An efficient strategy for the formation of alkenyl-functionalized spirocarbocyclic scaffolds from al-kyne-containing phenol-based biaryls via sequential iodine-induced cyclization/dearomatization and Pd-catalyzed coupling of N-tosylhydrazones is devel-oped.The approach provides various spirocarbocyclic compounds in moderate to excellent yields with good functional tolerance.The results also demonstrate the feasibility for the direct cross-couplings of N-tosylhydrazones with sterically congested tetrasubstituted alkenyl halides.