SulfoxFluor-enabled deoxyazidation of alcohols with NaN3

  • Nat Commun. 2022 May 18;13(1):2752. doi: 10.1038/s41467-022-30132-x.
Junkai Guo  #  1 ,  Xiu Wang  #  1 ,  Chuanfa Ni  1 ,  Xiaolong Wan  1 ,  Jinbo Hu  2
Affiliations
  • 1. Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, China.
  • 2. Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, China. [email protected].
  • # Contributed equally.
PMID: 35585073 DOI: 10.1038/s41467-022-30132-x
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.

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