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Synfacts 2009(8): 0893-0893  
DOI: 10.1055/s-0029-1217485
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I)-Catalyzed Amination of Aryl Halides with Aqueous Ammonia

Contributor(s):Paul Knochel, Andrei Gavryushin
H. Xu, C. Wolf*
Georgetown University, Washington, USA
Efficient Copper-Catalyzed Coupling of Aryl Chlorides, Bromides and Iodides with Aqueous Ammonia
Chem. Commun.  2009,  3035-3037  
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Publication History

Publication Date:
23 July 2009 (online)

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Key words

amination - aryl halides - copper

Significance

This new amination method has many advantages: It is operationally simple, utilizes aqueous ammonia which is easy to handle and inexpensive Cu2O as a catalyst. It can be applied to aryl iodides, bromides and chlorides and tolerates a broad range of functionalities. It is highly selective and primary anilines are obtained chemoselectively, thus, without the formation of di- and triarylamines.

Comment

Noticeably, aryl chlorides react only under microwave irradiation conditions, otherwise no product forms even at 160 ˚C. Under basic anhydrous conditions (LiNH2, dioxane), copper(I) ­oxide leads exclusively to the formation of triaryl-amines. Recently, a copper(II)-NHC catalyst was developed for a similar amination protocol (N. Xia, M. Taillefer Angew. Chem. Int. Ed. 2009, 48, 337).

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