Mild Friedel-Crafts Acylation of Furan with Carboxylic Acids and the Heterogeneous Catalyst Couple AlPW12O40 / Mg(OH)2

Author(s): Martina Opietnik , Alois Jungbauer , Kurt Mereiter , Thomas Rosenau .

Journal Name: Current Organic Chemistry

Volume 16 , Issue 22 , 2012

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Abstract:

Many bioactive compounds contain 2-furanoyl moieties. Classical Friedel-Crafts acylation conditions fail completely in the case of the sensitive and polymerization-prone furan, or give only rather unsatisfying yields only. The heterogeneous catalyst couple consisting of equimolar amounts of the stable and non-hygroscopic heteropolyacid aluminum dodecatungstophosphate (AlPW12O40)1 in combination with Mg(OH)2 was used for the direct reaction between furan and a variety of free carboxylic acids to regioselectively produce 2-furyl-alkylketones and 2-furyl-arylketones in good to excellent yields. The approach worked even in cases of labile benzofuran and indole derivatives where all alternative approaches failed.

Keywords: Friedel-Crafts-type acylation, AlPW12O40, 2-furylketones, furan, green chemistry

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Article Details

VOLUME: 16
ISSUE: 22
Year: 2012
Page: [2739 - 2744]
Pages: 6
DOI: 10.2174/138527212804004490

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