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Nucleophilic Fluoromethylation of Aldehydes with Fluorobis(phenylsulfonyl)methane: The Importance of Strong Li–O Coordination and Fluorine Substitution for C[BOND]C Bond Formation

Authors

  • Xiao Shen,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Laijun Zhang,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Yanchuan Zhao,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Lingui Zhu,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Guangyu Li,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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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), Fax: (+86) 21-6416-6128
    • Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Support of our work by the National Natural Science Foundation of China (20772144, 20825209, 20832008) is gratefully acknowledged. We thank Liping Shi for her help in VT NMR experiments and Dr. Huaping Mo and Bo Chen for helpful discussions.

Abstract

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The tighter, the better! Fluorobis(phenylsulfonyl)methane reacts readily with aldehydes to give addition products in excellent yields (see scheme; LiHMDS=lithium hexamethyldisilazide), which is in sharp contrast to previous findings. Both strong Li–O coordination at low temperature and fluorine substitution play important roles in successful C[BOND]C bond formation.

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