Radical Cation [2+2] Cycloadditions Enabled by Surface-Assisted Pseudo-Intramolecular Electron Transfers

Sota Adachi; Naoya Maeta; Kaii Nakayama; Zimo Wang; Yasuhiro Hashimoto; Yohei Okada

doi:10.1055/a-2039-4825

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(18): 3013-3018
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

Sota Adachi

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Naoya Maeta

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Kaii Nakayama

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Zimo Wang

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Yasuhiro Hashimoto

^bDepartment of Chemical Engineering, Tokyo University of Agriculture and Technology, 2-14-16 Naka-cho, Koganei, Tokyo 184-8588, Japan

,

Yohei Okada ∗

^aDepartment of Applied Biological Science, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan

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Abstract

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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 transfer

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Referenzen

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