{"title":"Metal-free iodosulfonylation of alkynes to access (<i>E</i>)-β-iodovinyl sulfones in water.","authors":"Guiting Peng, Fang Wei, Jiang Bai, Haixin Ding, Xin Yu, Qiang Xiao","doi":"10.1039/d5ob00483g","DOIUrl":null,"url":null,"abstract":"<p><p>With the escalating concerns regarding environmental pollution caused by organic solvents, chemists are increasingly focusing on conducting organic reactions in water, nature's chosen solvent for chemical synthesis. Herein, the development of metal-free iodosulfonylation of alkynes with <i>p</i>-toluenesulfonyl cyanide and NIS for the synthesis of (<i>E</i>)-β-iodovinyl sulfones in water is reported. This reaction gives the desired products in good to excellent yields with high regio- and stereoselectivity by using water as a green solvent at room temperature. This reaction could be readily scaled up, and synthetic application was also studied.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5ob00483g","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
With the escalating concerns regarding environmental pollution caused by organic solvents, chemists are increasingly focusing on conducting organic reactions in water, nature's chosen solvent for chemical synthesis. Herein, the development of metal-free iodosulfonylation of alkynes with p-toluenesulfonyl cyanide and NIS for the synthesis of (E)-β-iodovinyl sulfones in water is reported. This reaction gives the desired products in good to excellent yields with high regio- and stereoselectivity by using water as a green solvent at room temperature. This reaction could be readily scaled up, and synthetic application was also studied.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.