Manganese(II)/Picolinic Acid Catalyst System for Epoxidation of Olefins

Article abstract of DOI:10.1021/acs.orglett.6b00518

An in situ generated catalyst system based on Mn(CF₃SO₃)₂, picolinic acid, and peracetic acid converts an extensive scope of olefins to their epoxides at 0 °C in <5 min, with remarkable oxidant efficiency and no evidence of radical behavior. Competition experiments indicate an electrophilic active oxidant, proposed to be a high-valent Mn = O species. Ligand exploration suggests a general ligand sphere motif contributes to effective oxidation. The method is underscored by its simplicity and use of inexpensive reagents to quickly access high value-added products.