Lewis acid-catalyzed, copper(II)-mediated synthesis of heteroaryl thioethers under base-free conditions

J Org Chem. 2012 May 4;77(9):4414-9. doi: 10.1021/jo202624s. Epub 2012 Apr 17.

Abstract

A Lewis acid (Ag(I), Ni(II), or Fe(II)) catalyzed, Cu(II)-mediated thiolation reaction between heteroarenes and thiols was achieved with good yield under base-free conditions. DMSO could serve as an effective methylthiolation reagent for the synthesis of heterocyclic methyl thioethers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Lewis Acids / chemistry*
  • Metals / chemistry*
  • Molecular Structure
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry

Substances

  • Heterocyclic Compounds
  • Lewis Acids
  • Metals
  • Sulfides
  • Copper