Issue 8, 2022

Photocatalytic redox-neutral arylation of cyclopropanols with cyanoarenes via radical-mediated C–C and C–CN bond cleavage

Abstract

β-Arylated ketones widely exist in many biologically active molecules and natural products. Herein, we describe a photocatalytic redox-neutral arylation of cyclopropanols with cyanoarenes via radical-mediated C–C and C–CN bond cleavage to afford various β-arylated ketones. This mild and external oxidant-free approach showed good compatibility with a range of cyclopropanols and cyanoarenes and accomplished absolute regioselective control for the precise functionalization of pyridines via the C–CN bond cleavage of 4-cyanopyridines. Remarkably, this photocatalytic ring-opening of cyclopropanols was enabled by proton-coupled electron transfer (PCET) activation using an oxidized photocatalyst.

Graphical abstract: Photocatalytic redox-neutral arylation of cyclopropanols with cyanoarenes via radical-mediated C–C and C–CN bond cleavage

Supplementary files

Article information

Article type
Research Article
Submitted
10 Dec 2021
Accepted
23 Feb 2022
First published
26 Feb 2022

Org. Chem. Front., 2022,9, 2129-2134

Photocatalytic redox-neutral arylation of cyclopropanols with cyanoarenes via radical-mediated C–C and C–CN bond cleavage

Y. Tong, N. Hao, L. Zhang, J. Wei, Z. Zhang, Q. Fu, D. Yi, Y. Mou, J. Wang, X. Pan, L. Yang, S. Wei, L. Zhong and J. Lu, Org. Chem. Front., 2022, 9, 2129 DOI: 10.1039/D1QO01844B

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