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Copper-Catalyzed N-Arylation of Imidazoles and Benzimidazoles

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Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
Cite this: J. Org. Chem. 2007, 72, 16, 6190–6199
Publication Date (Web):July 11, 2007
Copyright © 2007 American Chemical Society

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    Abstract Image

    4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.


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