1, 2-Keto-Phosphoro(di)thiolation of Alkenes Enabled by Direct Photolysis of S-hydrogen Phosphoro(di)thioates

doi:10.6023/cjoc202604015

Chinese Journal of Organic Chemistry

ARTICLE

基于S-氢（二）硫代磷酸酯直接光解实现烯烃1,2-酮-(二)硫代磷酸酯化

王司渝, 黎炜^*, 蔡志华, 何林^*

石河子大学化学化工学院新疆石河子 832000

收稿日期:2026-04-08 修回日期:2026-05-10
基金资助:
新疆天山人才研究项目（编号：2023TSYCCX0122）和石河子大学高层次人才启动基金（编号：RCZK201909）资助.

1, 2-Keto-Phosphoro(di)thiolation of Alkenes Enabled by Direct Photolysis of S-hydrogen Phosphoro(di)thioates

Siyu Wang, Wei Li^*, Zhihua Cai, Lin He^*

School of Chemistry and Chemical Engineering, Xinjiang, Shihezi 832000

Received:2026-04-08 Revised:2026-05-10
Contact: ^*E-mail: liwei@gxnu.edu.cn; helin@shzu.edu.cn
Supported by:
Tianshan Talent Research Project of Xinjiang (No. 2023TSYCCX0122) and the Start-Up Fund for High-Level Talents of Shihezi University (No. RCZK201909)

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Abstract

A catalyst-free, visible-light-driven 1, 2-keto-phosphoro(di)thiolation of alkenes is reported. This method utilizes tert-butyl hydroperoxide (TBHP) and S-hydrogen phosphoro(di)thioates as difunctionalization reagents to produce β-keto phosphorothioates and β-keto phosphorodithioates in a single step. Preliminary mechanistic studies suggest that the key thiophosphoryl radicals are likely generated not via oxidation by TBHP, but through a direct photolysis of S-hydrogen phosphoro(di)thioates. Furthermore, this photochemical protocol features mild conditions and broad substrate scope while obviating the need for external metals, photocatalysts, or bases. This provides a sustainable and efficient method for the synthesis of β-keto phosphor(di)thioates.

Key words: visible-light-driven, bifunctional reaction, β-keto phosphor(di)thioates

Cite this article

Siyu Wang, Wei Li, Zhihua Cai, Lin He. 1, 2-Keto-Phosphoro(di)thiolation of Alkenes Enabled by Direct Photolysis of S-hydrogen Phosphoro(di)thioates[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604015.

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基于S-氢（二）硫代磷酸酯直接光解实现烯烃1,2-酮-(二)硫代磷酸酯化

1, 2-Keto-Phosphoro(di)thiolation of Alkenes Enabled by Direct Photolysis of S-hydrogen Phosphoro(di)thioates

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