A　copper-catalyzed　oxidative　annulation　of　sydnones　with　perfluorocarboxylic　anhydride　for　the　synthesis　of　3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones　is　developed.　A　diverse　array　of　3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones　are　prepared　with　good　yields　(＞73　examples,　yields　up　to　95%).　The　synthetic　utility　of　the　developed　protocol　was　demonstrated　by　gram-scale　synthesis,　and　the　synthetic　transformation　to　1,2,4-triazol-3-one　products.　A　mechanistic　study　suggests　that　the　reaction　proceeds　via　the　extrusion　of　carbon　dioxide　to　generate　the　hydrazide　intermediate,　which　then　undergoes　intramolecular　cyclization　and　oxidation.　©　2024　American　Chemical　Society.