KuQuinone as a Highly Stable and Reusable Organic Photocatalyst in Selective Oxidation of Thioethers to Sulfoxides was written by Forchetta, Mattia;Sabuzi, Federica;Stella, Lorenzo;Conte, Valeria;Galloni, Pierluca. And the article was included in Journal of Organic Chemistry in 2022.Synthetic Route of C7H9NS This article mentions the following:
A chemoselective photocatalytic system to perform oxidation of thioethers to sulfoxides RS(O)R1 [R = nBu, Ph, Bn, etc.; R1 = Me, Ph, Bn, etc.] was presented. The light-induced oxidation process was 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 Me Ph sulfoxide in 60 min. Remarkably, the system could be recharged and recycled without a loss of activity and selectivity, reached to turnover numbers (TONs) higher than 4000. Excellent catalytic performances and full selectivity was also been obtained for the photocatalytic oxidation of substituted thioanisole derivatives, aliphatic, cyclic and diaryl thioethers. Likewise, the oxidation of heteroaromatic organosulfur compounds could be accomplished with longer reaction times. In the experiment, the researchers used many compounds, for example, 4-(Methylthio)aniline (cas: 104-96-1Synthetic Route of C7H9NS).
4-(Methylthio)aniline (cas: 104-96-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Synthetic Route of C7H9NS
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica