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

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. A series of glucoside-based imidazolium salts (Glu-IMSs) combining glucoside and imidazolium head groups with different substituents were synthesized. The catalytic activities of these Glu-IMSs were evaluated in Pd-catalyzed Heck–Mizoroki (19 examples) and Suzuki–Miyaura (15 examples) reactions in water media. Glu-IMSs with –OH and NHCs two coordination sites was found to be most efficient ligand among them. HR-TEM analysis showed that in the presence of Glu-IMSs in water, palladium nanoparticles was formed with an average size of around 4.0 nm, the generation of Pd(0) nanoparticles would act as efficient real catalytic species to accelerate the cross coupling reaction in water media. [Display omitted] •Preparation of Glu-IMSs from commercial N-substituent imidazole.•The catalytic activities of Pd/Glu-IMSs were evaluated with Heck–Mizoroki and Suzuki–Miyaura reactions in water.•Glu-IMSs with –OH and NHCs two coordination sites was the most efficient ligand.•The Glu-IMSs stabilized Pd NPs with an average size of ~4.0 nm.•A series novel fluorine-cored OFMs were synthesized.