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

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

Volume: 16 Issue: 22

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

Affiliation:

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

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.

Cite this article as:

Opietnik Martina, Jungbauer Alois, Mereiter Kurt and Rosenau Thomas, Mild Friedel-Crafts Acylation of Furan with Carboxylic Acids and the Heterogeneous Catalyst Couple AlPW12O40 / Mg(OH)2, Current Organic Chemistry 2012; 16 (22) . https://dx.doi.org/10.2174/138527212804004490