Catalytic Coupling Reaction Of Aromatic Boronic Acid With Allyl Ester By Palladium

We have demonstrated for the first time an effective catalytic system using palladium-catalyzed for carbonylation of aryl boronic acid allyl ester groups of the coupling reaction to α,β-unsaturatd ketones. The reaction uses an allyl acetate as electrophile, an aryl boronic acid as nucleophile, in the presence of CO, efficient completion of the carbonylation reaction to α,β-unsaturated ketones. We studied the effect for the reaction under the different catalysts, ligands, solvents, bases, and screen the temperature and the amount of water, too. Finally we get the optimal reaction conditions. Under the optimal conditions of the reaction, substrates were expanded, we find our primary product is the least substituted terminal α,β-unsaturated ketones, only a small amount of β,γ-unsaturated ketone obtained. We also made a detailed study of reaction mechanism.We used of acetic acid allyl esters and aryl boronic acid compounds in the carbonylation reaction with a palladium catalyzed reaction system, high yield and high selectivity has been achieved which overcomes the traditional preparation of α, β-unsaturated ketones harsh conditions, defects and poor reaction selectivity. The catalyzed reaction system shows a good prospect for α,β-unsaturated ketones.