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

doi:10.1055/s-0029-1217485

Synfacts 2009(8): 0893-0893
DOI: 10.1055/s-0029-1217485

Metal-Mediated Synthesis

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

Rezensent(en):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

Abstract

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Key words

amination - aryl halides - copper

Significance

<P>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.</P>

Comment

<P>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).</P>

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