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