Yu-Zhao Wang , Di-Di Tang , Han-Yue Zhang , Xiao-Yue Ma , De-Hua Xing , Chenjiang Liu , Yu Xia , Yan Li
{"title":"可见光诱导烯烃的三组分自由基级联1,2-二烷基化反应","authors":"Yu-Zhao Wang , Di-Di Tang , Han-Yue Zhang , Xiao-Yue Ma , De-Hua Xing , Chenjiang Liu , Yu Xia , Yan Li","doi":"10.1039/d5qo00080g","DOIUrl":null,"url":null,"abstract":"<div><div>Visible-light-mediated 1,2-dicarbofunctionalization of alkenes provides a powerful tool for the synthesis of structurally complicated and diverse molecules from simple precursors in one step. In this work, photo-catalyzed three-component 1,2-alkylation of alkenes with alkylboronic pinacol esters (APEs) and aldehydes has been accomplished. This transition-metal-free protocol provided a clean and efficient way to access secondary alcohols, with wide substrate scope compatibility and good functional group tolerance, and it allowed a variety of alkenes, APEs and aldehydes to be transformed to the desired products in moderate to good yields under metal-free conditions. Mechanism studies disclosed that this transformation may involve a radical addition and radical–radical cross-coupling process.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 9","pages":"Pages 3035-3040"},"PeriodicalIF":0.0000,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-light-induced three-component radical cascade 1,2-dialkylation of alkenes to access alcohols†\",\"authors\":\"Yu-Zhao Wang , Di-Di Tang , Han-Yue Zhang , Xiao-Yue Ma , De-Hua Xing , Chenjiang Liu , Yu Xia , Yan Li\",\"doi\":\"10.1039/d5qo00080g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Visible-light-mediated 1,2-dicarbofunctionalization of alkenes provides a powerful tool for the synthesis of structurally complicated and diverse molecules from simple precursors in one step. In this work, photo-catalyzed three-component 1,2-alkylation of alkenes with alkylboronic pinacol esters (APEs) and aldehydes has been accomplished. This transition-metal-free protocol provided a clean and efficient way to access secondary alcohols, with wide substrate scope compatibility and good functional group tolerance, and it allowed a variety of alkenes, APEs and aldehydes to be transformed to the desired products in moderate to good yields under metal-free conditions. Mechanism studies disclosed that this transformation may involve a radical addition and radical–radical cross-coupling process.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 9\",\"pages\":\"Pages 3035-3040\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-02-27\",\"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/S2052412925001354\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/2/22 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/S2052412925001354","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/22 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Visible-light-induced three-component radical cascade 1,2-dialkylation of alkenes to access alcohols†
Visible-light-mediated 1,2-dicarbofunctionalization of alkenes provides a powerful tool for the synthesis of structurally complicated and diverse molecules from simple precursors in one step. In this work, photo-catalyzed three-component 1,2-alkylation of alkenes with alkylboronic pinacol esters (APEs) and aldehydes has been accomplished. This transition-metal-free protocol provided a clean and efficient way to access secondary alcohols, with wide substrate scope compatibility and good functional group tolerance, and it allowed a variety of alkenes, APEs and aldehydes to be transformed to the desired products in moderate to good yields under metal-free conditions. Mechanism studies disclosed that this transformation may involve a radical addition and radical–radical cross-coupling process.