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Mild and Highly Selective Palladium-Catalyzed Monoarylation of Ammonia Enabled by the Use of Bulky Biarylphosphine Ligands and Palladacycle Precatalysts

Chi Wai Cheung, David S. Surry and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

C. W. Cheung, D. S. Surry, S. L. Buchwald, Org. Lett., 2013, 15, 3734-3737.

DOI: 10.1021/ol401612c (free Supporting Information)


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Abstract

In a Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, excellent selectivity for monoarylation was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands as well as their corresponding aminobiphenyl palladacycle precatalysts. As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.

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Key Words

Arylation


ID: J54-Y2013