Graphite oxide: a selective and highly efficient oxidant of thiols and sulfides

Org Biomol Chem. 2011 Nov 7;9(21):7292-5. doi: 10.1039/c1ob06102j. Epub 2011 Sep 12.

Abstract

The selective oxidation of thiols to disulfides and sulfides to sulfoxides using graphite oxide (GO), a heterogeneous carbocatalyst obtained from low cost, commercial starting materials is described. The aforementioned oxidation reactions were found to proceed rapidly (as short as 10 min in some cases) and in good yield (51-100%) (19 examples). No over-oxidation of the substrates was observed, and GO's heterogeneous nature facilitated isolation and purification of the target products.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Graphite / chemistry*
  • Molecular Structure
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Oxides / chemistry*
  • Stereoisomerism
  • Substrate Specificity
  • Sulfhydryl Compounds / chemistry*
  • Sulfides / chemical synthesis
  • Sulfides / chemistry*
  • Sulfoxides / chemical synthesis
  • Sulfoxides / chemistry

Substances

  • Oxidants
  • Oxides
  • Sulfhydryl Compounds
  • Sulfides
  • Sulfoxides
  • Graphite