Synthesis 2010(8): 1280-1284  
DOI: 10.1055/s-0029-1218661
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

3-Acetylcoumarin as a Practical Ligand for Copper-Catalyzed C-N Coupling Reactions at Room Temperature

Chuan-Zhou Tao*a,b, Wei-Wei Liua, Ji-You Suna, Zhi-Ling Caoa, Hui Lia, Ying-Fen Zhanga
a Department of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, P. R. of China
b Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology, Lianyungang 222005, P. R. of China
Fax: +86(518)85895403; e-Mail: cztao@mail.ustc.edu.cn;
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Publikationsverlauf

Received 27 October 2009
Publikationsdatum:
05. Februar 2010 (online)

Abstract

The use of coumarin-based ligands was examined in copper-catalyzed C-N cross-coupling reactions. It was found that 3-acetylcoumarin constituted a new, practical ligand for the copper-catalyzed N-arylation of aliphatic amines and imidazole with aryl iodides at room temperature. Aryl bromides could also be aminated efficiently at 80 ˚C. This readily available catalyst system, namely copper(I) iodide and 3-acetylcoumarin, provides a mild and practical method for the synthesis of aromatic amines.