{"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":"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.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"85 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo02224f","RegionNum":1,"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
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.
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.
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