{"title":"无金属膦催化的可见光诱导的烯自由基环化:获得环状宝石-二氟酰基支架","authors":"Ruowen Li, Yicong Li, Yiwei Liu, Yanzhao Wang, Jingjing Wu and Fanhong Wu","doi":"10.1039/D4QO00503A","DOIUrl":null,"url":null,"abstract":"<p >In this study, we developed the first visible-light-induced phosphine-catalyzed radical cyclization of bromodifluoroacyl arenes with diverse alkenes, affording a variety of cyclic <em>gem</em>-difluoroacyl scaffolds in good to excellent yields. The strategy is highlighted by metal photocatalyst-free nature, mild reaction conditions and excellent functional group tolerance, and it is amenable to late-stage modification of complex molecules and gram-scale synthesis, and expands the reaction profiles of phosphine catalysis. Preliminary experimental and computational studies indicate that this reaction involves a radical process that is triggered by the photochemical activity of an electron donor–acceptor complex formed from bromodifluoroacyl and phosphine.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Metal-free phosphine-catalyzed visible-light-induced radical cyclization of alkenes: access to cyclic gem-difluoroacyl scaffolds†\",\"authors\":\"Ruowen Li, Yicong Li, Yiwei Liu, Yanzhao Wang, Jingjing Wu and Fanhong Wu\",\"doi\":\"10.1039/D4QO00503A\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >In this study, we developed the first visible-light-induced phosphine-catalyzed radical cyclization of bromodifluoroacyl arenes with diverse alkenes, affording a variety of cyclic <em>gem</em>-difluoroacyl scaffolds in good to excellent yields. The strategy is highlighted by metal photocatalyst-free nature, mild reaction conditions and excellent functional group tolerance, and it is amenable to late-stage modification of complex molecules and gram-scale synthesis, and expands the reaction profiles of phosphine catalysis. Preliminary experimental and computational studies indicate that this reaction involves a radical process that is triggered by the photochemical activity of an electron donor–acceptor complex formed from bromodifluoroacyl and phosphine.</p>\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-05-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00503a\",\"RegionNum\":1,\"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 Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00503a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Metal-free phosphine-catalyzed visible-light-induced radical cyclization of alkenes: access to cyclic gem-difluoroacyl scaffolds†
In this study, we developed the first visible-light-induced phosphine-catalyzed radical cyclization of bromodifluoroacyl arenes with diverse alkenes, affording a variety of cyclic gem-difluoroacyl scaffolds in good to excellent yields. The strategy is highlighted by metal photocatalyst-free nature, mild reaction conditions and excellent functional group tolerance, and it is amenable to late-stage modification of complex molecules and gram-scale synthesis, and expands the reaction profiles of phosphine catalysis. Preliminary experimental and computational studies indicate that this reaction involves a radical process that is triggered by the photochemical activity of an electron donor–acceptor complex formed from bromodifluoroacyl and phosphine.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.