Nickel-Catalyzed C(sp3)−O Hydrogenolysis via a Remote Concerted Oxidative Addition and its Application to Degradation of a Bisphenol A-Based Epoxy Resin

30 August 2023, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


In this work, we developed a nickel-catalyzed transfer hydrogenolysis of 1-aryloxy-3-amino-2-propanols, which is a model compound of 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, where BPA was directly recovered from the resin.


Chemical recycling
Epoxy resin

Supplementary materials

Supporting Information
Experimental and computational details are described in this Supporting Information.


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