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
Current Organic Chemistry
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.
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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
DOI https://dx.doi.org/10.2174/138527212804004490 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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