Nickel-Catalyzed C(sp 3 )-O Hydrogenolysis via a Remote-Concerted Oxidative Addition and Its Application to Degradation of a Bisphenol A-Based Epoxy Resin.

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(sp 3 )-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.