Issue 20, 2023

Photocatalytic oxidative cleavage of aryl alkene C[double bond, length as m-dash]C bonds using a uranyl cation

Abstract

Highly efficient photocatalytic oxidative cleavage of aryl alkene C[double bond, length as m-dash]C double bonds was effectively established using uranyl cations under mild conditions. Ketones and carboxylic acids were obtained with this protocol. Excellent substrate scopes were found, and scale-up experiments showed the application prospects. By combining experiments with theoretical calculations, the reaction mechanism based on a uranyl–alkyl peroxy radical (ROO˙) intermediate was proposed for the first time to the best of our knowledge. Kinetics experiments demonstrated that the photoreaction followed zeroth-order kinetics. Moreover, this reaction was successfully carried out under sunlight, providing the potential for energy savings applications.

Graphical abstract: Photocatalytic oxidative cleavage of aryl alkene C [[double bond, length as m-dash]] C bonds using a uranyl cation

Supplementary files

Article information

Article type
Research Article
Submitted
17 Jul 2023
Accepted
19 Aug 2023
First published
22 Aug 2023

Org. Chem. Front., 2023,10, 5130-5137

Photocatalytic oxidative cleavage of aryl alkene C[double bond, length as m-dash]C bonds using a uranyl cation

S. Tang, S. Zhang, W. Li, Y. Jiang, Z. Wang, B. Long and J. Su, Org. Chem. Front., 2023, 10, 5130 DOI: 10.1039/D3QO00940H

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