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A rapid access to aliphatic sulfonyl fluorides

Author

Listed:
  • Ruting Xu

    (Fuzhou University)

  • Tianxiao Xu

    (Fuzhou University)

  • Mingcheng Yang

    (Fuzhou University)

  • Tianpeng Cao

    (Fuzhou University)

  • Saihu Liao

    (Fuzhou University)

Abstract

The past few years have witnessed a fast-growing research interest on the study of sulfonyl fluorides as reactive probes in chemical biology and molecular pharmacology, which raises an urgent need for the development of effective synthetic methods to expand the toolkit. Herein, we present the invention of a facile and general approach for the synthesis of aliphatic sulfonyl fluorides via visible-light-mediated decarboxylative fluorosulfonylethylation. The method is based on abundant carboxylic acid feed stock, applicable to various alkyl carboxylic acids including primary, secondary, and tertiary acids, and is also suitable for the modification of natural products like amino acids, peptides, as well as drugs, forging a rapid, metal-free approach to build sulfonyl fluoride compound libraries of considerable structural diversity. Further diversification of the SO2F-containing products is also demonstrated, which allows for access to a range of pharmaceutically important motifs such as sultam, sulfonate, and sulfonamide.

Suggested Citation

  • Ruting Xu & Tianxiao Xu & Mingcheng Yang & Tianpeng Cao & Saihu Liao, 2019. "A rapid access to aliphatic sulfonyl fluorides," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11805-6
    DOI: 10.1038/s41467-019-11805-6
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    Cited by:

    1. Peng Wang & Honghai Zhang & Xingliang Nie & Tianxiao Xu & Saihu Liao, 2022. "Photoredox catalytic radical fluorosulfonylation of olefins enabled by a bench-stable redox-active fluorosulfonyl radical precursor," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    2. Soo Bok Kim & Dong Hyeon Kim & Han Yong Bae, 2024. "“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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