Cooperative Pd/Cu Catalysis: Multicomponent Synthesis of Tetrasubstituted Imidazolones from Methyl a-lsocyanoacetates, Primary Amines, and Aryl(vinyl) Iodides

Three-component reaction of methyl alpha,alpha-disubstituted alpha-isocyanoacetates, primary amines, and aryl(vinyl) halides in the presence of 0 Pd(OAc)(2) (0.05 equiv) and Cu2O (1.0 equiv) provided 2,3,5,5-tetrasubstituted imidazolones via the formation of three chemical bonds. A copper -mediated migratory insertion of the isocyano group into the N-H bond of the amine followed by lactamization and Pd-catalyzed cross-coupling of the in situ generated amidinyl copper species with aryl(vinyl) halides accounted for the reaction outcome.