Palladium-Catalyzed Amidation of N-Tosylhydrazones with Isocyanides

Authors

  • Fengtao Zhou,

    1. Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou (P. R. China), Fax: (+86) 20-32015266
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  • Prof. Dr. Ke Ding,

    Corresponding author
    1. Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou (P. R. China), Fax: (+86) 20-32015266
    • Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou (P. R. China), Fax: (+86) 20-32015266
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  • Prof. Dr. Qian Cai

    Corresponding author
    1. Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou (P. R. China), Fax: (+86) 20-32015266
    • Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou (P. R. China), Fax: (+86) 20-32015266
    Search for more papers by this author

Abstract

original image

Aminocarbonylation ofN-tosylhydrazones: The direct formation of ketenimines from carbenes and isocyanides is limited to the reaction of Fischer carbene complexes or some specially stabilized carbenes with isocyanides. A Pd-catalyzed amidation of N-tosylhydrazones with isocyanides via a ketenimine intermediate in the presence of water is described. The method offers a general way to synthesize amides from carbonyl compounds through one-carbon extension (see scheme).

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