Issue 7, 2024

Photoinduced N-heterocyclic nitrenium-catalyzed single electron reduction of Se–Se bond for the generation of nucleophilic selenolates

Abstract

The use of diselenides and alkyl halides in reductive conditions represents a potent approach for synthesizing diverse un-symmetrical selenides. Nonetheless, current methods suffer from drawbacks due to the requirement of stoichiometric re-ductants. In this research, we introduce a new and straightforward photoinduced N-heterocyclic nitrenium catalysis as an alternative. This catalytic process enables single electron reduction of Se–Se bonds, leading to the generation of nucleophilic selenolates. Consequently, unsymmetrical selenides can be synthesized efficiently from readily available diselenides and alkyl chlorides.

Graphical abstract: Photoinduced N-heterocyclic nitrenium-catalyzed single electron reduction of Se–Se bond for the generation of nucleophilic selenolates

Supplementary files

Article information

Article type
Research Article
Submitted
05 Dec 2023
Accepted
13 Feb 2024
First published
15 Feb 2024

Org. Chem. Front., 2024,11, 2070-2074

Photoinduced N-heterocyclic nitrenium-catalyzed single electron reduction of Se–Se bond for the generation of nucleophilic selenolates

C. Zhang, K. Chen, L. Zhou, Z. Yang, Z. Wang and X. Chen, Org. Chem. Front., 2024, 11, 2070 DOI: 10.1039/D3QO02012F

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