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Issue 9, 2012
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Crossed intermolecular [2 + 2] cycloaddition of styrenes by visible light photocatalysis

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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.

Graphical abstract: Crossed intermolecular [2 + 2] cycloaddition of styrenes by visible light photocatalysis

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Supplementary files

Article information


Submitted
21 Apr 2012
Accepted
21 Jun 2012
First published
25 Jun 2012

Chem. Sci., 2012,3, 2807-2811
Article type
Edge Article

Crossed intermolecular [2 + 2] cycloaddition of styrenes by visible light photocatalysis

M. A. Ischay, M. S. Ament and T. P. Yoon, Chem. Sci., 2012, 3, 2807
DOI: 10.1039/C2SC20658G

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