Convenient synthesis of α-perfluoroaryl and α-perfluorohetaryl substituted α-aminomethanephosphonates

Potassium salt of diethyl (diphenylmethyleneamino)methanephosphonate reacts with pentafluoropyridine, octafluorotoluene, diethoxymethylpentafluorobenzene, or octafluoronaphthalene to afford, on product hydrolysis, the corresponding α-perfluoro(het)aryl substituted derivatives in high yield and regioselectivity. The method provides a new prospective route to fluorinated α-aminophosphonates. In the case of N-benzylidenepentafluoroaniline the outcome of the reaction is different and results in the formation of diethyl (pentafluorophenyl)amidophosphate.