Oxygen is a near-ideal oxidant, but it is underutilized in pharmaceutical and fine chemical industries due to safety concerns and a lack of suitable synthetically useful reactions. We have developed an efficient aerobic alcohol oxidation protocol that uses a CuI(OTf)/bpy/TEMPO/N-methylimidazole catalyst system that mediates highly selective oxidation of primary alcohols to aldehydes.  This method has been adapted to operate under flow conditions, and it exhibits improved performance under higher pressure and elevated temperatures. The catalyst rapidly oxidizes benzylic and more demanding aliphatic alcohols with residence times as short as five minutes. The oxidation of benzyl alcohol was scaled up to 100 g with reduced catalyst loading and the reaction exhibits significantly improved process mass intensity relative to a similar, recently reported process that employs a palladium(II) catalyst system (Ye et al. Green Chem.2010 , 12, 1180-1186).

Continuous flow method for selective aerobic alcohol oxidation of primary alcohols to aldehydes

246th National Meeting (2013)

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