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Selective electrosynthetic hydrocarboxylation of α,β‐unsaturated esters with carbon dioxide

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journal contribution
posted on 10.08.2021, 10:12 authored by Ahmed Sheta, Anas Alkayal, Mohammad Mashaly, Samy Said, Saad Elmorsy, Andrei MalkovAndrei Malkov, Benjamin BuckleyBenjamin Buckley
The carboxylation of low-value commodity chemicals to provide higher-value carboxylic acids is of significant interest. Recently alternative routes to the traditional hydroformylation processes that used potentially toxic carbon monoxide and a transition metal catalyst have appeared. A significant challenge has been the selectivity observed for olefin carboxylation. Photochemical methods have shown a viable route towards the hydrocarboxylation of a,b-unsaturated alkenes but rely on the use of an excess reducing or amine reagent. Herein we report our investigations of an electrochemical approach that is able to hydrocarboxylate a,bunsaturated alkenes with excellent regioselectivity and the ability to carboxylate hindered substrates to afford a-quaternary center carboxylic acids. The reported process requires no chromatography and the products are purified by simple crystallization from the reaction mixture after work-up.

Funding

Underpinning Multi-User Equipment EP/P030599/1

History

School

  • Science

Department

  • Chemistry

Published in

Angewandte Chemie

Volume

60

Issue

40

Pages

21832-21837

Publisher

Wiley

Version

VoR (Version of Record)

Rights holder

© The Authors

Publisher statement

This is an Open Access Article. It is published by Wiley under the Creative Commons Attribution 4.0 Unported Licence (CC BY). Full details of this licence are available at: http://creativecommons.org/licenses/by/4.0/

Acceptance date

02/08/2021

Publication date

2021-09-06

Copyright date

2021

Notes

This is an Open Access Article. It is published by Wiley under the Creative Commons Attribution 4.0 Unported Licence (CC BY). Full details of this licence are available at: http://creativecommons.org/licenses/by/4.0/

ISSN

0044-8249

eISSN

1521-3757

Language

en

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