Cu-Catalyzed Three-Component Carboamination of Electron Deficient Olefins

The copper-catalyzed three-componentcarboamination of atropatesfor the synthesis of & alpha;-aryl amino acid derivatives is presented.The scope of the reaction is explored with respect to all three couplingpartners: the alkyl halide, the atropate, and the aryl amine. A totalof 41 examples are included, with yields of & LE;92%. Both primaryand secondary aryl amines participate in the carboamination alongwith & alpha;-haloesters, nitriles, and perfluoroiodoalkanes. Mechanisticinvestigations support a radical mechanism involving Cu-mediated C-Nbond formation with the radical adduct.

Automated summary

This study presents the copper-catalyzed three-componentcarboamination of atropates for the synthesis of α-aryl amino acid derivatives. The reaction scope 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.