Yanyu Sun , Shendan Xia , Yuyan Xu , Yanmin Liu , Shuo Zhang , Zhiwei Chen
{"title":"Electrochemical-mediated cascading radical cyclization of activated alkynes: creation of 3-sulfonated coumarins and quinolinones","authors":"Yanyu Sun , Shendan Xia , Yuyan Xu , Yanmin Liu , Shuo Zhang , Zhiwei Chen","doi":"10.1080/10426507.2024.2424287","DOIUrl":null,"url":null,"abstract":"<div><div>An efficient electrochemical transformation of alkynoates into 3-sulfonated coumarins under transition metal- and oxidant-free conditions at room temperature is reported. The reaction proceeded <em>via</em> a radical-triggered domino aryl sulfonylation/5-exo cyclization/ester migration process and allowed the synthesis of 3-sulfonylated coumarins with good functional group tolerance. The reaction can be extended to the synthesis of quinolinones by capturing the sulfonyl radical with alkyne amides in good yields.</div></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 7","pages":"Pages 824-835"},"PeriodicalIF":1.4000,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650724000625","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
An efficient electrochemical transformation of alkynoates into 3-sulfonated coumarins under transition metal- and oxidant-free conditions at room temperature is reported. The reaction proceeded via a radical-triggered domino aryl sulfonylation/5-exo cyclization/ester migration process and allowed the synthesis of 3-sulfonylated coumarins with good functional group tolerance. The reaction can be extended to the synthesis of quinolinones by capturing the sulfonyl radical with alkyne amides in good yields.
期刊介绍:
Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.