Directing Group Migration Strategy: Ru(II)-Catalyzed Domino C-H Functionalization toward the Synthesis of 1,4-Dihydroisoquinolin-3(2H)-One Scaffolds.

Directing group (DG) migration strategies originating from transition-metal-catalyzed C-H functionalization have recently attracted considerable attention. Herein, we report a Ru(II)-catalyzed domino process that involves C-H functionalization, DG-migration, and a subsequent 1,6-aza-conjugate addition between N-carbamoyl indoles and alkynylated p-quinone methides (p-QMs), providing an efficient route to 1,4-dihydroisoquinolin-3(2H)-one-based bisheterocycles. Notably, the protocol exhibits a broad substrate scope, delivers moderate to excellent yields, and is amenable to late-stage functionalization of structurally diverse biologically active molecules and natural products.