A regioselective coupling of ortho-heteroaryl anilines and 7-oxabenzonorbornadienes has been developed by leveraging free amine-directed redox-neutral Ru(II) catalysis. This protocol facilitates formal C-2 arylation of the indole moiety under mild conditions to offer valuable heterobiaryls in high yields. The reaction displays a broad substrate generality and scalability and retains efficacy in the presence of diverse pharmacophore scaffolds. Moreover, products bearing a free amine group were successfully employed in Mg(NTf 2 ) 2 -catalyzed double Michael addition cascade, which led to the synthesis of intricate indole-and pyrrole-fused azaheterocycles.