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Copper-Catalyzed Difluoromethylation of β,γ-Unsaturated Carboxylic Acids: An Efficient Allylic Difluoromethylation

Authors

  • Dr. Zhengbiao He,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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  • Mingyou Hu,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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  • Tao Luo,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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  • Lingchun Li,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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  • Prof. Dr. Jinbo Hu

    Corresponding author
    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
    • Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China)
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  • Support of our work by the National Basic Research Program of China (2012CB215500 and 2012CB821600) and the National Natural Science Foundation of China (20825209, 20832008) is gratefully acknowledged. Professor Kuo-Wei Huang is thanked for helpful discussions.

Abstract

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Not one but two! A new strategy for the regiospecific construction of compounds with allylic CF2H groups has been developed. The decarboxylative (phenylsulfonyl)difluoromethylation of β,γ-unsaturated carboxylic acids is catalyzed by a Lewis acid (CuCl2⋅2 H2O), and the resulting product easily undergoes desulfonylation.

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