Exploiting a "Beast" in Carbenoid Chemistry: Development of a Straightforward Direct Nucleophilic Fluoromethylation Strategy

Giovanna Parisi, Serena Monticelli, Wolfgang Holzer, Thierry Langer (Corresponding author), Leonardo Degennaro, Vittorio Pace (Corresponding author), Renzo Luisi (Corresponding author), M Colella, G Romanazzi

    Publications: Contribution to journalArticlePeer Reviewed

    Abstract

    The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a "fleeting" lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could: be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

    Original languageEnglish
    Pages (from-to)13648–13651
    Number of pages4
    JournalJournal of the American Chemical Society
    Volume139
    Issue number39
    DOIs
    Publication statusPublished - 4 Oct 2017

    Austrian Fields of Science 2012

    • 104001 General chemistry

    Keywords

    • ALLYLIC ALCOHOLS
    • CARBANIONS
    • ENANTIOSELECTIVE SYNTHESIS
    • FLUORINE
    • FLUOROBIS(PHENYLSULFONYL)METHANE
    • FUNCTIONAL-GROUPS
    • LATE-STAGE
    • MEDICINAL CHEMISTRY
    • MONOFLUOROMETHYLATION
    • PALLADIUM

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