Issue 13, 2024

Visible-light-driven PCy3-promoted deselenization of 1,2-diselenides

Abstract

Deselenization of 1,2-diselenides offers a promising tool for the construction of organochalcogenides. However, the requirement of transition metals and harsh reaction conditions are still significant challenges in this transformation. Herein, we have developed a metal-free and catalyst-free photocatalytic system for deselenization of 1,2-diselenides with PCy3, providing convenient access to monoselenides under mild conditions. Most importantly, the visible-light-induced protocol allowed for the deselenizative cross-coupling reaction between two different diselenides as well as the deselenizative cross-coupling reaction between a diselenide and a disulfide to provide unsymmetrical monoselenides and sulfides, respectively. DFT computational studies demonstrated that the chemoselectivity in the deselenizative cross-coupling reaction is derived from the difference in the C–Se bond dissociation energies as well as the polarity-matching effect. Mechanistic studies disclosed that the key to the deselenization lies in the generation of carbon-centered radicals through sequential Se–Se bond and C–Se bond cleavage of 1,2-diselenides.

Graphical abstract: Visible-light-driven PCy3-promoted deselenization of 1,2-diselenides

Supplementary files

Article information

Article type
Research Article
Submitted
21 Mar 2024
Accepted
13 May 2024
First published
14 May 2024

Org. Chem. Front., 2024,11, 3630-3638

Visible-light-driven PCy3-promoted deselenization of 1,2-diselenides

Y. Liu, F. Li, M. Liu, Y. Zhou and H. Wu, Org. Chem. Front., 2024, 11, 3630 DOI: 10.1039/D4QO00522H

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