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

Ziqian Bai, Shiyang Zhu, Yiyao Hu, Peng Yang, Xin Chu, Gang He, Hao Wang () and Gong Chen ()
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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

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-34223-7

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