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

Giang D. Vo and John F. Hartwig*

*Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, Email: jhartwiguiuc.edu

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

DOI: 10.1021/ja903049z (free Supporting Information)

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Abstract

A complex generated from Pd[P(o-tol)₃]₂ and the alkylbisphosphine CyPF-t-Bu is a highly active and selective catalyst for the coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates. The couplings with this catalyst conducted with a solution of ammonia in dioxane form primary arylamines from various aryl electrophiles in high yields.

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[(CyPF-tBu)PdCl₂]: An Air-Stable, One-Component, Highly Efficient Catalyst for Amination of Heteroaryl and Aryl Halides

Q. Sheng, J. F. Hartwig, Org. Lett., 2008, 10, 4109-4112.

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Key Words

Buchwald-Hartwig Coupling, Anilines

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ID: J48-Y2009-2420