A method for the generation of trifluoromethylated β-keto diazos and their applications in intramolecular Appel type reactions are reported. The key success of this reaction is a diazo species as an N-nucleophile in Appel reactions. This reaction is conducted under mild conditions and has a broad substrate scope, affording trifluoromethylpyrazoles in ≤94% yields. This protocol represents a new type of Appel reaction and also a new reaction mode of fluoro diazoalkanes.