FLUORIDE ION-PROMOTED REACTION OF POLYFLUORO-1-PROPENYL P-TOLUENESULFONATE WITH AMINES - HIGHLY EFFICIENT AND GENERAL ACCESS TO (Z)-ALPHA-FLUORO-BETA-AMINO ACRYLALDEHYDES
2,3,3-Trifluoro-1-propenyl p-toluenesulfonate, readily available by dehydrofluorination of 2,2,3,3-tetrafluoropropyl p-toluenesulfonate, reacted smoothly with various primary or secondary amines in the presence of triethylamine and a catalytic amount of fluoride ion at ambient temperature for 3 h or at 70 degrees C for 1-2 h to afford the corresponding (Z)-alpha-fluoro-beta-(alkylamino- or -dialkylamino)acrylaldehydes in good to excellent yields, together with the formation of p-toluenesulfonyl fluoride.