Copper-catalyzed thiolation of the di- or trimethoxybenzene arene C-H bond with disulfides

J Org Chem. 2010 Oct 1;75(19):6732-5. doi: 10.1021/jo1014849.

Abstract

A CuI-catalyzed direct access to sulfides from disulfides via C-H bond cleavage of di- or trimethoxybenzene is described. The procedure utilizes O(2) as a clean and cheap oxidant. Direct selenation of the C-H bond also took place under this procedure. Furthermore, the system enables the use of two RS in (RS)(2). Thus, it represents an atom-economical procedure for the synthesis of sulfides and selenides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles / chemistry*
  • Benzene Derivatives / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Disulfides / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry

Substances

  • Anisoles
  • Benzene Derivatives
  • Disulfides
  • Sulfhydryl Compounds
  • Copper
  • anisole