Issue 24, 2022

Olefin epoxidation using electricity as renewable power in a bromide-mediated electrochemical process

Abstract

Electrochemical bromide-mediated olefin epoxidation is a viable strategy to generate freely available bromine (FAB) in situ while minimizing process waste by avoiding chemical oxidants and reducing the use of hazardous reagents. Herein, an electrochemical bromide-mediated olefin epoxidation is presented, wherein bromide plays a double role, as an electrolyte, but also as a mediator that is easily oxidized even at moderate anodic voltage. A quaternary ammonium salt is introduced as an organic electrolyte. The amount of applied charge and the concentrations of electrolyte and olefin were tuned to maximize the efficiency and selectivity of the reaction. Target compounds like 1,2-epoxycyclohexane were obtained in high yields of up to 93%, and a broad substrate scope was demonstrated. Additionally, this process can avoid the formation of dibrominated compounds (e.g., 1,2-dibromocyclohexane), which are typically undesirable dead-end products.

Graphical abstract: Olefin epoxidation using electricity as renewable power in a bromide-mediated electrochemical process

Supplementary files

Article information

Article type
Paper
Submitted
02 Aug 2022
Accepted
11 Nov 2022
First published
22 Nov 2022

Green Chem., 2022,24, 9565-9569

Olefin epoxidation using electricity as renewable power in a bromide-mediated electrochemical process

H. Tang, J. R. Vanhoof and D. De Vos, Green Chem., 2022, 24, 9565 DOI: 10.1039/D2GC02883B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements