Can Yang, Lixing Shen, Ying Xie, Jianzhang Li*, Huanfeng Jiang and Wei Zeng*,
{"title":"Rh(III)-Catalyzed Indole Dearomative 1,2-Alkoxyl Shift Rearrangement","authors":"Can Yang, Lixing Shen, Ying Xie, Jianzhang Li*, Huanfeng Jiang and Wei Zeng*, ","doi":"10.1021/acs.orglett.5c0105110.1021/acs.orglett.5c01051","DOIUrl":null,"url":null,"abstract":"<p >A Rh(III)-catalyzed dearomative C3 alkoxylation of indoles via cascade C(sp<sup>2</sup>)–H activation and 1,2-alkoxyl shift rearrangement has been developed. This method provides an efficient strategy to rapidly assemble 3-alkoxyindolin-2-one scaffolds using alcohols as alkoxyl sources. Mechanistic studies indicate that indolyl C2 alkoxylation followed by Ag(I)/Cu(II)-mediated 1,2-alkoxyl migration is involved in this transformation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 15","pages":"4052–4056 4052–4056"},"PeriodicalIF":4.9000,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c01051","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
A Rh(III)-catalyzed dearomative C3 alkoxylation of indoles via cascade C(sp2)–H activation and 1,2-alkoxyl shift rearrangement has been developed. This method provides an efficient strategy to rapidly assemble 3-alkoxyindolin-2-one scaffolds using alcohols as alkoxyl sources. Mechanistic studies indicate that indolyl C2 alkoxylation followed by Ag(I)/Cu(II)-mediated 1,2-alkoxyl migration is involved in this transformation.
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.