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Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation

Takashi Ikawa, Timothy E. Barder, Mark R. Biscoe and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, Email:

T. Ikawa, T. E. Barder, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc., 2007, 129, 13001-13007.

DOI: 10.1021/ja0717414


The use of monodentate ligands that possess a methyl group ortho to the phosphorus center allows the coupling of various aryl and heteroaryl chlorides with various amides in high yield. These ligands can prevent the formation of the κ2-amidate complexes and thereby generate more stable catalysts for the amination of aryl chlorides.

see article for more examples

Pd-Catalyzed Cross-Coupling Reactions of Amides and Aryl Mesylates

K. Dooleweerdt, B. P. Fors, S. L. Buchwald, Org. Lett., 2010, 12, 2350-2353.

Pd-Catalyzed Intermolecular Amidation of Aryl Halides: The Discovery that Xantphos Can Be Trans-Chelating in a Palladium Complex

J. Yin, S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.

Key Words


ID: J48-Y2007-3510