Hui Chen , Xuan Shang , Nan Jiang , Quan Zhou , Ke-Wen Tang , Long-Jin Zhong , Yu Liu
{"title":"光诱导铜催化烯烃的三组分烷基化,涉及硫盐的C-S键裂解","authors":"Hui Chen , Xuan Shang , Nan Jiang , Quan Zhou , Ke-Wen Tang , Long-Jin Zhong , Yu Liu","doi":"10.1039/d4qo01740d","DOIUrl":null,"url":null,"abstract":"<div><div>We report a novel visible-light-induced copper-catalyzed intermolecular 1,2-alkylarylation of alkenes with cyclic sulfonium salts and nucleophiles <em>via</em> selective C–S bond cleavage for the construction of thioether-containing 1,1-diarylalkanes. In this transformation, the remote aryl-thioether-containing aliphatic alkyl chains and nucleophiles are successively installed into the CC bond of alkenes through a radical relay coupling process in a single operation. Furthermore, the mild reaction conditions allow for good compatibility in the scope of styrenes, sulfonium salts and nucleophiles, as well as bioactive molecules and derivatives.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1498-1505"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoinduced copper-catalyzed three-component alkylarylation of alkenes involving C–S bond cleavage of sulfonium salts†\",\"authors\":\"Hui Chen , Xuan Shang , Nan Jiang , Quan Zhou , Ke-Wen Tang , Long-Jin Zhong , Yu Liu\",\"doi\":\"10.1039/d4qo01740d\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>We report a novel visible-light-induced copper-catalyzed intermolecular 1,2-alkylarylation of alkenes with cyclic sulfonium salts and nucleophiles <em>via</em> selective C–S bond cleavage for the construction of thioether-containing 1,1-diarylalkanes. In this transformation, the remote aryl-thioether-containing aliphatic alkyl chains and nucleophiles are successively installed into the CC bond of alkenes through a radical relay coupling process in a single operation. Furthermore, the mild reaction conditions allow for good compatibility in the scope of styrenes, sulfonium salts and nucleophiles, as well as bioactive molecules and derivatives.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 5\",\"pages\":\"Pages 1498-1505\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-01-08\",\"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/S2052412924008891\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"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/S2052412924008891","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Photoinduced copper-catalyzed three-component alkylarylation of alkenes involving C–S bond cleavage of sulfonium salts†
We report a novel visible-light-induced copper-catalyzed intermolecular 1,2-alkylarylation of alkenes with cyclic sulfonium salts and nucleophiles via selective C–S bond cleavage for the construction of thioether-containing 1,1-diarylalkanes. In this transformation, the remote aryl-thioether-containing aliphatic alkyl chains and nucleophiles are successively installed into the CC bond of alkenes through a radical relay coupling process in a single operation. Furthermore, the mild reaction conditions allow for good compatibility in the scope of styrenes, sulfonium salts and nucleophiles, as well as bioactive molecules and derivatives.