{"title":"Photoredox Iron-Catalyzed Decarboxylative Radical Cyclization for the Synthesis of Oxindoles and Chroman-4-ones.","authors":"Shaoyang Han,Litao Liu,Jianqing Meng,Meichao Li,Qun Cao,Zhenlu Shen","doi":"10.1021/acs.joc.5c00669","DOIUrl":null,"url":null,"abstract":"A sustainable, photocatalytic approach for the synthesis of oxindoles and chroman-4-ones was developed using carboxylate salts as radical precursors and FeCl3 as a catalyst. The reaction proceeds via a decarboxylative radical cyclization mechanism triggered by ligand-to-metal charge transfer under visible light irradiation, operating efficiently at room temperature. This method demonstrates excellent substrate scope, including the use of various alkyl carboxylates, and functional group tolerance and offers a scalable pathway for gram-scale synthesis, highlighting its practical application.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-05-15","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://doi.org/10.1021/acs.joc.5c00669","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 sustainable, photocatalytic approach for the synthesis of oxindoles and chroman-4-ones was developed using carboxylate salts as radical precursors and FeCl3 as a catalyst. The reaction proceeds via a decarboxylative radical cyclization mechanism triggered by ligand-to-metal charge transfer under visible light irradiation, operating efficiently at room temperature. This method demonstrates excellent substrate scope, including the use of various alkyl carboxylates, and functional group tolerance and offers a scalable pathway for gram-scale synthesis, highlighting its practical application.
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.