{"title":"区域和对映选择性镍催化非活化烯烃与邻苯二甲酸乙酯的氢胺化反应","authors":"Jia-Yi Li, , , Zhe-Xuan Li, , , Yue Liu, , , Yue Qiao, , and , Yan-Long Zheng*, ","doi":"10.1021/acscatal.5c05507","DOIUrl":null,"url":null,"abstract":"<p >Anthranils serve as versatile electrophilic amination agents for diverse C–N bond formations, yet achieving regioselective and enantioselective hydroamination of unactivated alkenes has remained a significant challenge. Herein, we report a NiH-catalyzed highly regio- and enantioselective hydroamination of unactivated alkenes with anthranils, providing a wide range of chiral amines bearing various functional groups and heterocyclic scaffolds in good yields with high enantioselectivities (72 examples, up to 97% yield and 99% ee). Both terminal and internal unactivated alkenes are compatible with this reaction, and good functional tolerance and mild conditions allow a late-stage hydroamination reaction of various biologically active molecule-derivatized alkenes and anthranils. Mechanistic studies support that the reaction proceeds via nickel-nitrenoid transfer.</p>","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"15 19","pages":"16622–16632"},"PeriodicalIF":13.1000,"publicationDate":"2025-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Regio- and Enantioselective Nickel-Catalyzed Hydroamination of Unactivated Alkenes with Anthranils\",\"authors\":\"Jia-Yi Li, , , Zhe-Xuan Li, , , Yue Liu, , , Yue Qiao, , and , Yan-Long Zheng*, \",\"doi\":\"10.1021/acscatal.5c05507\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Anthranils serve as versatile electrophilic amination agents for diverse C–N bond formations, yet achieving regioselective and enantioselective hydroamination of unactivated alkenes has remained a significant challenge. Herein, we report a NiH-catalyzed highly regio- and enantioselective hydroamination of unactivated alkenes with anthranils, providing a wide range of chiral amines bearing various functional groups and heterocyclic scaffolds in good yields with high enantioselectivities (72 examples, up to 97% yield and 99% ee). Both terminal and internal unactivated alkenes are compatible with this reaction, and good functional tolerance and mild conditions allow a late-stage hydroamination reaction of various biologically active molecule-derivatized alkenes and anthranils. Mechanistic studies support that the reaction proceeds via nickel-nitrenoid transfer.</p>\",\"PeriodicalId\":9,\"journal\":{\"name\":\"ACS Catalysis \",\"volume\":\"15 19\",\"pages\":\"16622–16632\"},\"PeriodicalIF\":13.1000,\"publicationDate\":\"2025-09-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Catalysis \",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acscatal.5c05507\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acscatal.5c05507","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Regio- and Enantioselective Nickel-Catalyzed Hydroamination of Unactivated Alkenes with Anthranils
Anthranils serve as versatile electrophilic amination agents for diverse C–N bond formations, yet achieving regioselective and enantioselective hydroamination of unactivated alkenes has remained a significant challenge. Herein, we report a NiH-catalyzed highly regio- and enantioselective hydroamination of unactivated alkenes with anthranils, providing a wide range of chiral amines bearing various functional groups and heterocyclic scaffolds in good yields with high enantioselectivities (72 examples, up to 97% yield and 99% ee). Both terminal and internal unactivated alkenes are compatible with this reaction, and good functional tolerance and mild conditions allow a late-stage hydroamination reaction of various biologically active molecule-derivatized alkenes and anthranils. Mechanistic studies support that the reaction proceeds via nickel-nitrenoid transfer.
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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