TEMPO functionalized C₆₀ fullerene deposited on gold surface for catalytic oxidation of selected alcohols

C₆₀TEMPO₁₀ catalytic system linked to a microspherical gold support through a covalent S-Au bond was developed. The C₆₀TEMPO₁₀@Au composite catalyst had a particle size of 0.5-0.8 μm and was covered with the fullerenes derivative of 2.3 nm diameter bearing ten nitroxyl groups; the organic film showed up to 50 nm thickness. The catalytic composite allowed for the oxidation under mild conditions of various primary and secondary alcohols to the corresponding aldehyde and ketone analogues with efficiencies as high as 79-98%, thus giving values typical for homogeneous catalysis, while retaining at the same time all the advantages of heterogeneous catalysis, e.g., easy separation by filtration from the reaction mixture. The catalytic activity of the resulting system was studied by means of high pressure liquid chromatography. A redox mechanism was proposed for the process. In the catalytic cycle of the oxidation process, the TEMPO moiety was continuously regenerated in situ with an applied primary oxidant, for example, O₂/Fe³⁺ system. The new intermediate composite components and the final catalyst were characterized by various spectroscopic methods and thermogravimetry. Graphical abstractᅟ.