Synthetic Approaches to Sterically Hindered N‐Arylimidazoles through Copper‐Catalyzed Coupling Reactions
- 1 April 2005
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2005 (8), 1637-1643
- https://doi.org/10.1002/ejoc.200400453
Abstract
Optimization studies allowed the efficient synthesis of a simple structural motif based on meta-bis(1-imidazolyl)benzenes 1 through copper-catalyzed coupling of 1,3-diiodobenzene and imidazole under mild reaction conditions. This protocol was then used to prepare a representative sterically hindered N-arylimidazole 2a, the most common structural motif among N-heterocyclic carbenes (NHC). Having optimized the main variables governing CuI-catalyzed imidazole N-arylation, the first Ullmann-type synthesis of N-mesitylimidazole (2a) is reported. Moreover, the coupling between boronic acids as the aryl donor partners and either imidazole or benzimidazole was examined; in all cases the reactions proceeded in very low yield. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)Keywords
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