Synthesis of substituted thiophenes by palladium-catalyzed heterocyclodehydration of 1-mercapto-3-yn-2-ols in conventional and nonconventional solvents

J Org Chem. 2012 Nov 2;77(21):9905-9. doi: 10.1021/jo301943k. Epub 2012 Oct 15.

Abstract

A variety of readily available 1-mercapto-3-yn-2-ols 5 were conveniently converted into the corresponding thiophenes 6 in good to high yields in MeOH as the solvent at 50-100 °C in the presence of catalytic amounts (1-2%) of PdI(2) in conjunction with KI (KI:PdI(2) molar ratio = 10). The catalyst could be made recyclable employing an ionic liquid, such as BmimBF(4), as the solvent under suitable conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Ionic Liquids
  • Molecular Structure
  • Palladium / chemistry*
  • Solvents / chemistry*
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry*

Substances

  • Heterocyclic Compounds
  • Ionic Liquids
  • Solvents
  • Thiophenes
  • Palladium