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Synfacts 2010(10): 1190-1190  
DOI: 10.1055/s-0030-1258676
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

DMEDA-Catalyzed Cross-Coupling of Unactivated Benzene

Contributor(s): Benjamin List, Anna Lee
W. Liu, H. Cao, H. Zhang, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y. Kwong*, A. Lei*
The Hong Kong Polytechnic University, Wuhan University and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication Date:
22 September 2010 (online)

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Significance

A novel concept for the cross-­coupling of benzene using the N,N′-dimethyl­ethane-1,2-diamine (DMEDA) catalyst in the ­presence of potassium tert-butoxide (KOt-Bu) is reported. The authors carefully checked the possibility of the presence of trace transition-metal elements in the commercially available KOt-Bu, but similar results were obtained after repurification of the base. In the presence of radical scavengers, such as TEMPO and diyldibenzene, the reactions did not take place. Also, a low conversion was observed after adding a stoichiometric amount of 18-crown-6 to trap the potassium ion. The authors suggest that the mechanism of this reaction would involve an aryl radical anion as an intermediate.