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Synthesis 2010(19): 3289-3294  
DOI: 10.1055/s-0030-1257937
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Room-Temperature, Copper-Catalyzed Cascade Process for Diethyl 2-Aryl-3,4-dihydro-4-oxo-1,1(2H)-naphthalenedicarboxylate

Zhengqiu Lia,b, Liangbin Fub,c, Jiajia Weic, Chengyong Haa, Duanqing Peic, Qian Cai*c, Ke Ding*c
a Key Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. of China
b Graduate School of the Chinese Academy of Sciences, Beijing, P. R. of China
c Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No.190, Kaiyuan Avenue, Science Park, Guangzhou 510530, P. R. of China
Fax: +86(20)32015299; e-Mail: cai_qian@gibh.ac.cn; e-Mail: ding_ke@gibh.ac.cn;
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Publication History

Received 23 March 2010
Publication Date:
30 July 2010 (online)

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Abstract

A room-temperature cascade process for the formation of diethyl 2-aryl-3,4-dihydro-4-oxo-1,1(2H)-naphthalenedicarboxylate is described by using a combination of Michael addition and copper-catalyzed α-arylation of malonic acid derivatives. The protocol worked well for a variety of 1-(2-iodoaryl)enones and displayed great functional group compatibility.

Key words

Michael addition - copper - catalysis - cascade reactions - α-arylation