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Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols

Author

Listed:
  • Ziqian Bai

    (Nankai University)

  • Shiyang Zhu

    (Nankai University)

  • Yiyao Hu

    (Nankai University)

  • Peng Yang

    (Nankai University)

  • Xin Chu

    (Nankai University)

  • Gang He

    (Nankai University)

  • Hao Wang

    (Nankai University)

  • Gong Chen

    (Nankai University
    Nankai University
    Haihe Laboratory of Sustainable Chemical Transformations)

Abstract

Sulfur–heteroatom bonds such as S–S and S–N are found in a variety of natural products and often play important roles in biological processes. Despite their widespread applications, the synthesis of sulfenamides, which feature S–N bonds that may be cleaved under mild conditions, remains underdeveloped. Here, we report a method for synthesis of N-acyl sulfenamides via copper-catalyzed nitrene-mediated S-amidation reaction of thiols with dioxazolones. This method is efficient, convenient, and broadly applicable. Moreover, the resulting N-acetyl sulfenamides are highly effective S-sulfenylation reagents for the synthesis of unsymmetrical disulfides under mild conditions. The S-sulfenylation protocol enables facile access to sterically demanding disulfides that are difficult to synthesize by other means.

Suggested Citation

  • Ziqian Bai & Shiyang Zhu & Yiyao Hu & Peng Yang & Xin Chu & Gang He & Hao Wang & Gong Chen, 2022. "Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34223-7
    DOI: 10.1038/s41467-022-34223-7
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    References listed on IDEAS

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    1. Jiahui Xue & Xuefeng Jiang, 2020. "Unsymmetrical polysulfidation via designed bilateral disulfurating reagents," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    2. Xiao Xiao & Jiahui Xue & Xuefeng Jiang, 2018. "Polysulfurating reagent design for unsymmetrical polysulfide construction," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
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