{"title":"Ligand-Controlled C2- or C3-Selectivity Switching in the Palladium-Catalyzed C–H Arylation of Nonsubstituted 1H-Pyrrole","authors":"Miyuki Yamaguchi, Kenichi Nakai, Kiho Morioka, Ayano Sato, Sakiko Fujiwara, Hideyuki Konishi, Kei Manabe","doi":"10.1021/acs.orglett.4c04085","DOIUrl":null,"url":null,"abstract":"The C2- or C3-selective direct C–H arylation of nonsubstituted 1<i>H</i>-pyrrole with aryl chlorides/nonaflates was achieved using catalysts derived from palladium and appropriate phosphine ligands. The site selectivity of the arylation can be switched by changing the ligands, and the C3-selective arylation of nonsubstituted 1<i>H</i>-pyrrole was realized for the first time. <i>t</i>BuOLi played an important role in suppressing N-arylation and accelerating C2- or C3-arylation.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"46 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-30","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.4c04085","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
The C2- or C3-selective direct C–H arylation of nonsubstituted 1H-pyrrole with aryl chlorides/nonaflates was achieved using catalysts derived from palladium and appropriate phosphine ligands. The site selectivity of the arylation can be switched by changing the ligands, and the C3-selective arylation of nonsubstituted 1H-pyrrole was realized for the first time. tBuOLi played an important role in suppressing N-arylation and accelerating C2- or C3-arylation.
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.
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