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Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts

Rebecca A. Green and John F. Hartwig*

*Department of Chemistry, University of California, Berkeley, California 94720, United States, Email: jhartwigberkeley.edu

R. A. Green, J. F. Hartwig, Org. Lett., 2014, 16, 4388-4391.

DOI: 10.1021/ol501739g  (free Supporting Information)



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Abstract

A palladium-catalyzed coupling of aryl chlorides with ammonia and gaseous amines as their ammonium salts provides monoarylated products with high selectivity. The resting state for reactions of aryl chlorides is different from the resting state for reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes.

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Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines

G. D. Vo, J. F. Hartwig, J. Am. Chem. Soc., 2009, 131, 11049-11061.


Key Words

anilines, Buchwald-Hartwig Coupling


ID: J54-Y2014