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.

Forchetta, M., Sabuzi, F., Stella, L., Conte, V., Galloni, P. (2022). KuQuinone as a highly stable and reusable organic photocatalyst in selective oxidation of thioethers to sulfoxides. JOURNAL OF ORGANIC CHEMISTRY, 87(21), 14016-14025 [10.1021/acs.joc.2c01648].

KuQuinone as a highly stable and reusable organic photocatalyst in selective oxidation of thioethers to sulfoxides

Sabuzi F.;Stella L.;Conte V.;Galloni P.
2022-01-01

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.
2022
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/06 - CHIMICA ORGANICA
English
Con Impact Factor ISI
Forchetta, M., Sabuzi, F., Stella, L., Conte, V., Galloni, P. (2022). KuQuinone as a highly stable and reusable organic photocatalyst in selective oxidation of thioethers to sulfoxides. JOURNAL OF ORGANIC CHEMISTRY, 87(21), 14016-14025 [10.1021/acs.joc.2c01648].
Forchetta, M; Sabuzi, F; Stella, L; Conte, V; Galloni, P
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/308696
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