Synthesis of Cyclic Sulfides through Tandem Nucleophilic Substitution and Photoredox-Mediated Intramolecular Thiosulfonylation

This study presents an efficient method for synthesizing cyclic sulfides through a tandem nucleophilic substitution and a photoredox-mediated intramolecular thiosulfonylation approach. Utilizing readily available bromoalkane-tethered alkynes and potassium thiosulfonate salts, the protocol enables the construction of five-, six-, and seven-membered sulfur-containing heterocycles under mild conditions. This one-pot strategy offers a broad substrate scope, good functional group tolerance, and high yields, avoiding harsh reagents or multistep procedures. Mechanistic studies support a radical-based cyclization mechanism.

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Journal
The Journal of Organic Chemistry
Published
2026-04-21
DOI
https://doi.org/10.1021/acs.joc.6c00263
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis of Cyclic Sulfides through Tandem Nucleophilic Substitution and Photoredox-Mediated Intramolecular Thiosulfonylation

Wenchao Yang, Shanyue Li, Min-Jing Cheng, H. ZHANG et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Synthesis of Cyclic Sulfides through Tandem Nucleophilic Substitution and Photoredox-Mediated Intramolecular Thiosulfonylation

Wenchao Yang, Shanyue Li, Min-Jing Cheng, H. ZHANG, Wei Zhou, Wenjing Wang
article en

Abstract

This study presents an efficient method for synthesizing cyclic sulfides through a tandem nucleophilic substitution and a photoredox-mediated intramolecular thiosulfonylation approach. Utilizing readily available bromoalkane-tethered alkynes and potassium thiosulfonate salts, the protocol enables the construction of five-, six-, and seven-membered sulfur-containing heterocycles under mild conditions. This one-pot strategy offers a broad substrate scope, good functional group tolerance, and high yields, avoiding harsh reagents or multistep procedures. Mechanistic studies support a radical-based cyclization mechanism.

The Journal of Organic ChemistryVol. 91(17)
Shanghai Pesticide Research Institute (CN), Ministry of Education (TH), Yangzhou University (CN)
Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 20%
Sulfur-Based Synthesis Techniques
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