difluoroalkenes with Tertiary, Secondary, and Primary Alkyl Grignard Reagents

Wenpeng Dai, Hongyan Shi, Xianghu Zhao and Song Cao*

*Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai 200237, China, Email: scaoecust.edu.cn

W. Dai, H. Shi, X. Zhao, S. Cao, Org. Lett., 2016, 18, 4284-4287.

DOI: 10.1021/acs.orglett.6b02026 (free Supporting Information)


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Abstract

A robust copper-catalyzed or transition-metal-free alkylation of gem-difluoroalkenes with alkyl Grignard reagents proceeded very smoothly in the presence of 25 mol % of CuCN or under transition-metal-free conditions. Especially tertiary and secondary alkyl-substituted fluoroalkenes can be isolated in good to excellent yields with excellent Z stereoselectivity.

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Key Words

alkylation, vinyl fluorides


ID: J54-Y2016