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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
KuQuinone as a Highly Stable and Reusable Organic Photocatalyst in Selective Oxidation of Thioethers to Sulfoxides
Mattia Forchetta1, Federica Sabuzi1, Lorenzo Stella1
1Department of Chemical Science and Technologies, University of Rome Tor Vergata, Via della Ricerca Scientifica, 00133 Rome, Italy.
Abstract:
A chemoselective photocatalytic system to perform thioether oxidation to sulfoxide is presented. The light-induced oxidation process is here promoted by a metal-free quinoid catalyst, namely 1-hexylKuQuinone (KuQ). Reactions performed in a fluorinated solvent (i.e., HFIP), using O2 as the oxidant, at room temperature, lead to complete thioanisole conversion to methyl phenyl sulfoxide in 60 min. Remarkably, the system can be recharged and recycled without a loss of activity and selectivity, reaching turnover numbers (TONs) higher than 4000. Excellent catalytic performances and full selectivity have also been obtained for the photocatalytic oxidation of substituted thioanisole derivatives, aliphatic, cyclic, and diaryl thioethers. Likewise, the oxidation of heteroaromatic organosulfur compounds can be accomplished, with longer reaction times.
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