New Family of N-Heterocyclic Carbenes for Organocatalysis

  • Author: ChemViews
  • Published Date: 26 August 2011
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: New Family of N-Heterocyclic Carbenes for Organocatalysis

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N-Heterocyclic carbene (NHC) organocatalysis has attracted considerable attention due to facile reaction handling, environmental friendliness, and low cost and toxicity compared with transition-metal catalysts. In each NHC-catalyzed transformation, the proper choice of NHC is crucial for success; the development of structurally related families of NHCs with slightly different properties is, therefore, of great interest.

Frank Glorius and colleagues, Westfälische Wilhelms-University, Münster, Germany, have synthesized a family of thiazolylidenes-based NHCs. The NHCs are based on a N-mesityl-substituted thiazolylidene with a cycloheptane backbone. The backbone architecture was varied by employing different arylamines and α-bromo ketones in a two-step synthesis. The NHCs are effective organocatalysts for promoting the chemoselective intermolecular cross-benzoin condensation leading to unsymmetrically substituted benzoins and may be applicable to other organocatalytic processes.

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