Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions

Fluoro-substituted aliphatic nitriles are shown to undergo the Houben–Hoesch reactions with arenes in CF3SO3H to give fluoro-substituted ketones in good yields. The fluorine substituents appear to enhance the reactivities of the nitriles (and the nitrilium ion intermediates) compared to similar aliphatic nitriles. Fluoro-substituted ketones are also shown to be accessible through the reactions of organometallic reagents and fluoro-substituted nitriles.