Photocatalytic Synthesis of 1,2-Sulfinate-Sulfonate Esters by Four-Component Radical-Polar Crossover Cyclization

Structurally diverse 1,2-sulfinate-sulfonate esters are shown to be conveniently prepared through visible light-induced sulfonation and sulfinylation of difunctionalized alkenes using alcohols and NaHSO<sub>3</sub>. The reactions proceed under mild conditions in the presence of photocatalysts and HCO<sub>2</sub>H as an additive, exhibiting good functional group tolerance and a broad scope. Furthermore, this method is scalable and has been successfully applied to synthesize 1,2-disulfonic acid esters. A plausible mechanistic pathway has been proposed based on control experiments.

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Publication Details

Journal
Organic Letters
Published
2025-09-04
DOI
https://doi.org/10.1021/acs.orglett.5c03152
Citations
3
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.81

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article

Photocatalytic Synthesis of 1,2-Sulfinate-Sulfonate Esters by Four-Component Radical-Polar Crossover Cyclization

Ligang Huang, Xu Zhou, Hui Xu, Chao Shu et al.
3 citations
Organic Letters
Sulfur-Based Synthesis Techniques
2.81
article

Photocatalytic Synthesis of 1,2-Sulfinate-Sulfonate Esters by Four-Component Radical-Polar Crossover Cyclization

Ligang Huang, Xu Zhou, Hui Xu, Chao Shu, Yongxin Zhang, Xing Fang
article en
3 citations

Abstract

Structurally diverse 1,2-sulfinate-sulfonate esters are shown to be conveniently prepared through visible light-induced sulfonation and sulfinylation of difunctionalized alkenes using alcohols and NaHSO<sub>3</sub>. The reactions proceed under mild conditions in the presence of photocatalysts and HCO<sub>2</sub>H as an additive, exhibiting good functional group tolerance and a broad scope. Furthermore, this method is scalable and has been successfully applied to synthesize 1,2-disulfonic acid esters. A plausible mechanistic pathway has been proposed based on control experiments.

Organic LettersVol. 27(37)
Central China Normal University (CN), Ministry of Education (ME), Wuhan Institute of Technology (CN)
National Natural Science Foundation of China, Central China Normal University, Department of Science and Technology, Hubei Provincial People's Government, National Key Research and Development Program of China
Openalex Percentile: Top 9%
Sulfur-Based Synthesis Techniques
2.81
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