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
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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