{"title":"Electrocatalytic Synthesis of Dithiosulfonates From Tetrasulfides and Sodium Arylsulfinates","authors":"Xiaoxiao Li, Yingming Song, Yue Yu, Wei Wang","doi":"10.1002/ajoc.70521","DOIUrl":null,"url":null,"abstract":"<div><div>Sustainable unsymmetrical disulfide synthesis is of significant interest due to the crucial role of disulfide bonds in protein stabilization, peptide drug design, and medicinal chemistry, as exemplified by Disulfiram and ADT‐OH. Additionally, sulfone‐containing compounds such as Eletriptan and Dapsone exhibit important pharmaceutical activities. Combining these two motifs, dithiosulfonates (compounds containing a S–S–S(O)<sub>2</sub> linkage) represent a class of compounds with high research potential. Traditional methods for unsymmetrical disulfide synthesis suffer from malodorous thiols, overoxidation, toxicity, and reliance on precious metals. Although pre‐activation strategies using RSSTs reagents have enabled efficient cross‐coupling, the preparation of RSSTs themselves remains challenging, with conventional routes suffering from low atom economy and toxicity, while photocatalytic approaches require expensive iridium catalysts. Herein, we report a mild, transition‐metal‐free electrochemical approach for the synthesis of dithiosulfonates from tetrasulfides and sodium arylsulfinates. This method avoids malodorous thiols, toxic reagents, and precious metal catalysts, providing a greener and more sustainable route to structurally diverse dithiosulfonates.</div></div><div>Sustainable unsymmetrical disulfide synthesis is of significant interest due to the crucial role of disulfide bonds in protein stabilization, peptide drug design, and medicinal chemistry, as exemplified by Disulfiram and ADT‐OH. Additionally, sulfone‐containing compounds such as Eletriptan and Dapsone exhibit important pharmaceutical activities. Combining these two motifs, dithiosulfonates (compounds containing a S–S–S(O)<sub>2</sub> linkage) represent a class of compounds with high research potential. Traditional methods for unsymmetrical disulfide synthesis suffer from malodorous thiols, overoxidation, toxicity, and reliance on precious metals. Although pre‐activation strategies using RSSTs reagents have enabled efficient cross‐coupling, the preparation of RSSTs themselves remains challenging, with conventional routes suffering from low atom economy and toxicity, while photocatalytic approaches require expensive iridium catalysts. Herein, we report a mild, transition‐metal‐free electrochemical approach for the synthesis of dithiosulfonates from tetrasulfides and sodium arylsulfinates. This method avoids malodorous thiols, toxic reagents, and precious metal catalysts, providing a greener and more sustainable route to structurally diverse dithiosulfonates.</div><div>An electrochemical strategy for unsymmetrical dithiosulfonate synthesis from tetrasulfides and sodium arylsulfinates is reported, providing a mild, metal‐free approach to RSSTs reagents. This transition‐metal‐free method avoids malodorous thiols, toxic reagents, and precious metal catalysts (e.g., Ir), offering a greener route to S–S–S(O)<sub>2</sub>‐linked compounds of pharmaceutical relevance.\n<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (46KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 8","pages":"Article e70521"},"PeriodicalIF":2.3000,"publicationDate":"2026-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S219358072600231X","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2026/9/10 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Sustainable unsymmetrical disulfide synthesis is of significant interest due to the crucial role of disulfide bonds in protein stabilization, peptide drug design, and medicinal chemistry, as exemplified by Disulfiram and ADT‐OH. Additionally, sulfone‐containing compounds such as Eletriptan and Dapsone exhibit important pharmaceutical activities. Combining these two motifs, dithiosulfonates (compounds containing a S–S–S(O)2 linkage) represent a class of compounds with high research potential. Traditional methods for unsymmetrical disulfide synthesis suffer from malodorous thiols, overoxidation, toxicity, and reliance on precious metals. Although pre‐activation strategies using RSSTs reagents have enabled efficient cross‐coupling, the preparation of RSSTs themselves remains challenging, with conventional routes suffering from low atom economy and toxicity, while photocatalytic approaches require expensive iridium catalysts. Herein, we report a mild, transition‐metal‐free electrochemical approach for the synthesis of dithiosulfonates from tetrasulfides and sodium arylsulfinates. This method avoids malodorous thiols, toxic reagents, and precious metal catalysts, providing a greener and more sustainable route to structurally diverse dithiosulfonates.
Sustainable unsymmetrical disulfide synthesis is of significant interest due to the crucial role of disulfide bonds in protein stabilization, peptide drug design, and medicinal chemistry, as exemplified by Disulfiram and ADT‐OH. Additionally, sulfone‐containing compounds such as Eletriptan and Dapsone exhibit important pharmaceutical activities. Combining these two motifs, dithiosulfonates (compounds containing a S–S–S(O)2 linkage) represent a class of compounds with high research potential. Traditional methods for unsymmetrical disulfide synthesis suffer from malodorous thiols, overoxidation, toxicity, and reliance on precious metals. Although pre‐activation strategies using RSSTs reagents have enabled efficient cross‐coupling, the preparation of RSSTs themselves remains challenging, with conventional routes suffering from low atom economy and toxicity, while photocatalytic approaches require expensive iridium catalysts. Herein, we report a mild, transition‐metal‐free electrochemical approach for the synthesis of dithiosulfonates from tetrasulfides and sodium arylsulfinates. This method avoids malodorous thiols, toxic reagents, and precious metal catalysts, providing a greener and more sustainable route to structurally diverse dithiosulfonates.
An electrochemical strategy for unsymmetrical dithiosulfonate synthesis from tetrasulfides and sodium arylsulfinates is reported, providing a mild, metal‐free approach to RSSTs reagents. This transition‐metal‐free method avoids malodorous thiols, toxic reagents, and precious metal catalysts (e.g., Ir), offering a greener route to S–S–S(O)2‐linked compounds of pharmaceutical relevance.
期刊介绍：
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
