Amination Reactions of Aryl Halides with Nitrogen-Containing Reagents Mediated by Palladium/Imidazolium Salt Systems

Gabriela A. Grasa, Mihai S. Viciu, Jinkun Huang and Steven P. Nolan*

*Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, United States, Email: steven.nolanugent.be

G. A. Grasa, M. S. Viciu, J. Huang, S. P. Nolan, J. Org. Chem., 2001, 66, 7714-7722.

DOI: 10.1021/jo010613+

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Abstract

The Pd₂(dba)₃/IPr·HCl (1, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) system offers a very high activity in amination reactions involving aryl chlorides, aryl bromides, and aryl iodides with various nitrogen-containing substrates. The ligand is also effective for the synthesis of benzophenone imines, which can be easily converted to the corresponding primary amines by acid hydrolysis.

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IPr

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General and Efficient Catalytic Amination of Aryl Chlorides Using a Palladium/Bulky Nucleophilic Carbene System

J. Huang, G. Grasa, S. P. Nolan, Org. Lett., 1999, 1, 1307-1309.

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Key Words

arylamines, anilines, Buchwald-Hartwig coupling

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ID: J42-Y2001