Jin Wang , Yaohui Liu , Jinhai Xu , Peiyuan Li , Xiaoxi Xu , Shuo Zhang , Jie Yang , Xianxiu Xu
{"title":"异氰酸酯的光氧化三氟甲基化反应生成 2-三氟甲基化的喹啉和吲哚","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":"{\"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}","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}
Photoredox trifluoromethylation of isocyanides to access 2-trifluoromethylated quinolines and indoles†
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.