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Synthesis 2008(15): 2417-2426  
DOI: 10.1055/s-2008-1067127
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Free Copper-Catalyzed Sonogashira Cross-Coupling at Room Temperature

Huimin Jianga,b, Hua Fu*a, Renzhong Qiao*b, Yuyang Jiang*a,c, Yufen Zhao*a
a Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: fuhua@mail.tsinghua.edu.cn;
b Department of Pharmaceutical Engineering, College of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, P. R. of China
e-Mail: qiaorz@mail.buct.edu.cn;
c Key Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. of China
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Publication History

Received 18 March 2008
Publication Date:
11 June 2008 (online)

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Abstract

We have developed an efficient method for the palladium-free copper-catalyzed Sonogashira cross-coupling of o-iodo­acetanilide derivatives with alkynes at room temperature; the corresponding coupling products were obtained in good to excellent yields using copper(I) iodide/N-methylpyrrolidine-2-carboxamide as the catalyst. This inexpensive catalyst system has high tolerance towards various functional groups in the substrates. This represents the lowest reaction temperatures for copper-catalyzed Sonogashira cross-coupling thus far.

Key words

Sonogashira reaction - cross-coupling - copper catalysis - N,N-ligand - room temperature