Copper-Catalyzed Suzuki Cross-Coupling Reaction Of Benzyl Electrophilc Reagents And Aryl-boron Compounds

Transition-metal catalyzed cross-coupling reaction is an efficient strategy of forming carbon-carbon bonds. Due to the superior features of organoboron compounds, such as easy manipulation, ready availability, cheap price and good stability, Suzuki reaction is widely used in organic synthesis. The Suzuki cross-coupling reactions have been developed with the wide substrate scope, the mild condition, and easy post processing. Palladium, nickel, copper are main transition metal catalysts in Suzuki cross-coupling reaction. Compared with palladium and nickel catalysts, Copper catalysts have irreplaceable practical meaning in Suzuki cross-coupling reaction with the features of low toxicity, inexpensive price and good stability.In this thesis copper-catalyzed Suzuki cross-coupling reaction of benzyl halides with arylboronates was described. This reaction has been developed for the first time. It was found that copper iodide could efficiently catalyze the reaction of benzyl chlorides and bromides with arylboronates, using diketone family ligands and N-methylcaprolactam as solvent. Furthermore, the reaction was conducted at60℃with excellent functional group compatibility.The reaction of secondary benzyl halides with arylboronate was also investigated, more challenging partners-secondary benzyl halides with β hydrogens or extra steric hindrance performed well with such catalytic system, and got moderate yield. This methodology provides a fruitful and efficient synthesis for functionalized diarylmethanes, diarylethanes and triarylmethanes, simultaneously complements nickel-and palladium-catalyzed Suzuki-Miyaura reaction.