Carbofluorination via a palladium-catalyzed cascade reaction

Marie Gabrielle Braun, Matthew H. Katcher, Abigail G. Doyle*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    59 Scopus citations

    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.

    Original languageEnglish (US)
    Pages (from-to)1216-1220
    Number of pages5
    JournalChemical Science
    Volume4
    Issue number3
    DOIs
    StatePublished - Feb 4 2013

    ASJC Scopus subject areas

    • Chemistry(all)

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