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Synthesis 2023; 55(18): 3013-3018
DOI: 10.1055/a-2039-4825
DOI: 10.1055/a-2039-4825
paper
Special Issue Electrochemical Organic Synthesis
Radical Cation [2+2] Cycloadditions Enabled by Surface-Assisted Pseudo-Intramolecular Electron Transfers
This work was supported in part by the Japan Society for the Promotion of Science [JSPS KAKENHI Grant Nos. 16H06193, 17K19221, 22K05450 (to Y.O.), and 21J12556 (to K.N.)] and by the TEPCO Memorial Foundation (to Y.O.).
Abstract
Both intermolecular and intramolecular electron transfers can be the key in the determination of synthetic outcomes of photochemical and electrochemical reactions. Herein, we report dispersed TiO2 nanoparticles in combination with methoxybenzene to be a unique heterogeneous photocatalyst for facilitating the formation of novel cyclobutanes. Although the mechanistic details are as yet unclear, the results described herein imply that methoxybenzene is adsorbed onto the TiO2 surface, coming in close proximity to the forming cyclobutane radical cation, to realize a pseudo-intramolecular electron transfer between the species.
Key words
radical cations - [2+2] cycloaddition - surface-assisted - pseudo-intramolecular process - electron transferSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2039-4825.
- Supporting Information
Publication History
Received: 31 December 2022
Accepted after revision: 21 February 2023
Accepted Manuscript online:
21 February 2023
Article published online:
22 March 2023
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For selected reviews of the alkene-derived radical cation chemistry, see: