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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

Martinez-Haya, Rebeca ; Marzo, Leyre ; König, Burkhard



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 -ketoesters, -amido esters, and -cyano ketones. Seven membered rings, a frequent structural motif of natural products, are also accessible using this methodology.


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