Palladium-catalyzed three-component annulation reaction involving multiple C–H activation†

Abstract

The Pd-catalyzed ring-forming reaction via multiple C–H activation provides an efficient strategy to access cyclic ring systems. The current reactions are primarily restricted to single- and two-component reactions. Herein, we report a ring-forming reaction via palladium-catalyzed three-component multiple C–H activation. Using TsOMe as the methylating reagent, aryl iodides undergo maleimide-relayed C–H methylation. Subsequent cyclization via C(sp³)–H activation forms succinimide-fused tricyclic scaffolds. Depending on aryl iodides, the reaction involves dual or triple C–H activation to form two or three new C–C bonds. The reaction represents a new strategy for C–H methylation and offers a new synthetic method using simple and readily available substrates for succinimide-fused tricyclic scaffolds, which are crucial structural motifs found widely in organic compounds with diverse biological activities.