Meizhong Tang , Ye Wang , Shenlin Huang , Lan-Gui Xie
{"title":"Stabilized carbon radical-mediated three-component polyfluoroalkylation of amino acid derivatives†","authors":"Meizhong Tang , Ye Wang , Shenlin Huang , Lan-Gui Xie","doi":"10.1039/d5qo00208g","DOIUrl":null,"url":null,"abstract":"<div><div>A three-component protocol for polyfluoroalkylation of amino acid derivatives has been developed. Captodatively stabilized carbon radical-mediated radical carbon–carbon bond formation facilitates the assembly of amino acid derivatives, styrenes and readily available polyfluoroalkyl sources. Various perfluoroalkyl and polyfluoroalkyl groups are demonstrated to be applicable for the derivation of amino acid compounds. Benzofuran and indole derivatives can also serve as components to ligate fluoroalkyl groups and amino acid derivatives, providing the possibility for dearomative dialkylation of biorelevant fragments.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 11","pages":"Pages 3373-3379"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-11","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/S2052412925001731","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A three-component protocol for polyfluoroalkylation of amino acid derivatives has been developed. Captodatively stabilized carbon radical-mediated radical carbon–carbon bond formation facilitates the assembly of amino acid derivatives, styrenes and readily available polyfluoroalkyl sources. Various perfluoroalkyl and polyfluoroalkyl groups are demonstrated to be applicable for the derivation of amino acid compounds. Benzofuran and indole derivatives can also serve as components to ligate fluoroalkyl groups and amino acid derivatives, providing the possibility for dearomative dialkylation of biorelevant fragments.