Xin Li , Yan Jiao , Lifei Han , Jinwei Sun , Xuan Zhang
{"title":"1-三氟甲基烯烃与黄原酸酯盐的可见光诱导脱氧衍生的烷基的脱氟烷基化:宝石二氟烯烃的合成†","authors":"Xin Li , Yan Jiao , Lifei Han , Jinwei Sun , Xuan Zhang","doi":"10.1039/d3ob00333g","DOIUrl":null,"url":null,"abstract":"<div><p>Catalyst- and metal-free difluoroallylation of alkyl precursors with trifluoromethyl alkenes for the synthesis of <em>gem</em>-difluoroalkenes is appealing and challenging. We herein describe a visible light-induced approach that enables deoxygenative difluoroallylation of abundant alcohols <em>via</em> xanthate salts with trifluoromethyl alkenes, where xanthate salts work as a photoreductant and an alkylating reagent, avoiding the use of external catalysts. This one-pot method can accommodate primary, secondary and tertiary alcohols with good functionality tolerance and be successfully applied to the late-stage functionalization of natural products and drugs.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"21 16","pages":"Pages 3330-3334"},"PeriodicalIF":2.9000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Defluorinative alkylation of 1-trifluoromethyl alkenes with alkyl radicals derived from visible light-induced deoxygenation of xanthate salts: synthesis of gem-difluoroalkenes†\",\"authors\":\"Xin Li , Yan Jiao , Lifei Han , Jinwei Sun , Xuan Zhang\",\"doi\":\"10.1039/d3ob00333g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Catalyst- and metal-free difluoroallylation of alkyl precursors with trifluoromethyl alkenes for the synthesis of <em>gem</em>-difluoroalkenes is appealing and challenging. We herein describe a visible light-induced approach that enables deoxygenative difluoroallylation of abundant alcohols <em>via</em> xanthate salts with trifluoromethyl alkenes, where xanthate salts work as a photoreductant and an alkylating reagent, avoiding the use of external catalysts. This one-pot method can accommodate primary, secondary and tertiary alcohols with good functionality tolerance and be successfully applied to the late-stage functionalization of natural products and drugs.</p></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"21 16\",\"pages\":\"Pages 3330-3334\"},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052023000319\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052023000319","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Defluorinative alkylation of 1-trifluoromethyl alkenes with alkyl radicals derived from visible light-induced deoxygenation of xanthate salts: synthesis of gem-difluoroalkenes†
Catalyst- and metal-free difluoroallylation of alkyl precursors with trifluoromethyl alkenes for the synthesis of gem-difluoroalkenes is appealing and challenging. We herein describe a visible light-induced approach that enables deoxygenative difluoroallylation of abundant alcohols via xanthate salts with trifluoromethyl alkenes, where xanthate salts work as a photoreductant and an alkylating reagent, avoiding the use of external catalysts. This one-pot method can accommodate primary, secondary and tertiary alcohols with good functionality tolerance and be successfully applied to the late-stage functionalization of natural products and drugs.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.