Efficient Visible Light Photocatalysis of [2+2] Enone Cycloadditions

Michael A. Ischay, Mary E. Anzovino, Juana Du and Tehshik P. Yoon*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, Email: tyoonchem.wisc.edu

M. A. Ischay, M. E. Anzovino, J. Du, T. P. Yoon, J. Am. Chem. Soc., 2008, 130, 12886-12887.

DOI: 10.1021/ja805387f

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Abstract

Ru(bipy)₃Cl₂ is a visible light photocatalyst for [2+2] enone cycloadditions. Various aryl enones participate readily in the formation of the cyclobutane products, and the diastereoselectivity is excellent. A mechanism is proposed in which a photogenerated Ru(bipy)₃⁺ complex promotes one-electron reduction of the enone substrate, which undergoes subsequent radical anion cycloaddition.

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proposed mechanism

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Crossed Intermolecular [2+2] Cycloadditions of Acyclic Enones via Visible Light Photocatalysis

J. Du, T. P. Yoon, J. Am. Chem. Soc., 2009, 131, 14604-14606.

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Key Words

Cyclobutanes, Cyclopentanes

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ID: J48-Y2008-2680