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Issue 82, 2018
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Reinventing the De Mayo reaction: synthesis of 1,5-diketones or 1,5-ketoesters via visible light [2+2] cycloaddition of β-diketones or β-ketoesters with styrenes

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Abstract

A visible light mediated De Mayo reaction between 1,3-diketones and styrenes following a [2+2] cycloaddition pathway via a photosensitization mechanism gives access to 1,5-diketones. The reaction has been applied to substituted styrenes and aryl- and alkyl-substituted ketones. Moreover, the method converts β-ketoesters, β-amido esters, and β-cyano ketones. Seven membered rings, a frequent structural motif of natural products, are also accessible using this methodology.

Graphical abstract: Reinventing the De Mayo reaction: synthesis of 1,5-diketones or 1,5-ketoesters via visible light [2+2] cycloaddition of β-diketones or β-ketoesters with styrenes

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Publication details

The article was received on 30 Aug 2018, accepted on 20 Sep 2018 and first published on 20 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC07044J
Citation: Chem. Commun., 2018,54, 11602-11605
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    Reinventing the De Mayo reaction: synthesis of 1,5-diketones or 1,5-ketoesters via visible light [2+2] cycloaddition of β-diketones or β-ketoesters with styrenes

    R. Martinez-Haya, L. Marzo and B. König, Chem. Commun., 2018, 54, 11602
    DOI: 10.1039/C8CC07044J

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