{"title":"芳草硫酸催化的Caryl−F键活化：氧化吲哚的合成","authors":"Shengyun Liu , Mingying Li , Wei Xiao , Jie Wu","doi":"10.1039/d4qo01888e","DOIUrl":null,"url":null,"abstract":"<div><div>Single-electron reduction of the C<sub>aryl</sub>–F bond is quite challenging due to its high reduction potential. Herein, we report an arenethiolate-catalyzed single-electron reduction of the C<sub>aryl</sub>–F bond to access oxindoles. A variety of oxindoles are provided in moderate to excellent yields through a single-electron reduction/cyclization/single-electron oxidation process. Furthermore, the 1,5-HAT of inert C–H could be achieved with this method. A plausible pathway with arenethiolate as a SET catalyst is proposed on the basis of mechanistic studies.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 7","pages":"Pages 2314-2320"},"PeriodicalIF":0.0000,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Arenethiolate-catalyzed Caryl–F bond activation: synthesis of oxindoles†\",\"authors\":\"Shengyun Liu , Mingying Li , Wei Xiao , Jie Wu\",\"doi\":\"10.1039/d4qo01888e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Single-electron reduction of the C<sub>aryl</sub>–F bond is quite challenging due to its high reduction potential. Herein, we report an arenethiolate-catalyzed single-electron reduction of the C<sub>aryl</sub>–F bond to access oxindoles. A variety of oxindoles are provided in moderate to excellent yields through a single-electron reduction/cyclization/single-electron oxidation process. Furthermore, the 1,5-HAT of inert C–H could be achieved with this method. A plausible pathway with arenethiolate as a SET catalyst is proposed on the basis of mechanistic studies.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 7\",\"pages\":\"Pages 2314-2320\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-02-12\",\"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/S2052412924009057\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/12/30 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/S2052412924009057","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/12/30 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Arenethiolate-catalyzed Caryl–F bond activation: synthesis of oxindoles†
Single-electron reduction of the Caryl–F bond is quite challenging due to its high reduction potential. Herein, we report an arenethiolate-catalyzed single-electron reduction of the Caryl–F bond to access oxindoles. A variety of oxindoles are provided in moderate to excellent yields through a single-electron reduction/cyclization/single-electron oxidation process. Furthermore, the 1,5-HAT of inert C–H could be achieved with this method. A plausible pathway with arenethiolate as a SET catalyst is proposed on the basis of mechanistic studies.
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