Oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran with molecular oxygen in the presence of N-hydroxyphthalimide

• NHPI/Cu(NO3)2 shows superior catalytic activity in the HMF aerobic oxidation.
• The main oxidation product is 2,5-diformylfuran.
• Oxidation takes place in mild conditions.
• The plausible mechanism of the catalysis is proposed.

Catalytic system Cu(NO3)2/NHPI can be successfully used for the mild oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran with molecular oxygen. The oxidation reaction takes place at 50 °C and 1 atm O2 and selectively converts the primary hydroxymethyl group of HMF to the aldehyde one. The selective formation of aromatic aldehyde is observed because of the higher rate of hydrogen abstraction from primary alcohols by the phthalimide-N-oxyl radical, as compared to the rate of the hydrogen abstraction from the aldehydes.

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