Trifluoroacetaldehyde <i>N</i>-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom–Hydrogen Bond

Abstract

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 <i>N</i>-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 <i>N</i>-tosylhydrazone revealed its wide applicability in the synthesis of trifluoroethyl-containing substances.