perfluoropyridylation of indoles via reaction of perfluorinated pyridines with indole compounds

The reaction of perfluoropyridines with indoles and bis(indolyl)methanes (bims) was investigated. the aromatic nucleophilic substitution of pentafluoropyridine with indoles occurs at the 4-position of pyridine ring by nitrogen site of indolyl anion, while reaction with 2,3,5,6-tetrafluoro-4-(phenylsulfonyl)pyridine gave a mixture of products arising substitution at 2-position of pyridine ring and replacement of phenylsulfonyl group. furthermore, the reaction of pentafluoropyridine with bims yielded mixture of mono- and bis-perfluoropyridyl products.