Fullerene soot and a fullerene nanodispersion as recyclable heterogeneous off-the-shelf photocatalysts

Metal-free heterogeneous photocatalysis, which requires no prior catalyst immobilization or chemical modification and can operate in green solvents, represents a highly-sought after, yet currently still underdeveloped, synthetic method. In this report we present a comparative study which aims to evaluate the use of unmodified fullerene soot and a fullerene nanodispersion as non-soluble and quasi-soluble carbon-based photocatalysts, respectively, for sulfide oxidation and other transformations using oxygen as an oxidant in ethanol. A wide range of sulfoxides were successfully prepared with good yields and chemoselectivity using a very low catalyst loading. The fullerene soot photocatalyst is easily recovered and shows excellent stability of the catalytic properties. The reaction was shown to proceed via a singlet oxygen pathway and has a high selectivity for aliphatic sulfides, whereas the oxidation of thioanisoles can be accomplished using an amine mediated electron transfer mechanism. The applicability of the fullerene nanodispersion as a general purpose photocatalyst was demonstrated in radical cyclization, boronic acid oxidation and imine formation reactions.

Automated summary

Metal-free heterogeneous photocatalysis using unmodified fullerene soot and fullerene nanodispersion as carbon-based photocatalysts have shown high efficiency and selectivity in sulfide oxidation reactions in ethanol. The fullerene soot photocatalyst is easily recoverable and demonstrates stable catalytic properties. Additionally, the fullerene nanodispersion has shown potential as a general purpose photocatalyst in various other reactions.