Accessing 3-Sulfonated Vinylsilanes via Sulfonylation of α-Bromoallylsilane Involving Photoinduced Radical Sulfur Dioxide Insertion

A photocatalytic strategy for synthesizing 3-sulfonated vinylsilanes through photoinduced radical sulfur dioxide insertion into α-bromoallylsilane is presented. Using aryldiazonium or thianthrenium salts as aryl radical precursors, the reaction operates under mild conditions with various photocatalysts and SO<sub>2</sub> sources. It exhibits a broad substrate scope, especially offering a practical approach for late-stage modification of drug molecules by providing valuable sulfone-containing vinylsilanes.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-08-04
DOI
https://doi.org/10.1021/acs.joc.5c01237
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Accessing 3-Sulfonated Vinylsilanes via Sulfonylation of α-Bromoallylsilane Involving Photoinduced Radical Sulfur Dioxide Insertion

Luo Yang, Shuo Gao, Jie Wang, Xiaoqing Li et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Accessing 3-Sulfonated Vinylsilanes via Sulfonylation of α-Bromoallylsilane Involving Photoinduced Radical Sulfur Dioxide Insertion

Luo Yang, Shuo Gao, Jie Wang, Xiaoqing Li, Xiangsheng Xu
article en

Abstract

A photocatalytic strategy for synthesizing 3-sulfonated vinylsilanes through photoinduced radical sulfur dioxide insertion into α-bromoallylsilane is presented. Using aryldiazonium or thianthrenium salts as aryl radical precursors, the reaction operates under mild conditions with various photocatalysts and SO<sub>2</sub> sources. It exhibits a broad substrate scope, especially offering a practical approach for late-stage modification of drug molecules by providing valuable sulfone-containing vinylsilanes.

The Journal of Organic ChemistryVol. 90(32)
Zhejiang University of Technology (CN)
Clean water and sanitation
Openalex Percentile: Top 86%
Sulfur-Based Synthesis Techniques
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