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

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(sp(3))-C(sp(2)) bond via the selective cleavage of both C(sp(3))-C(sp(3)) and C(sp(2))-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.

Automated summary

This study describes a Ni-catalyzed direct C-H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors. The reaction forms a new C(sp(3))-C(sp(2)) bond via selective cleavage of both C(sp(3))-C(sp(3)) and C(sp(2))-H bonds. 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.