Direct and Chemoselective Synthesis of Tertiary Difluoroketones via Weinreb Amide Homologation with a CHF2-Carbene Equivalent

Margherita Miele, Andrea Citarella, Nicola Micale, Wolfgang Holzer, Vittorio Pace

    Publications: Contribution to journalArticlePeer Reviewed

    Abstract

    The homologation of Weinreb amides into difluoromethylketones with a formal nucleophilic CHF2 transfer agent is reported. Activating TMSCHF2 with potassium tert-amylate enables a convenient access to the difluorinated homologation reagent, which adds to the acylating partners. The high chemoselectivity showcased in the presence of variously multifunctionalized Weinreb amides, jointly with uniformly high yields, enables the strategy of general applicability without requiring any stabilization element for the putative carbanion.

    Original languageEnglish
    Pages (from-to)8261-8265
    Number of pages5
    JournalOrganic Letters
    Volume21
    Issue number20
    DOIs
    Publication statusPublished - 18 Oct 2019

    Austrian Fields of Science 2012

    • 104015 Organic chemistry

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