{"title":"Cascade reaction of α-aryl vinyl and propargyl sulfonium salts with carbon nucleophiles: synthesis of functionalized benzyl and homoallyl thioethers†","authors":"Vilas M. Awchar , Sundarababu Baskaran","doi":"10.1039/d5ob00087d","DOIUrl":null,"url":null,"abstract":"<div><div>We report a cascade reaction of α-aryl vinyl and propargyl sulfonium salts with C-nucleophiles, resulting in the formation of functionalized benzyl and homoallyl thioethers, respectively, in good yields. In this novel reaction, a vinyl sulfonium derivative undergoes Michael addition with a C-nucleophile followed by [2,3]-sigmatropic rearrangement. This domino reaction is very general and takes place readily under mild conditions.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 11","pages":"Pages 2610-2614"},"PeriodicalIF":2.7000,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025000965","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/6 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We report a cascade reaction of α-aryl vinyl and propargyl sulfonium salts with C-nucleophiles, resulting in the formation of functionalized benzyl and homoallyl thioethers, respectively, in good yields. In this novel reaction, a vinyl sulfonium derivative undergoes Michael addition with a C-nucleophile followed by [2,3]-sigmatropic rearrangement. This domino reaction is very general and takes place readily under mild conditions.
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.
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