The journey towards one-pot epoxidation-carboxylation reactions of alkenes

Abstract

Previously in the Kerton group [1], metal-containing ionic liquids have been investigated for the catalytic synthesis of cyclic carbonates from carbon dioxide and epoxides, which can be prepared via catalytic oxidation of alkenes. This has led to the attempt of a one-pot transformation of alkenes in cyclic carbonates using [BMIm]Cl and manganese salts. A number of parameters were examined in order to obtain optimized conditions for the H₂O₂-mediated epoxidation of alkenes. This has lead to exciting results for the conversion of styrene to styrene carbonate. Investigation then turned towards the synthesis of bis(amide) compounds, that when paired with a suitable metal, might yield catalysts suitable for one-pot epoxidation-carboxylation reactions. This is based off stable oxidation catalysts such as the TAML-Fe complexes developed by Collins and co-workers [2]. Their stability has been attributed to not only the macrocyclic nature of the ligand but also its amide backbone. Adolph et al. [3] also recently reported success in using amide-containing ligands in the catalytic formation of cyclic carbonates from CO2 and epoxides. References: 1 Q. He, J. W. O’Brien, K. a. Kitselman, L. E. Tompkins, G. C. T. Curtis and F. M. Kerton, Catal. Sci. Technol., 2014, 4, 1513. 2 T. J. Collins, Acc. Chem. Res., 2002, 35, 782–790. 3 M. Adolph, T. a Zevaco, C. Altesleben, O. Walter and E. Dinjus, Dalton Trans., 2014, 43, 3285–96.