PALLADIUM-CATALYZED HYDROXYCARBONYLATION OF VINYL AND ARYL TRIFLATES - SYNTHESIS OF ALPHA,BETA-UNSATURATED AND AROMATIC CARBOXYLIC-ACIDS

The palladium-catalyzed hydroxycarbonylation of vinyl and aryl triflates, under a CO balloon, in the presence of potassium acetate affords alpha,beta-unsaturated and aromatic carboxylic acids with one more carbon in good to high yield. The nature of the solvent and of the ligand have been proved to be crucial for the success of the reaction. Vinyl triflates undergo the hydroxycarbonylation at room temperature in DMF in the presence of Pd(OAc)2(PPh3)2. Aryl triflates produce best results at 60-degrees-C in DMSO in the presence of Pd(OAC)2 and 1,1-bis (diphenylphosphino)ferrocene (dppf).