Catalyst-Controlled Regiodivergent C–H Arylation Site of Fluorinated 2-Arylpyridine Derivatives: Application to Luminescent Iridium(III) Complexes

Abstract

Regiodivergent C–H bond arylation of fluorinated 2-arylpyridines and 2-arylquinolines has been developed. The use of Pd catalyst allows functionalization of the C–H bond of the aryl flanked by two fluorine atoms (most acidic position), while using Ru catalyst, the arylation takes place on the aryl unit at the ortho position of the heterocycle. Both reaction conditions exhibit a good functional group tolerance. The synthetically useful selectivity observed with Pd catalyst was applied to design C^N ligands for the preparation of luminescent cationic iridium(III) complexes. The influence of the incorporated aryl group onto the fluorinated phenyl unit and the fluorine position patterns on the photophysical properties is described.