{"title":"Ti-Catalyzed Functional Group Tolerant and Regioselective Cross Couplings of (Hetero)aryl Grignard Reagents with Halopyridines.","authors":"Jin-Long Zhao,Jun-Ting Li,Jing-Yan Kong,Xin-Fang Duan","doi":"10.1021/acs.orglett.5c02166","DOIUrl":null,"url":null,"abstract":"We report an unprecedented Ti-catalyzed functional group tolerant and regioselective coupling reaction where (hetro)aryl Grignard reagents are coupled with halopyridines and haloquinolines through an SRN pathway. A simple titanate catalyst not only triggered radical anion generation and the corresponding SRN couplings but also enabled high functional group tolerance and regioselectivity. Highly electron-deficient functionalized Grignard reagents were quite involved in such reactions, and a variety of valuable arylpyridines, bipyridines, and terpyridines were assembled facilely.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c02166","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
We report an unprecedented Ti-catalyzed functional group tolerant and regioselective coupling reaction where (hetro)aryl Grignard reagents are coupled with halopyridines and haloquinolines through an SRN pathway. A simple titanate catalyst not only triggered radical anion generation and the corresponding SRN couplings but also enabled high functional group tolerance and regioselectivity. Highly electron-deficient functionalized Grignard reagents were quite involved in such reactions, and a variety of valuable arylpyridines, bipyridines, and terpyridines were assembled facilely.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.