{"title":"Aerobic Reconstruction of Amines to Amides: A C–N/C–C Bond Cleavage Approach","authors":"Qinyue Tao, Yanling Zheng, Qiang Li, Yang Long, Jing Wang, Zewei Jin, Xiangge Zhou","doi":"10.1021/acs.orglett.4c04366","DOIUrl":null,"url":null,"abstract":"Herein, an aerobic reconstruction of amines to amides via C(sp<sup>3</sup>)–N bond and C(sp<sup>2</sup>)–C(sp<sup>3</sup>) bond cleavage is described. This method features a metal-free reaction, insensitivity to oxygen or moisture, and ambient air as the terminal oxidant. Preliminary mechanistic studies suggest that the reaction pathway of amine oxidation, followed by imine exchange and Beckmann rearrangement, is involved.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-16","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.4c04366","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
Herein, an aerobic reconstruction of amines to amides via C(sp3)–N bond and C(sp2)–C(sp3) bond cleavage is described. This method features a metal-free reaction, insensitivity to oxygen or moisture, and ambient air as the terminal oxidant. Preliminary mechanistic studies suggest that the reaction pathway of amine oxidation, followed by imine exchange and Beckmann rearrangement, is involved.
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.