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. 2012;3(9):2807-2811.
doi: 10.1039/C2SC20658G. Epub 2012 Jun 25.

Crossed Intermolecular [2+2] Cycloaddition of Styrenes by Visible Light Photocatalysis

Michael A Ischay  1 , Michael S Ament, Tehshik P Yoon
Affiliations

Crossed Intermolecular [2+2] Cycloaddition of Styrenes by Visible Light Photocatalysis

Michael A Ischay et al. Chem Sci. 2012.

Abstract

We report a method for the crossed [2+2] cycloaddition of styrenes using visible light photocatalysis. Few methods for the synthesis of unsymmetrically substituted cyclobutanes by photochemical [2+2] cycloaddition are known. We show that careful tuning of the electrochemical properties of a ruthenium photocatalyst enable the efficient crossed [2+2] cycloaddition of styrenes upon irradiation with visible light. We outline the logic that enables high crossed chemoselectivity, and we also demonstrate that this reaction is remarkably efficient; gram-scale reactions can be conducted with as little as 0.025 mol% of the photocatalyst.

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Figures

Scheme 1
Scheme 1
Reversibility of the [2+2] cycloaddition.
Scheme 2
Scheme 2
Proposed mechanism of crossed cycloaddition
See this image and copyright information in PMC

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