Design of and Mechanistic Studies on a Biomimetic Iron–Imidazole Catalyst System for Epoxidation of Olefins with Hydrogen Peroxide

Abstract

Novel iron catalysts, both defined and in situ generated, for the epoxidation of aromatic and aliphatic olefins with hydrogen peroxide as terminal oxidant are described. Our catalyst approach is based on bio-inspired 1-aryl-substituted imidazoles in combination with cheap and abundant iron trichloride hexahydrate. We show that the free 2-position of the imidazole ligand motif plays a key role for catalytic activity, as substitution leads to a dramatic depletion of yield and conversion. X-ray studies, UV/Vis titrations, and NMR studies were carried out to clarify the mechanism.