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Issue 3, 2013
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Carbofluorination via a palladium-catalyzed cascade reaction

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Abstract

This article demonstrates the first examples of tandem C–C and C–F bond formation for the palladium-catalyzed carbofluorination of allenes. The intramolecular Heck-fluorination cascade provides monofluoromethylated heteroarenes, an important class of products in medicinal chemistry. We also describe an intermolecular variant for the three-component coupling of allenes, aryl iodides, and AgF. Mechanistic studies indicate that C–F bond formation occurs by outer sphere attack of fluoride on an allylpalladium fluoride intermediate.

Graphical abstract: Carbofluorination via a palladium-catalyzed cascade reaction

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Publication details

The article was received on 10 Dec 2012, accepted on 04 Jan 2013 and first published on 04 Jan 2013


Article type: Edge Article
DOI: 10.1039/C2SC22198E
Chem. Sci., 2013,4, 1216-1220

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    Carbofluorination via a palladium-catalyzed cascade reaction

    M. Braun, M. H. Katcher and A. G. Doyle, Chem. Sci., 2013, 4, 1216
    DOI: 10.1039/C2SC22198E

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