(PhCH₂PPh₃)⁺Br₃⁻: A Versatile Reagent for the Chemoselective Oxidation of Sulfides to Sulfoxides

Abstract

Benzyltriphenylphosphonium tribromide (BTPTB), as a stable solid reagent, is easily prepared by the reaction of benzyltriphenylphosphonium bromide with Br₂. This reagent can be used as an efficient reagent for the chemoselective oxidation of dialkyl and aryl-alkyl sulfides to their corresponding sulfoxides in the presence of diaryl sulfides and primary alcohols. All reactions were performed in a refluxing mixture of methanol and water in very short reaction times.

Keywords:

• Benzyltriphenylphosphonium bromide
• benzyltriphenylphosphonium tribromide
• chemoselective oxidation
• sulfides
• sulfoxides

Acknowledgments

We are thankful to the University of Guilan and Mohaghegh-Ardabili University Research Councils for the partial support of this work.

Notes

^a Products were characterized by their physical data, comparison with authentic samples, and IR and NMR spectroscopy.

^b Isolated yield.

^c Conversion.