Cheng Huang, Zhong-Ming Ye, Yu-Shu Qin, Gui-Ping You, Zhenhong Wei, Hu Cai
{"title":"Radical α-C–H Alkylation and Heteroarylation of Benzyl Anilines Enabled by Organic Photoredox Catalysis","authors":"Cheng Huang, Zhong-Ming Ye, Yu-Shu Qin, Gui-Ping You, Zhenhong Wei, Hu Cai","doi":"10.1021/acs.orglett.4c04278","DOIUrl":null,"url":null,"abstract":"A photocatalysis-involved α-amino radical provides an appealing approach for rapid construction of complex amine architectures. Reported herein is an organophotoredox catalytic approach to α-C–H alkylation and heteroarylation of benzyl anilines, which enables the introduction of valuable trifluoromethyl alcohol, chromanone, or pyridine motifs at the α position of amines. This protocol highlights metal-free, step and atom economies and broad substrate scopes (>80 examples). Control experiments and electron paramagnetic resonance spectroscopy identified the α-amino radical derived from the α-amino C–H bond.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-17","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.4c04278","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 photocatalysis-involved α-amino radical provides an appealing approach for rapid construction of complex amine architectures. Reported herein is an organophotoredox catalytic approach to α-C–H alkylation and heteroarylation of benzyl anilines, which enables the introduction of valuable trifluoromethyl alcohol, chromanone, or pyridine motifs at the α position of amines. This protocol highlights metal-free, step and atom economies and broad substrate scopes (>80 examples). Control experiments and electron paramagnetic resonance spectroscopy identified the α-amino radical derived from the α-amino C–H bond.
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.