Catalytic Regioselective Epoxide Ring Opening with Phenol Using Homogeneous and Supported Analogues of Dimethylaminopyridine

Abstract

The regioselective ring opening of terminal epoxides using phenolic nucleophiles is examined using dimethylaminopyridine (DMAP) as a soluble catalyst and solid catalysts based on silica, polymer, and magnetic nanoparticle solids functionalized with DMAP analogues. The homogeneous reaction proceeds to 94 % conversion while achieving 93 % regioselectivity in 2 h at 120 °C. DMAP efficiently catalyzes the ring-opening reaction of a variety of epoxides using different substituted phenols with high conversions and excellent regioselectivities. Of the heterogeneous catalysts, the polymeric catalyst is more active and recyclable than the magnetic nanoparticle and silica supported catalysts, which had comparable activity and recyclability.