Development of Pd/C-catalyzed Hydrogenative Removal Method of Phenolic Hydroxyl Groups

Abstract

Deoxygenation method of phenolic hydroxyl groups appears to be an important synthetic tool in the field of organic synthesis. Palladium-catalyzed reduction of perfluoroalkane sulfonates has arisen as an important method although the synthesis of perfluoroalkane sulfonates from the corresponding phenols can frequently be a major problem in terms of selectivity, stability and cost. Meanwhile we have recently reported Pd/C-Et₃N system smoothly catalyzes the hydrogenolysis of aryl halides. According to these results, the similar catalyst system should catalyze the hydrogenolysis of aryl mesylates. So we investigated the optimezed reaction conditions for the hydrogenolysis of the mesylate. The Pd/C–Et₂NH–H₂ system was found as an optimum catalyst for the hydrogenolysis.