Copper(I) iodide catalyzed redistribution of aromatic carboxylic acids
Journal of Catalysis(2024)
摘要
Copper(I) iodide catalyzes the disproportionation of aromatic and heteroaromatic carboxylic acids to give dicarboxylic acids. Potassium furoate heated to 280 – 300 °C in the presence of 10 mol % CuI under carbon dioxide (40 bar) forms dipotassium 2,5-furandicarboxylate (2,5-FDCK), which is isolated as pure 2,5-dicarboxylic acid (2,5-FDCA) in up to 75 % isolated yield and in excellent selectivity over the regioisomeric 2,4-furandicarboxylate (92 % selectivity). Starting materials are recovered in experiments lacking CuI or with pressurized N2 replacing CO2, whereas high conversion and low yields of 2,5-FDCA are obtained with moderate CO2 pressures, suggesting several roles for carbon dioxide in the transformation. Similarly, potassium benzoate heated to 320 – 350 °C in the presence of 10 mol % CuI under carbon dioxide (40 bar) produces terephthalic acid after workup in up to 60 % yield.
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关键词
Furandicarboxylic acid,Terephthalic acid,Henkel reaction,Earth-abundant catalyst,Copper iodide
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