{"title":"Ring-Closing Disulfenylation of Alkenoic Thioester","authors":"Kanaru Sasaki, Miari Kurihara, Hiroki Shigehisa","doi":"10.1021/acs.joc.4c02180","DOIUrl":null,"url":null,"abstract":"This study demonstrated for the first time that alkenoic thioesters can be effectively used as nucleophiles in ring-closing disulfenylation reactions. Our investigation revealed that the reaction in hexafluoroisopropanol with an electrophilic sulfur reagent significantly enhances the product yield. We gathered experimental and theoretical evidence to support the superiority of thioesters over the traditionally used benzyl sulfide. Additionally, we explored the substrate scope and identified various factors affecting the reaction selectivity and yield.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02180","RegionNum":2,"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
This study demonstrated for the first time that alkenoic thioesters can be effectively used as nucleophiles in ring-closing disulfenylation reactions. Our investigation revealed that the reaction in hexafluoroisopropanol with an electrophilic sulfur reagent significantly enhances the product yield. We gathered experimental and theoretical evidence to support the superiority of thioesters over the traditionally used benzyl sulfide. Additionally, we explored the substrate scope and identified various factors affecting the reaction selectivity and yield.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.