Ni-Catalyzed C(sp2)–H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as structurally diverse alkyl sources

Abstract

A Ni-catalyzed direct C–H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors is described. The reaction forms a new C(sp³)–C(sp²) bond via the selective cleavage of both C(sp³)–C(sp³) and C(sp²)–H bonds. This transformation shows a high functional-group tolerance and, due to the structural diversity of alkylsilyl peroxides, a wide range of alkyl chains including functional groups and complex structures can be introduced at the ortho-position of readily available N-quinolylbenzamide derivatives. Mechanistic studies suggest that the reaction involves a radical mechanism.