Polysiloxane-supported fullerene derivative as a new heterogeneous sensitiser for the selective photooxidation of sulfides to sulfoxides by 1O2

A heterogeneous photosensitiser for the generation of singlet oxygen was synthesized by covalent attachment of a methanofullerene derivative to polysiloxane-based Deloxan® DAP beads and its performance in the photooxidation of sulfides to sulfoxides was investigated. As opposed to C60 and many of its derivatives, the heterogeneous sensitiser can be readily used in protic solvents such as methanol which makes the photooxygenation highly selective, affording good to excellent yields of sulfoxides with aliphatic and benzylic sulfides. Moreover, the sensitiser is easily recovered at the end of the reaction by simple filtration.