Condensation of αβ-unsaturated amines with perfluoroarenes

Abstract

Condensation of αβ-unsaturated amines (enamines, keten ON-acetals, ynamines) with perfluoroarenes (perfluorobenzene, perfluorotoluene, bromopentafluorobenzene, perfluoropyridine) leads to the formation of ketones, esters, and amines α-substituted by a perfluoroaryl group. In the case of enamines, C-arylation can be followed by intramolecular N-arylation, giving fluorinated tetrahydrocarbazoles which can then be dehydrogenated by chloranil to give fluorinated carbazoles.