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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
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Nickel
Chemical recycling
Epoxy resin

Supplementary materials

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

Aug 30, 2023 Version 2

Version Notes

Some typos have been corrected.

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-dz9v9-v2
D O I: 10.26434/chemrxiv-2023-dz9v9-v2 [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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