Visible-Light-Induced Radical Cascade Cross-Coupling via C(sp3)-H Activation and C-N/N-O Cleavage: Feasible Access to Methylenebisamide Derivatives.

ABSTRACT

Here we report facile and manipulable access to methylenebisamide derivatives via visible-light-driven radical cascade processes incorporating C(sp3)-H activation and C-N/N-O cleavage. Mechanistic studies reveal that a traditional Ir-catalyzed photoredox pathway and a novel copper-induced complex-photolysis pathway are both involved, contributing to activating the inert N-methoxyamides and rendering the valuable bisamides. This approach exhibits many advantages, including mild reaction conditions, broad scope and functional group tolerance, and competitive step economy. Given the mechanistic plenitude and operational simplicity, we believe this package deal paves a promising way for the synthesis of valuable nitrogen-containing molecules.