Zhendong Cheng , Weiwei Xu , Xuliang Tan , Zhengrui Zhou , Liwei Zhou , Yun Liang , Yuan Yang
{"title":"C–H silylation and boronation enabled by alkyne insertion/vinyl to aryl 1,5-palladium migration†","authors":"Zhendong Cheng , Weiwei Xu , Xuliang Tan , Zhengrui Zhou , Liwei Zhou , Yun Liang , Yuan Yang","doi":"10.1039/d4qo02224f","DOIUrl":null,"url":null,"abstract":"<div><div>1,<em>n</em>-Metal migration represents a powerful strategy for C–H functionalization that is otherwise difficult to achieve. Nevertheless, catalytic reactions involving 1,5-palladium migration have rarely been reported so far. Herein, an alkyne insertion/vinyl to aryl 1,5-palladium migration strategy has been disclosed for the α-C–H silylation and boronation of a naphthalene ring, thus achieving the transformation of alkyne-tethered naphthalene bromides to silylated and boronated benzo[<em>f</em>]isoquinolines and benzo[<em>f</em>]isochromenes in moderate to excellent yields.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1491-1497"},"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/S2052412924009008","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
1,n-Metal migration represents a powerful strategy for C–H functionalization that is otherwise difficult to achieve. Nevertheless, catalytic reactions involving 1,5-palladium migration have rarely been reported so far. Herein, an alkyne insertion/vinyl to aryl 1,5-palladium migration strategy has been disclosed for the α-C–H silylation and boronation of a naphthalene ring, thus achieving the transformation of alkyne-tethered naphthalene bromides to silylated and boronated benzo[f]isoquinolines and benzo[f]isochromenes in moderate to excellent yields.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
