our proposed novel strategy addresses the following challenges: a) It enables the direct synthesis of alkylidene-based bis-heterocyclic scaffolds through a transition metal-catalyzed C−H functionalization, followed by a novel DG migration and an extrinsic cyclization pathway. b) This methodology provides new opportunities to explore unsymmetrical alkyne compounds. c) Additionally, we anticipate that this approach will effectively overcome challenges related to chemo-, regio-, and stereoselectivity. d) Furthermore, we expect the desired molecules to have broad applications in the fields of chemical biology and medicinal chemistry. e) Finally, the methodology operates in a step- and atom-economic manner, which aligns with green and sustainable principles, making it highly relevant for environmentally conscious synthetic methodologies.