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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.more » « less
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Dorn, Rick W.; Paterson, Alexander L.; Hung, Ivan; Gor’kov, Peter L.; Thompson, Austin J.; Sadow, Aaron D.; Gan, Zhehong; Rossini, Aaron J. (, The Journal of Physical Chemistry C)
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Basemann, Kevin; Schmidt, Bradley M.; Sadow, Aaron D. (, ACS Catalysis)
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Kanbur, Uddhav; Sadow, Aaron D. (, Chemistry – A European Journal)
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