Synthesis of CF3-containing α-alkynyl-α-aminophosphonates by Sonogashira cross-coupling reaction

An efficient route to new α-CF3-α-aminophosphonic acid derivatives bearing an arylalkynyl moiety at the α-carbon atom has been developed. The method is based on palladium-catalyzed cross-coupling of the corresponding α-propargyl (ethynyl) α-aminophosphonates with aryl iodides to afford the aminophosphonic acid derivatives with an internal triple bond that is suitable for further modifications.

Graphical abstractAn efficient route to new α-CF3-α-aminophosphonic acid derivatives bearing an arylalkynyl moiety at the α-carbon atom has been developed.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Pd-catalyzed cross-coupling of α-CF3-α-alkynyl-α-aminophosphonates with aryl iodides. ► New α-arylalkynyl-α-aminophosphonates were obtained in moderate to good yields. ► CF3-substituted homologous of P-phenylalanines were synthesized.