Mild and Highly Selective Palladium-Catalyzed Monoarylation of Ammonia Enabled by the Use of Bulky Biarylphosphine Ligands and Palladacycle Precatalysts
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Buchwald_Mild and highly.pdf
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Author(s)
Cheung, Chi Wai
Surry, David S.
Buchwald, Stephen Leffler
Date Issued
July 2013
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Cheung, Chi Wai, David S. Surry, and Stephen L. Buchwald. “Mild and Highly Selective Palladium-Catalyzed Monoarylation of Ammonia Enabled by the Use of Bulky Biarylphosphine Ligands and Palladacycle Precatalysts.” Org. Lett. 15, no. 14 (July 19, 2013): 3734–3737.
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Author's final manuscript
Abstract
A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ol401612c
