Ionic Liquids Based on Oxidoperoxido-Molybdenum(VI) Complexes with a Chelating Picolinate Ligand for Catalytic Epoxidation

Abstract

Ionic oxidoperoxido-molybdenum(VI) complexes of the type [Cat][MoO(O2)2(pic)], with pic = N,O-chelated picolinate ligand and Cat = monocation, were prepared in high yields (82–95%) from the precursor complex [H3O][MoO(O2)2(pic)] via [H]+ cation exchange for 1-ethyl-3-methylimidazolium [EMIM]+, 1-butyl-3-methylimidazolium [BMIM]+, 1-octyl-3-methylimidazolium [OMIM]+, N-cetylpyridinium [C16Py]+, and N-methyl-N,N,N-trioctylammonium [Aliquat]+. The structure and purity of the ionic compounds were assessed by 1H and 13C NMR, FT-IR, and elemental analysis (C, H, N), and the electrochemical properties were studied by differential pulse voltammetry (DPV) and cyclic voltammetry (CV). The [Cat][MoO(O2)2(pic)] compounds showed promising catalytic epoxidation activity based on the model reaction of cis-cyclooctene with tert-butyl hydroperoxide as oxidant. The type of cation influenced the physical state of the compound and the catalytic performance.