Synthetic Approaches to Sterically Hindered N-Arylimidazoles through Copper-Catalyzed Coupling Reactions

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...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2005-04, Vol.2005 (8), p.1637-1643
Main Authors: Alcalde, Ermitas, Dinarès, Immaculada, Rodríguez, Sandra, Garcia de Miguel, Cristina
Format: Article
Language:English
Subjects:
Arylation
Benzimidazole
Imidazole
N-Heterocyclic carbenes
Ullman-type condensation
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Summary: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400453