Fe-Mediated S–S Bond Cleavage and Its Application in the Synthesis of α-Arylthio Carbonyl Compounds

Abstract

In the presence of iron dust, diaryl disulfides react with α-bromo carbonyl compounds to obtain α-arylthio carbonyl compounds in good yield at 90 °C under an N₂ atmosphere, using commercial dimethylformamide (DMF) as solvent. The possible reaction mechanism is that the disulfide is reduced by iron dust to give ArSFeSAr and then reacted with α-bromo carbonyl compounds to give product α-arylthio carbonyl compounds and FeBr₂.

GRAPHICAL ABSTRACT

Keywords:

• α-Bromo carbonyl compounds
• diaryl disulfides
• iron dust

SUPPLEMENTAL MATERIAL

All compounds are known from the literature, and full experimental details and ¹H NMR and ¹³C NMR data for this article can be accessed on the publisher’s website.