Xiao-Qian Zhang, Ningbo Li, Yongliang Zhang, Youliang Wang
{"title":"Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations","authors":"Xiao-Qian Zhang, Ningbo Li, Yongliang Zhang, Youliang Wang","doi":"10.1021/acs.orglett.5c00816","DOIUrl":null,"url":null,"abstract":"The [1,n]-hydride migration reactions represent one of the most powerful techniques to functionalize C(sp<sup>3</sup>)–H bonds and to rapidly construct molecular complexities. However, their substrates usually required multiple steps to prepare in advance. Herein, we developed a gold-catalyzed intermolecular coupling of hydride-donor-containing nucleophiles (amines) and hydride-acceptor-containing alkynes (1,3-diynamides) for cascade [1,5]-hydride migrations. Control experiments revealed the role of the dichloroethane solvent and the unexpected involvement of protonated anilines in promoting [1,5]-hydride migrations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"46 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-20","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.5c00816","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations
The [1,n]-hydride migration reactions represent one of the most powerful techniques to functionalize C(sp3)–H bonds and to rapidly construct molecular complexities. However, their substrates usually required multiple steps to prepare in advance. Herein, we developed a gold-catalyzed intermolecular coupling of hydride-donor-containing nucleophiles (amines) and hydride-acceptor-containing alkynes (1,3-diynamides) for cascade [1,5]-hydride migrations. Control experiments revealed the role of the dichloroethane solvent and the unexpected involvement of protonated anilines in promoting [1,5]-hydride migrations.
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.