Metal-Free Tandem Friedel-Crafts/Lactonization Reaction to Benzofuranones Bearing a Quaternary Center at C3 Position

Long Chen, Feng Zhou, Tao-Da Shi and Jian Zhou*

*Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P. R. China, Email: jzhouchem.ecnu.edu.cn

L. Chen, F. Zhou, T.-D. Shi, J. Zhou, J. Org. Chem., 2012, 77, 4354-4362.

DOI: 10.1021/jo300395x

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Abstract

A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones is catalyzed by HClO₄. The reaction of various tertiary α-hydroxy acid esters with substituted phenols affords the desired products in rich diversity. ¹H NMR studies supports that this tandem reaction proceeds via tandem Friedel-Crafts/lactonization sequence.

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Key Words

Lactones, Friedel-Crafts Alkylation, benzofuranones

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ID: J42-Y2012-1280