Selective Michael Additions of Primary and Secondary Amines to Perfluoroalkylated Sulfoxides and Sulfones as a Tool for Fluorous Tagging

Vinyl tridecafluorohexyl sulfoxide 1 and sulfone 2 are shown to be highly reactive towards Michael addition with a broad range of secondary and primary amines. Full selectivity for monofunctionalization of primary amines can be achieved by a proper choice of reagent 1 or 2 depending on amine basicity.