Issue 9, 2012

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Apr 2012
Accepted
21 Jun 2012
First published
25 Jun 2012

Chem. Sci., 2012,3, 2807-2811

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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