N-Heterocyclic carbene-catalyzed formal cross-coupling reaction of α-haloenals with thiols: organocatalytic construction of sp2 carbon-sulfur bonds

Chem Commun (Camb). 2014 Apr 11;50(28):3719-21. doi: 10.1039/c4cc00154k.

Abstract

A novel N-heterocyclic carbene (NHC)-catalyzed formal cross-coupling reaction between α-haloenals and thiols was developed. In the presence of 5 mol% NHC precursors and 1.6 equiv. potassium carbonate, various thiols coupled with α-haloenals to produce α-thioenals in 53% to 91% yield and excellent Z-selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Sulfhydryl Compounds / chemistry*
  • Sulfur / chemistry

Substances

  • Heterocyclic Compounds
  • Sulfhydryl Compounds
  • carbene
  • Sulfur
  • Carbon
  • Methane