A new approach to benzofuran synthesis: Lewis acid mediated cycloaddition of benzoquinones with stilbene oxides

We report a BF(3)-mediated novel dehydrative cycloaddition reaction of benzoquinones with stilbene oxides to afford 2,3-diaryl-5-hydroxybenzofurans and 2,3-diai-yl-5-hydroxydihydrobenzofurans in good combined yields. No change in the products or the yield is observed when using diphenylacetaldehyde and cis-stilbene oxide instead of trans-stilbene oxides. When stilbene oxide is reacted with hydroquinone instead of the corresponding benzoquinone under the same conditions, dihydrobenzofuran is isolated in high yield. On the basis of these results, we propose the following possible reaction mechanism: stilbene oxide is converted to a phenonium ion (the key intermediate), which undergoes nucleophilic attack by benzoquinone or the simultaneously generated hydroquinone and subsequent dehydrative intramolecular cyclization to afford benzofuran or dihydrobenzofuran, respectively. (C) 2009 Elsevier Ltd. All rights reserved.