A palladium-catalyzed annulation strategy for the synthesis of polycyclic heteroaromatic compounds incorporating a coumarin scaffold is developed. A key feature of this transformation is the use of a bidentate directing group composed of an amino and amide moiety, which enables precise control over periselective C-H activation and subsequent annulation. This robust protocol tolerates diverse coupling partners and delivers a broad range of π-extended, densely functionalized polycyclic frameworks