Direct gem-difluoromethylenation of sp3-hybridized carbon center through copper-mediated radical/radical cross-coupling for the construction of a CH2–CF2 linkage

Haizhen Jiang; Minjun Xu; Wenjun Lu; Wenfeng Tian; Wen Wan; Yunrong Chen; Hongmei Deng; Shaoxiong Wu; Jian Hao

doi:10.1039/C5CC05677B

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Direct gem-difluoromethylenation of sp³-hybridized carbon center through copper-mediated radical/radical cross-coupling for the construction of a CH₂–CF₂ linkage†

Haizhen Jiang,*^ab Minjun Xu,^a Wenjun Lu,^a Wenfeng Tian,^a Wen Wan,^a Yunrong Chen,^a Hongmei Deng,^c Shaoxiong Wu^d and Jian Hao*^ab

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* Corresponding authors

^a Department of Chemistry, Shanghai University, Shanghai, P. R. China
E-mail: hzjiang@shu.edu.cn, jhao@shu.edu.cn

^b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China

^c Laboratory for Microstructures, Shanghai University, Shanghai, P. R. China

^d Emory NMR Research Center, Emory University, 201 Dowman Drive, Atlanta, Georgia, USA

Abstract

Efficient direct gem-difluoromethylenation of an sp³-hybridized carbon center in benzyl bromides using benzo-1,3-azolic (oxa-, thia- or aza-) difluoromethyl bromides for construction of a CH₂–CF₂ linkage has been developed through radical/radical C–C cross-coupling via two separate single electron transfer processes (SET) under the promotion of different copper sources.

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Article information

DOI: https://doi.org/10.1039/C5CC05677B
Article type: Communication
Submitted: 09 Jul 2015
Accepted: 10 Aug 2015
First published: 27 Aug 2015

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Chem. Commun., 2015,51, 15756-15759

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Direct gem-difluoromethylenation of sp³-hybridized carbon center through copper-mediated radical/radical cross-coupling for the construction of a CH₂–CF₂ linkage

H. Jiang, M. Xu, W. Lu, W. Tian, W. Wan, Y. Chen, H. Deng, S. Wu and J. Hao, Chem. Commun., 2015, 51, 15756 DOI: 10.1039/C5CC05677B

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