Cambridge Open Engage home
What is Cambridge Open Engage?
How to Submit
Browse
About
News [opens in a new tab]

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

Title
Description
Actions
Title
Supporting Information
Description
Experimental and computational details are described in this Supporting Information.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

Version History

Aug 30, 2023 Version 2

Version Notes

Some typos have been corrected.

Metrics

1,940
765
0
Views
Downloads
Citations

License

CC logo
CC
BY logo
BY
NC logo
NC
ND logo
ND
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

Share