We report the Cu-catalyzed SF4-alkynylation of quinolones, chromones, and cyclohexenones using pyridyl SF4-alkynes under Lewis acid assisted conditions, affording diverse SF4-linked heterocycles in good to high yields. The method leverages the electron-deficient, enone-like character of SF4-alkynes while maintaining broad functional group tolerance. Notably, the SF4 unit remains stable under oxidative and acidic conditions, enabling efficient ring-reconstruction from six- to five-membered heterocycles. This strategy provides access to regulation-friendly fluorinated scaffolds with significant potential in medicinal chemistry.