{"title":"Excited Pd-catalyzed dearomative 1,4-dicarbofunctionalization of nonactivated aromatic rings†","authors":"Kai Jiang , Ziyan Zhao , Xiaodong Yin , Fangjun Chen , Biaolin Yin","doi":"10.1039/d4qo02173h","DOIUrl":null,"url":null,"abstract":"<div><div>Excited-palladium catalysis has already been exploited to achieve 1,4-difunctionalization of dienes <em>via</em> the radical generation of an allylpalladium intermediate. Herein, nonactivated phenyl rings, which can be treated as masked trienes, have accomplished dearomative 1,4-dicarbofunctionalization in an excited-palladium catalyzed two- or three-component reaction system. A wide range of alkyl bromides and 1,3-dicarbonyl compounds, playing the roles of radical precursors and nucleophiles, respectively, were found to be suitable for this reaction. Various three-dimensional molecular architectures with multiple quaternary carbon centers were efficiently constructed by means of this mild reaction.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1579-1585"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-08","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/S205241292500004X","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
Excited-palladium catalysis has already been exploited to achieve 1,4-difunctionalization of dienes via the radical generation of an allylpalladium intermediate. Herein, nonactivated phenyl rings, which can be treated as masked trienes, have accomplished dearomative 1,4-dicarbofunctionalization in an excited-palladium catalyzed two- or three-component reaction system. A wide range of alkyl bromides and 1,3-dicarbonyl compounds, playing the roles of radical precursors and nucleophiles, respectively, were found to be suitable for this reaction. Various three-dimensional molecular architectures with multiple quaternary carbon centers were efficiently constructed by means of this mild reaction.