Haoyu Tian, Qinghe Wang, Wenyan Wei, Yan Chen, Xia Zhong, Guiwei Yao, Xun Chen, Guangkuan Zhao, Dulin Kong
{"title":"Synthesis of α-Carbonyl-α′-sulfenyl Sulfoxonium Ylides in Water at Room Temperature","authors":"Haoyu Tian, Qinghe Wang, Wenyan Wei, Yan Chen, Xia Zhong, Guiwei Yao, Xun Chen, Guangkuan Zhao, Dulin Kong","doi":"10.1021/acs.joc.4c01592","DOIUrl":null,"url":null,"abstract":"An efficient synthesis of α-carbonyl-α′-sulfenyl sulfoxonium ylides through a KIO<sub>3</sub>-promoted cross-dehydrogenative coupling reaction of aryl thiols and α-carbonyl sulfoxonium ylides in an aqueous medium at room temperature has been described. The α-carbonyl sulfoxonium ylides and aryl thiols adorned with various functional groups were well-tolerated and afforded moderate to high yields of α-carbonyl-α<i>′</i>-sulfenyl sulfoxonium ylide derivatives. Finally, by converting synthesized ylide <b>3a</b> into other valuable compounds, we demonstrated the practicality of this synthetic method.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-10-19","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.4c01592","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
An efficient synthesis of α-carbonyl-α′-sulfenyl sulfoxonium ylides through a KIO3-promoted cross-dehydrogenative coupling reaction of aryl thiols and α-carbonyl sulfoxonium ylides in an aqueous medium at room temperature has been described. The α-carbonyl sulfoxonium ylides and aryl thiols adorned with various functional groups were well-tolerated and afforded moderate to high yields of α-carbonyl-α′-sulfenyl sulfoxonium ylide derivatives. Finally, by converting synthesized ylide 3a into other valuable compounds, we demonstrated the practicality of this synthetic method.
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.