Abstract

Contrary to a literature claim, 2,6-difluoropyridine-3-carboxaldehyde can be readily prepd. by consecutive treatment of 2,6-difluoropyridine with lithium diisopropylamide and N,N-dimethylformamide. Regioselective displacements of fluorine from the aldehyde by nucleophiles were carried out. To demonstrate the versatility of the organometallic approach, some two dozens of further 2,6-difluoropyridine derivs. were prepd. applying a combination of modern organometallic methods such as site selective hydrogen/metal and halogen/metal permutations and deprotonation-triggered heavy halogen migrations. [on SciFinder (R)]

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