Photo-induced carboxylation of C(sp2)−S bonds in aryl thiols and derivatives with CO2

Jie Liu, Wei Wang, Li-Li Liao, Wei Zhang, Jun-Ping Yue, Yi Liu, Xiao-Wang Chen, Jian-Heng Ye () and Da-Gang Yu ()
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Jie Liu: Sichuan University
Wei Wang: Sichuan University
Li-Li Liao: Sichuan University
Wei Zhang: Sichuan University
Jun-Ping Yue: Sichuan University
Yi Liu: Sichuan University
Xiao-Wang Chen: Sichuan University
Jian-Heng Ye: Sichuan University
Da-Gang Yu: Sichuan University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Aryl thiols have proven to be a useful class of electron donors and hydrogen atom sources in photochemical processes. However, the direct activation and functionalization of C(sp2)–S bonds in aryl thiols remains elusive in the field of photochemistry. Herein, a photochemical carboxylation of C(sp2)–S bonds in aryl thiols with CO2 is reported, providing a synthetic route to important aryl carboxylic acids. Moreover, different kinds of aryl thiol derivatives, benzeneselenol and diphenyl diselenide also show moderate-to-high reactivity in this transformation. Mechanistic studies, including DFT calculations, suggest that the in situ generated carbon dioxide radical anion (CO2•−) and disulfide might be the key intermediates, which undergo radical substitution to yield products. This reaction features mild and catalyst-free conditions, good functional group tolerance and wide substrate scope. Furthermore, the efficient degradation of polyphenylene sulfide highlights the usefulness of this methodology.

Date: 2024
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DOI: 10.1038/s41467-024-53351-w

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