Palladium-catalyzed intramolecular C–H arylation of ferrocenyl-sulfides, sulfoxide and its application in metal ion recognition

Abstract

An intramolecular C–H arylation of ferrocenyl ortho-bromophenyl sulfide and sulfoxide has been developed with a palladium/non-chiral monophosphine ligand. Under mild reaction conditions, a wide range of ferrocene cyclosulfide and ferrocene cyclosulfoxide were obtained in up to 90 ​% yield. Moreover, planar chiral ferrocene cyclosulfide with enantioselectivities (up to 45 ​% ee) was synthesized utilizing chiral phosphine ligands. Furthermore, the compound 4a and 6a can be used as novel chemosensors to detect Cu²⁺ ion.