Yong Yuan, Feng Zhang, Xincong Liu, Chunyan Bai, Hangfei Jiang, Xiazhen Bao, Dongsheng Ji, Congde Huo
{"title":"Electrochemical Aminooxygenation of Enamides.","authors":"Yong Yuan, Feng Zhang, Xincong Liu, Chunyan Bai, Hangfei Jiang, Xiazhen Bao, Dongsheng Ji, Congde Huo","doi":"10.1021/acs.orglett.5c00005","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we present an unprecedented electrochemical approach for aminooxygenation of enamides with azoles under transition-metal- and oxidizing-reagent-free conditions. This method affords 4-azolated oxazolines directly from readily available starting materials in up to 95% yield. Central to our success is the utilization of electrical energy as the primary driving force and NaBr as a mediator. Importantly, the resulting 4-azolated oxazolines exhibit potential utility as ligands (pyrazole-oxazoline ligands) in transition-metal-catalyzed reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-13","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.5c00005","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Herein, we present an unprecedented electrochemical approach for aminooxygenation of enamides with azoles under transition-metal- and oxidizing-reagent-free conditions. This method affords 4-azolated oxazolines directly from readily available starting materials in up to 95% yield. Central to our success is the utilization of electrical energy as the primary driving force and NaBr as a mediator. Importantly, the resulting 4-azolated oxazolines exhibit potential utility as ligands (pyrazole-oxazoline ligands) in transition-metal-catalyzed reactions.
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.