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Electron-Transfer-Induced Intermolecular [2 + 2] Cycloaddition Reactions Based on the Aromatic “Redox Tag” Strategy

2011; American Chemical Society; Volume: 76; Issue: 9 Linguagem: Inglês

10.1021/jo200490q

1520-6904

Yohei Okada, Asaki Nishimoto, Ryoichi Akaba, Kazuhiro Chiba,

Catalytic C–H Functionalization Methods

Novel electron-transfer-induced intermolecular [2+2] cycloaddition reactions between an aliphatic cyclic enol ether and several unactivated olefins have been demonstrated on the basis of the aromatic "redox tag" strategy. The aromatic "redox tag" was oxidized during the formation of the cyclobutane ring, affording the relatively long-lived aromatic radical cation, which was then reduced to complete the overall reaction that constructed the corresponding [2+2] cycloadducts. The aromatic "redox tag" was also found to facilitate electron-transfer-induced cycloreversion reactions of cyclobutane rings.