Cu-Catalyzed Three-Component Carboamination of Electron Deficient Olefins

The copper-catalyzed three-component carboamination of atropates for the synthesis of α-aryl amino acid derivatives is presented. The scope of the reaction is explored with respect to all three coupling partners: the alkyl halide, the atropate, and the aryl amine. A total of 41 examples are included, with yields of ≤92%. Both primary and secondary aryl amines participate in the carboamination along with α-haloesters, nitriles, and perfluoroiodoalkanes. Mechanistic investigations support a radical mechanism involving Cu-mediated C–N bond formation with the radical adduct.本工作报道了铜催化阿托酸酯（atropates）参与的三组分碳胺化反应（carboamination）合成α-芳基氨基酸衍生物的方法。本研究针对该反应的三类偶联底物——烷基卤代物、阿托酸酯与芳基胺——展开了系统的底物范围考察，共收录41个反应实例，产率最高可达92%。一级与二级芳基胺均可参与该碳胺化反应，底物涵盖α-卤代酯、腈类以及全氟碘代烷烃。机理研究结果支持该反应遵循自由基机理，涉及铜介导的自由基加合物参与的C-N键构建过程。