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.

Graphical abstractThe first application of phosphoglycine Schiff bases in the reaction of nucleophilic aromatic substitution is disclosed. The method was found to be suitable for preparing of α-perfluoro(het)aryl substituted aminomethanephosphonates.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► An easy access to α-perfluoro(het)aryl substituted α-aminophosphonates. ► Diethyl (diphenylmethyleneamino)methanephosphonate in nucleophilic aromatic substitution. ► Study on the scope and regioselectivity of the reaction.