Pan-Pan Li, Zhi Yang, Shao-Qun Cai, Wu Liang, Shi-Cui Fang, Jun-Fei Zhao, Bin Pan, Fei Du
{"title":"Palladium-Catalyzed and Photoinduced Site-Selective Alkynylation and Oxidation of the Remote C(sp3)–H","authors":"Pan-Pan Li, Zhi Yang, Shao-Qun Cai, Wu Liang, Shi-Cui Fang, Jun-Fei Zhao, Bin Pan, Fei Du","doi":"10.1021/acs.orglett.5c00271","DOIUrl":null,"url":null,"abstract":"A general and efficient method for the direct alkynylation and oxidation of remote C(sp<sup>3</sup>)–H bonds under photoirradiation is described. In this reaction, the Pd catalyst acts as both a photocatalyst to generate the nitrogen radical and a cross-coupling catalyst with a terminal alkyne. Attractive features of this system include good functional group tolerance, scalability, convenient reagents, and an operating system. The utility of this protocol is highlighted by its application for derivatization of several valuable aza-heterocycles such as caspase-3 inhibitor and azepinone derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"132 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-10","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.5c00271","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 general and efficient method for the direct alkynylation and oxidation of remote C(sp3)–H bonds under photoirradiation is described. In this reaction, the Pd catalyst acts as both a photocatalyst to generate the nitrogen radical and a cross-coupling catalyst with a terminal alkyne. Attractive features of this system include good functional group tolerance, scalability, convenient reagents, and an operating system. The utility of this protocol is highlighted by its application for derivatization of several valuable aza-heterocycles such as caspase-3 inhibitor and azepinone derivatives.
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.