Zhong-Sheng Nong, Pu-Sheng Wang, Qi-Lin Zhou, Liu-Zhu Gong
{"title":"Palladium-Catalyzed Branch-Selective Allylic C–H Amination Enabled by Nucleophile Coordination","authors":"Zhong-Sheng Nong, Pu-Sheng Wang, Qi-Lin Zhou, Liu-Zhu Gong","doi":"10.1021/acs.orglett.4c02935","DOIUrl":null,"url":null,"abstract":"Regiochemical control is a central subject in the field of synthetic chemistry. Here we unveil an innovative approach for the branch-selective allylic C–H amination of α-alkenes with amine nucleophiles facilitated by phosphoramidite–palladium catalysis. A diverse array of α-alkenes has been effectively utilized to produce a variety of structurally distinct allylamines with moderate to excellent regioselectivity. Furthermore, the asymmetric version of this reaction is feasible through the use of chiral phosphoramidite ligands, albeit with currently modest enantioselectivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-09-27","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.4c02935","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
Regiochemical control is a central subject in the field of synthetic chemistry. Here we unveil an innovative approach for the branch-selective allylic C–H amination of α-alkenes with amine nucleophiles facilitated by phosphoramidite–palladium catalysis. A diverse array of α-alkenes has been effectively utilized to produce a variety of structurally distinct allylamines with moderate to excellent regioselectivity. Furthermore, the asymmetric version of this reaction is feasible through the use of chiral phosphoramidite ligands, albeit with currently modest enantioselectivity.
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.