{"title":"Visible-Light Driven Synthesis of Vinyl Amines without Photocatalyst","authors":"Koustav Pal, Debabrata Das, Krishna Gopal Ghosh, Devarajulu Sureshkumar","doi":"10.1021/acs.joc.4c01624","DOIUrl":null,"url":null,"abstract":"We developed a visible-light-induced vinyl amination of activated alkenes using TMSN<sub>3</sub> and CsF through EDA complex formation under an oxygen atmosphere. Without light, the EDA complex forms between activated alkene, CsF, and oxygen. Upon exposure to light, oxygen in the complex gets excited, initiating the HAT process. This method efficiently synthesizes vinyl-amine derivatives via a radical pathway, demonstrating good functional group tolerance and high yields in a short time. Further, the late-stage functionalization enables the synthesis of biologically active heterocycles.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01624","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We developed a visible-light-induced vinyl amination of activated alkenes using TMSN3 and CsF through EDA complex formation under an oxygen atmosphere. Without light, the EDA complex forms between activated alkene, CsF, and oxygen. Upon exposure to light, oxygen in the complex gets excited, initiating the HAT process. This method efficiently synthesizes vinyl-amine derivatives via a radical pathway, demonstrating good functional group tolerance and high yields in a short time. Further, the late-stage functionalization enables the synthesis of biologically active heterocycles.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.