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Synthesis 2010(3): 515-519  
DOI: 10.1055/s-0029-1217129
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Two-Step Synthesis of 2-Arylbenzofurans

Xin-Fang Duan*, Jian-Xia Feng, Zhan-Bin Zhang
Department of Chemistry, Beijing Normal University, Beijing, 100875, P. R. of China
Fax: +86(10)58802075; e-Mail: xinfangduan@vip.163.com;
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Publication History

Received 15 September 2009
Publication Date:
20 November 2009 (online)

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Abstract

A novel and convenient two-step synthesis of 2-arylbenzofurans is described which proceeds via a selective cross-pinacol-type coupling between a salicylaldehyde and an aromatic aldehyde, followed by an acid-promoted cyclization. One advantage of this method is that separation of the three possible pinacol products that can form during the cross-coupling is not necessary. This method is also applied to the synthesis of the 2-arylbenzofuran-containing natural product, homoegonol.

Key words

pinacols - pinacol-type coupling - cross-coupling - benzofurans - 2-arylbenzofurans

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12

In several of the reactions, a small amount of alkenes formed as byproducts during the cross-coupling which hindered the acid-promoted cyclization of the pinacol products. Although it was not necessary to separate the three pinacols, the alkene by-product was removed by chromatography.