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Synthesis 2009(7): 1075-1080  
DOI: 10.1055/s-0028-1083356
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of 1,4-Diarylnaphthalenes via a Wittig-Horner Reaction/[4+2] Cycloaddition/Dehydrogenation Sequence

Zhengbo Chen, Wangge Shou, Yanguang Wang*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87951512; e-Mail: orgwyg@zju.edu.cn;
Further Information

Publication History

Received 14 October 2008
Publication Date:
11 February 2009 (online)

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Abstract

A one-pot synthesis of 1,4-diarylnaphthalenes from cinnamaldehydes, dimethyl benzylphosphonates, and benzenediazonium-2-carboxylate is described. The tandem process involves the Wittig-Horner reaction of the cinnamaldehyde with the benzylphosphonate, [4+2] cycloaddition of the thus-formed diene with benzyne, and subsequent dehydrogenation. The procedure is general and efficient and the substrates are readily available.

Key words

diphenylnaphthalene - tandem reaction - Wittig-Horner reaction - cycloaddition - benzyne

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