SulfoxFluor-enabled deoxyazidation of alcohols with NaN3.

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. © 2022. The Author(s).

Citation

Junkai Guo, Xiu Wang, Chuanfa Ni, Xiaolong Wan, Jinbo Hu. SulfoxFluor-enabled deoxyazidation of alcohols with NaN3. Nature communications. 2022 May 18;13(1):2752

PMID: 35585073

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