This study demonstrates quick access to heteroatom-embodied complex fused polycyclic frameworks through a palladium-catalyzed domino process facilitated by microwave-assisted crossover annulation of o-alkynylarylhalides and dihydrobenzofurans derivatives. The overall success of this process lies in the careful design of dihydrobenzofuran precursors that direct the initial palladium-mediated annulation step to proceed in a highly regioselective manner to furnish a single regioisomeric product. Notably, this one-pot method has witnessed good substrate scope and has furnished products with excellent yields.