Palladium-Catalyzed Cross-Coupling Reaction And Synthesis Of The Containing Sulfur-Carbonyl Chiral Ligand Compound

Palladium and his compounds as a catalyst in organic synthesis, there are high catalytic performance, good selectivity, and less dosage, the wide range of application etc. And palladium catalyzed coupling reaction have been one of hot topics. Especially in recent years, the study on palladium catalyzed cross-coupling reaction is rapidly increasing, many new cross-coupling reactions have been reported. In this article, palladium acetate as catalyst, TBHP as oxidant and other conditions, diaryl ketones was synthesized by the cross dehydrogenation coupling reaction of 1-phenyl-1H-pyrazole derivatives with toluene derivatives and the reaction was studied and discussed.There are two major parts in this thesis:The first part of this thesis is literature review on palladium catalyzed cross-coupling reactions in recent years, and the present situation of research and development of the substrate ortho arylation reaction and the substrate ortho carbonylation reaction were briefly reviewed.The second part is experiment sections. Major work is as follows:1.Palladium catalyzed cross dehydrogenative coupling reaction of 1-phenyl-1H-pyrazole compounds. First we synthesized the staring substrate, we get 1-phenyl-1H-pyrazole compounds from the aromatic formaldehyde by a three-step reactions; Then under the condition of palladium acetate as the catalyst, TBHP as the oxidant,120℃, the starting substrates and the toluene undergo a cross dehydrogenative coupling reaction, to get the [(un)substitution phenyl](2-(3,5-disubstitution-1H-pyrazol-1-yl)phenyl) methanone for the first time, and we characterized the obtained compounds by 1HNMR,13CNMR, IR, MS.2. The synthesis of the containing sulfur-carbonyl chiral ligand compound chiral amino formic acid and ester and thiourea. First we synthesized the aryl isothiocyanates. Starting from the aryl amine and then by a two-step reaction, we get the aryl isothiocyanates; then under the mild condition,the aryl isothiocyanates reacted with quinine, menthol and (1S)-1-phenylethylamine to afford the chiral amino carbothioate and chiral thiourea, and we characterized the obtained compounds by 1HNMR,13CNMR,1R, MS.