A Route to Gold–NHC Complexes

  • Author: ChemistryViews.org
  • Published: 14 April 2016
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Organometallics/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: A Route to Gold–NHC Complexes

N-heterocyclic carbenes (NHCs) have a wide range of applications, especially in transition-metal catalysis, due to their stability and the easy modification of their electronic and steric properties. Compared to the commonly used NHCs with five-membered rings, their six-membered counterparts have a wider N–C–N angle and higher basicity, which is interesting for catalytic applications.

A. Stephen K. Hashmi and colleagues, University of Heidelberg, Germany, have developed a synthesis strategy for such six-membered NHCs in the form of gold complexes (pictured). The team used gold isonitrile complexes and functionalized amines as building blocks, which allowed them to synthesize a wide range of six-membered NHC complexes. The reactants were combined at room temperature in the presence of the base triethylamine (NEt3) in dichloromethane (DCM) as a solvent, and the desired NHC complexes were obtained in good to excellent yields.

The method was suitable for the synthesis of unsymmetrically substituted saturated carbene complexes, but also for oxo-carbenes and partly unsaturated NHCs. These products have the potential to be functionalized further for specific applications.


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