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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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 and Thomas Rosenau

Volume 16, Issue 22, 2012

Page: [2739 - 2744] Pages: 6

DOI: 10.2174/138527212804004490

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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