Issue 13, 2022

Photoredox/persistent radical cation dual catalysis for alkoxy radical generation from alcohols

Abstract

In this report, we present a mild and general strategy for the direct generation of alkoxy radicals from simple aliphatic alcohols enabled by visible-light-induced photoredox/persistent radical cation dual catalysis. The dual catalytic system can trigger alkoxy radical-mediated redox-neutral transformations, avoiding any metal catalysts and the requirement of proximal electron-rich arene moieties on the alcohol substrates. By employing this synergistic catalysis, the Giese reactions of diverse alcohols with electron-deficient alkenes via selective C–C bond scission of the corresponding alkoxy radical intermediates have been achieved. Different from the existing PCET and LMCT processes, mechanistic studies suggest the intermolecular reaction of thianthrene radical cations with alcohols and the subsequent single-electron reduction induced S–O bond homolysis of the formed 5-alkoxythianthrenium cations as the key steps to furnish alkoxy radicals.

Graphical abstract: Photoredox/persistent radical cation dual catalysis for alkoxy radical generation from alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
31 Mar 2022
Accepted
10 May 2022
First published
13 May 2022

Org. Chem. Front., 2022,9, 3532-3539

Photoredox/persistent radical cation dual catalysis for alkoxy radical generation from alcohols

Y. Xiong, X. Zhang, H. Guo and X. Wu, Org. Chem. Front., 2022, 9, 3532 DOI: 10.1039/D2QO00528J

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