Trifluorination of Sulfides and Dithioketals Using IF5-Pyridine-HF.

Abstract Stable fluorinating reagent, IF5-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 IF5-pyridine-HF. Tetrafluorination of phenyl benzyl ketone and dibenzyl ketone dithioketals was also achieved by reaction with IF5-pyridine-HF and Et3N-6HF.