{"title":"Photocatalytic Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles","authors":"Fei Chen*, Jun-Ya Guo, Yun-Hong Jia, Jingze Li, Yi-Jie Zhu, Yu-Xin Lai, Yi-Nan Zhang, Si-Yu Tian, Shu-Man Wang, Yang Zheng* and Yunhe Lv, ","doi":"10.1021/acs.joc.4c0317410.1021/acs.joc.4c03174","DOIUrl":null,"url":null,"abstract":"<p >A photocatalytic radical sulfonarylation of <i>N</i>-arylacrylamides via a three-component cascade cyclopropyl alcohol ring opening/sulfur dioxide insertion/sulfonyl radical addition/cyclization sequence has been developed. This method employs cyclopropyl alcohols as the precursors of β-carbonyl alkyl radicals and Na<sub>2</sub>S<sub>2</sub>O<sub>5</sub> as a cheap source of sulfur dioxide. By using this cascade procedure, a wide variety of γ-keto-sulfone-substituted oxindoles were facilely synthesized.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 12","pages":"4261–4270 4261–4270"},"PeriodicalIF":3.6000,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c03174","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
A photocatalytic radical sulfonarylation of N-arylacrylamides via a three-component cascade cyclopropyl alcohol ring opening/sulfur dioxide insertion/sulfonyl radical addition/cyclization sequence has been developed. This method employs cyclopropyl alcohols as the precursors of β-carbonyl alkyl radicals and Na2S2O5 as a cheap source of sulfur dioxide. By using this cascade procedure, a wide variety of γ-keto-sulfone-substituted oxindoles were facilely synthesized.
期刊介绍:
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.