Isolation of a C5-deprotonated imidazolium, a crystalline "abnormal" N-heterocyclic carbene

Science. 2009 Oct 23;326(5952):556-9. doi: 10.1126/science.1178206.

Abstract

The discovery two decades ago of metal-free stable carbenes, especially imidazol-2-ylidenes [N-heterocyclic carbenes (NHCs)], has led to numerous breakthroughs in organic and organometallic catalysis. More recently, a small range of complexes has been prepared in which alternative NHC isomers, namely imidazol-5-ylidenes (also termed abnormal NHCs or aNHCs, because the carbene center is no longer located between the two nitrogens), coordinate to a transition metal. Here we report the synthesis of a metal-free aNHC that is stable at room temperature, both in the solid state and in solution. Calculations show that the aNHC is more basic than its normal NHC isomer. Because the substituent at the carbon next to the carbene center is a nonbulky phenyl group, a variety of substitution patterns should be tolerated without precluding the isolation of the corresponding aNHC.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemical Phenomena
  • Crystallization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / isolation & purification*
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / isolation & purification*
  • Isomerism
  • Molecular Structure
  • Protons
  • Temperature
  • Thermodynamics

Substances

  • Heterocyclic Compounds
  • Imidazoles
  • Protons