Trifluoroacetaldehyde N-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom-Hydrogen Bond

Trifluorodiazoethane is a widely explored trifluoroethylating reagent, which is suitable for the preparation of a large number of fluorine-containing organic molecules. Nevertheless, CF3CHN2 has some disadvantages, such as volatility, storage instability, toxicity, and explosiveness. We report the application of trifluoroacetaldehyde N-tosylhydrazone as a CF3CHN2 precursor capable of generating in situ trifluorodiazoethane under mild basic conditions. Copper-catalyzed P-H, O-H, S-H, and C-H insertion reactions of trifluoroacetaldehyde N-tosylhydrazone revealed its wide applicability in the synthesis of trifluoroethyl-containing substances.