1,1-Difluoroethyl chloride (CH3CF2Cl), a novel difluoroalkylating reagent for 1,1-difluoroethylation of arylboronic acids

Jianchang Liu; Jida Zhang; Chaolin Wu; Hefu Liu; Hui Liu; Fenggang Sun; Yueyun Li; Yuying Liu; Yunhui Dong; Xinjin Li

doi:10.1039/C9RA06406K

1,1-Difluoroethyl chloride (CH₃CF₂Cl), a novel difluoroalkylating reagent for 1,1-difluoroethylation of arylboronic acids†

Jianchang Liu,^a Jida Zhang,^a Chaolin Wu,^a Hefu Liu,^a Hui Liu,

^a Fenggang Sun,^a Yueyun Li,

^a Yuying Liu,^a Yunhui Dong^a and Xinjin Li

*^ab

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* Corresponding authors

^a College of Chemistry and Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo, China
E-mail: lixj@sdut.edu.cn

^b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

Abstract

1,1-Difluoroethylated aromatics are of great importance in medicinal chemistry and related fields. 1,1-Difluoroethyl chloride (CH₃CF₂Cl), a cheap and abundant industrial raw material, is viewed as an ideal 1,1-difluoroethylating reagent, but the direct introduction of the difluoroethyl (CF₂CH₃) group onto aromatic rings using CH₃CF₂Cl has not been successfully accomplished. Herein, we disclose a nickel-catalyzed 1,1-difluoroethylation of arylboronic acids with CH₃CF₂Cl for the synthesis of (1,1-difluoroethyl)arenes.

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1,1-Difluoroethyl chloride (CH₃CF₂Cl), a novel difluoroalkylating reagent for 1,1-difluoroethylation of arylboronic acids†

Abstract

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1,1-Difluoroethyl chloride (CH₃CF₂Cl), a novel difluoroalkylating reagent for 1,1-difluoroethylation of arylboronic acids

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