Synthesis of glucoside-based imidazolium salts for Pd-catalyzed cross-coupling reaction in water

Abstract

Sugar-based imidazolium salts (IMSs) represent an outstanding type of material making them eye-catching for a wide variety of applications. Herein, a series of glucoside-based IMSs (Glu-IMSs) combining glucoside and imidazolium head groups with different substituents were synthesized. The catalytic activities of these Glu-IMSs were evaluated by Pd-catalyzed Heck-Mizoroki and Suzuki-Miyaura reactions in water. Among them, the Glu-IMSs contain both -OH and NHCs coordination sites was found to be the most efficient ancillary ligand in comparison with other Glu-IMSs with just single NHCs coordination site. The HR-TEM analysis showed that the palladium nanoparticles stabilized by the Glu-IMSs with an average size of ~4.0 nm was formed in the reaction system, which may be act as an efficient real catalytic species. Under the optimized reaction conditions, a series of novel fluorine-cored organic small molecule functional materials were synthesized with favorable yields.

Keywords: Cross-coupling reaction; Fluorine-cored functional materials; Imidazolium salts; Palladium catalysts; Sugar-based.