Selective C-H Acyloxylation of Sulfides/Disulfides Enabled by Hypervalent Iodine Reagents

Herein, we report the alpha-C-H acyloxylation of sulfides and disulfides enabled by hypervalent iodine(III) reagents via photoredox catalysis. The methoxylbenziodoxole derivatives serve as the hydrogen atom transfer agent, the mild oxidant, and the acyloxylation source in the reaction. External nucleophiles can also be introduced to the alpha-C-H of sulfides. The reaction applies to various aryl and alkyl sulfides including methionine peptide derivatives. Disulfides are applicable for the first time with excellent chemoselectivity and functional group compatibility.

Automated summary

In this study, we demonstrate the alpha-C-H acyloxylation of sulfides and disulfides using hypervalent iodine(III) reagents and photoredox catalysis. Methoxylbenziodoxole derivatives act as hydrogen atom transfer agents, mild oxidants, and acyloxylation sources in the reaction. External nucleophiles can also be introduced to the alpha-C-H of sulfides. This reaction is applicable to various aryl and alkyl sulfides, including methionine peptide derivatives. Disulfides can be used for the first time with excellent chemoselectivity and functional group compatibility.