Continuous Bioinspired Oxidation of Sulfides

Molecules. 2020 Jun 11;25(11):2711. doi: 10.3390/molecules25112711.

Abstract

A simple, efficient, and selective oxidation under flow conditions of sulfides into their corresponding sulfoxides and sulfones is reported herein, using as a catalyst perselenic acid generated in situ by the oxidation of selenium (IV) oxide in a diluted aqueous solution of hydrogen peroxide as the final oxidant. The scope of the proposed methodology was investigated using aryl alkyl sulfides, aryl vinyl sulfides, and dialkyl sulfides as substrates, evidencing, in general, a good applicability. The scaled-up synthesis of (methylsulfonyl)benzene was also demonstrated, leading to its gram-scale preparation.

Keywords: catalysis; flow chemistry; hydrogen peroxide; oxidation; selenium dioxide; sulfide; sulfone; sulfoxide.

MeSH terms

  • Catalysis
  • Hydrogen Peroxide / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Selenium Oxides / chemistry
  • Sulfides / chemistry*
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry
  • Sulfoxides / chemical synthesis*
  • Sulfoxides / chemistry

Substances

  • Selenium Oxides
  • Sulfides
  • Sulfones
  • Sulfoxides
  • Hydrogen Peroxide