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

Jinkun Huang, Gabriella Grasa and Steven P. Nolan

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

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

DOI: 10.1021/ol990987d

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Abstract

A combination of palladium and the imidazolium salt IPrHCl (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) has been used as catalyst precursor in the amination of aryl chlorides. This system proves general and efficient for aryl chlorides as well as aryl bromides and iodides.

see article for more examples

IPr

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

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

(IPr)Pd(acac)Cl: An Easily Synthesized, Efficient, and Versatile Precatalyst for C-N and C-C Bond Formation

N. Marion, E. C. Ecarnot, O. Navarro, D. Amoroso, A. Bell, S. P. Nolan, J. Org. Chem., 2006, 71, 3816-3821.

Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions

N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc., 2006, 128, 4101-4111.

Cross-Coupling and Dehalogenation Reactions Catalyzed by (N-Heterocyclic carbene)Pd(allyl)Cl Complexes

O. Navarro, H. Kaur, P. Mahjoor, S. P. Nolan, J. Org. Chem., 2004, 69, 3173-3180.

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Key Words

Buchwald-Hartwig coupling, arylamines

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ID: J54-Y1999