Trifluorination of sulfides and dithioketals using IF5-pyridine-HF

Abstract Stable fluorinating reagent, IF 5 -pyridine-HF, was used for the polyfluorination of aryl alkyl sulfides. The introduction of three fluorine atoms with a concomitant migration of the arylsulfanyl group was achieved. Carrying out the reaction at 80 °C and presence of a methyl substituent on the aryl group were found to be effective for the polyfluorination. Trifluorinated products were also obtained from dithioketals by reaction with IF 5 -pyridine-HF. Tetrafluorination of phenyl benzyl ketone and dibenzyl ketone dithioketals was also achieved by reaction with IF 5 -pyridine-HF and Et 3 N-6HF.