A　strategy　for　the　annulation　reaction　of　alkynones　with　ethyl　4,4,4-trifluoro-3-oxobutanoate　through　C-C　bond　cleavage　is　described.　The　zirconium-catalyzed　transformation　provides　access　to　a　wide　range　of　structurally　diverse　6-(trifluoromethyl)-2H-pyran-2-ones　in　moderate　to　good　yields,　utilizing　Na2CO3　as　a　base.　Further　transformations　into　trifluoromethylated　arene　derivatives　have　been　demonstrated　as　well.　Furthermore,　plausible　reaction　pathways　are　proposed　by　conducting　various　control　experiments　and　isolating　a　β-diketone　intermediate　(X-ray)　containing　an　intramolecular　hydrogen　bond.　©　2024　American　Chemical　Society.