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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.

SUBMITTER: Ischay MA

PROVIDER: S-EPMC3439822 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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

Ischay Michael A MA Ament Michael S MS Yoon Tehshik P TP

Chemical science 20120625 9

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 demonstra ...[more]

PMID: 22984640

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