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Copper-Diamine-Catalyzed N-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles

Jon C. Antilla, Jeremy M. Baskin, Timothy E. Barder and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

J. C. Antilla, J. M. Baskin, T. E. Barder, S. L. Buchwald, J. Org. Chem., 2004, 69, 5578-5587.

DOI: 10.1021/jo049658b (free Supporting Information)


Abstract

N-arylation of either aryl iodides or aryl bromides with common π-excessive nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate various functional groups and hindered substrates.

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4,7-Dimethoxy-1,10-phenanthroline: An Excellent Ligand for the Cu-Catalyzed N-Arylation of Imidazoles

R. A. Altman, S. L. Buchwald, Org. Lett., 2006, 8, 2779-2782.


Key Words

Ullmann Synthesis, N-Arylation


ID: J42-Y2004-620