Gold-catalyzed C3-H functionalization of quinoline N-oxides

Abstract Site-selective C-H functionalization of quinolines provides a direct way for the rapid construction and derivatization of pharmaceuticals, agrochemicals, and other biologically active compounds. Here we present a gold-catalyzed highly selective and redox-neutral C3-H functionalization of quinoline N-oxides, with indoles and tertiary anilines as nucleophiles for C-C coupling, while primary and secondary anilines give C-N coupling products. Experimental and computational mechanistic studies suggest that the gold-catalyzed C3-H functionalization of quinoline N-oxides undergoes C2-auration and subsequent concerted C3 nucleophilic addition.