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SulfoxFluor-enabled deoxyazidation of alcohols with NaN3

Author

Listed:
  • Junkai Guo

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Xiu Wang

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Chuanfa Ni

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Xiaolong Wan

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Jinbo Hu

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

Abstract

Direct deoxyazidation of alcohols with NaN3 is a straightforward method for the synthesis of widely used alkyl azides in organic chemistry. However, known methods have some limitations such as high reaction temperatures and narrow substrate scope. Herein, a general and practical method for the preparation of alkyl azides from alcohols using NaN3 has been developed. N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor) plays an important role in this deoxyazidation process, which converts a broad range of alcohols into alkyl azides at room temperature. The power of this deoxyazidation protocol has been demonstrated by successful late-stage deoxyazidation of natural products and pharmaceutically relevant molecules.

Suggested Citation

  • Junkai Guo & Xiu Wang & Chuanfa Ni & Xiaolong Wan & Jinbo Hu, 2022. "SulfoxFluor-enabled deoxyazidation of alcohols with NaN3," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30132-x
    DOI: 10.1038/s41467-022-30132-x
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    References listed on IDEAS

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    1. Genyi Meng & Taijie Guo & Tiancheng Ma & Jiong Zhang & Yucheng Shen & Karl Barry Sharpless & Jiajia Dong, 2019. "Modular click chemistry libraries for functional screens using a diazotizing reagent," Nature, Nature, vol. 574(7776), pages 86-89, October.
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