Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates

Yu Guo, Guotao Lin, Mengjie Zhang, Jian Xu () and Qiuling Song ()
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Yu Guo: Huaqiao University
Guotao Lin: Huaqiao University
Mengjie Zhang: Huaqiao University
Jian Xu: Huaqiao University
Qiuling Song: Huaqiao University

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract Due to the high reactivity and versatility of benzenesulfonothioates, significant advancements have been made in constructing C-S bonds. However, there are certain limitations in the synthesis of S-thiosulfonates and SS-thiosulfonates, especially when dealing with substantial steric hindrance, which poses a significant challenge. Herein, we present an innovative approach for assembling unsymmetric S-thiosulfonates and unsymmetric SS-thiosulfonates through the integration of dual copper/photoredox catalysis. Moreover, we also realized the one-pot strategy by directly using carboxylic acids as raw materials by in-situ activation of them to access S-thiosulfonates and SS-thiosulfonates without further purification and presynthesis of NHPI esters. The envisaged synthesis and utilization of these reagents are poised to pioneer an innovative pathway for fabricating a versatile spectrum of mono-, di-, and polysulfide compounds. Furthermore, they introduce a class of potent sulfenylating reagents, empowering the synthesis of intricate unsymmetrical disulfides that were previously challenging to access.

Date: 2024
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DOI: 10.1038/s41467-024-51334-5

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