Abstract
In this work, we developed a nickel-catalyzed transfer hydrogenolysis of 1-aryloxy-3-amino-2-propanols, which is a model compound of an amine-cured bisphenol A (BPA)-based epoxy resin. Mechanistic investigation revealed that the hydroxy group acts as the hydrogen donor to generate α-aryloxy ketone, which undergoes an unprecedented remote-concerted oxidative addition of the C(sp3)-O bond as suggested by DFT calculation. Successful application of this method was demonstrated by the degradation of a diamine-cured BPA-based epoxy resin, in which BPA was directly recovered from the resin.
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