Issue 3, 2024

Photoredox catalyzed release of carbon-based radicals from 2-substituted-1,3-imidazolidines

Abstract

In the frame of developing easily oxidizable compounds for the photorelease of carbon-based radicals, we describe herein the use of 2-substituted-1,3-imidazolidines. These compounds (Eoxca. 1 V vs. SCE) were used to generate (substituted) alkyl radicals under photoredox conditions. The radicals smoothly added to electron-poor C[double bond, length as m-dash]C bonds for the forging of C(sp3)–C(sp3) bonds under metal-free conditions. Acridinium salts and even 4-CzIPN could be used as photocatalysts thanks to the favorable redox properties of these heterocycles.

Graphical abstract: Photoredox catalyzed release of carbon-based radicals from 2-substituted-1,3-imidazolidines

Supplementary files

Article information

Article type
Research Article
Submitted
07 Nov 2023
Accepted
07 Dec 2023
First published
07 Dec 2023
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2024,11, 661-667

Photoredox catalyzed release of carbon-based radicals from 2-substituted-1,3-imidazolidines

A. Luguera Ruiz, E. Mariani, S. Protti and M. Fagnoni, Org. Chem. Front., 2024, 11, 661 DOI: 10.1039/D3QO01856C

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