New Carbene Chemistry

  • Author: ChemistryViews
  • Published: 26 October 2010
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Chemical Sciences/RSC
thumbnail image: New Carbene Chemistry

Ulrich Siemeling and colleagues, University of Kassel, Germany, have shown that stable N-heterocyclic carbenes (NHCs) can show strongly enhanced reactivities towards fundamentally important small molecules such as ammonia and carbon monoxide, which is unprecedented for diaminocarbene compounds.

The scientists demonstrate that a ferrocene-based NHC is able to add ammonia, methyl acrylate, tert-butyl isocyanide, and carbon monoxide—reactions typical of (alkyl)(amino)carbenes, but unprecedented for diaminocarbenes. They also show that even the simplest stable diaminocarbene, C(NiPr2)2, adds CO. This reaction provideds a new entry to the important β-lactam ring systems commonly found in antibiotics.

The newly discovered reactivity of diaminocarbenes opens the door to an exciting area of synthetically useful carbene chemistry.

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