Jin Wang , Yaohui Liu , Jinhai Xu , Peiyuan Li , Xiaoxi Xu , Shuo Zhang , Jie Yang , Xianxiu Xu
{"title":"Photoredox trifluoromethylation of isocyanides to access 2-trifluoromethylated quinolines and indoles†","authors":"Jin Wang , Yaohui Liu , Jinhai Xu , Peiyuan Li , Xiaoxi Xu , Shuo Zhang , Jie Yang , Xianxiu Xu","doi":"10.1039/d4qo02105c","DOIUrl":null,"url":null,"abstract":"<div><div>We herein report a divergent synthesis of 2-CF<sub>3</sub> substituted quinolines and indoles <em>via</em> photoredox radical trifluoromethylation of <em>ortho</em>-vinylphenylisocyanides. This mild and green protocol offers a broad substrate scope and good functional group tolerance. Mechanistic investigations revealed that the trifluoromethyl radical is generated through an EDA complex between Togni's reagent and a base under light irradiation.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 4","pages":"Pages 1156-1161"},"PeriodicalIF":0.0000,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924008660","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/12/13 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
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Abstract
We herein report a divergent synthesis of 2-CF3 substituted quinolines and indoles via photoredox radical trifluoromethylation of ortho-vinylphenylisocyanides. This mild and green protocol offers a broad substrate scope and good functional group tolerance. Mechanistic investigations revealed that the trifluoromethyl radical is generated through an EDA complex between Togni's reagent and a base under light irradiation.
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