PPh3-assisted esterification of acyl fluorides with ethers via C(Sp3 )–O bond cleavage accelerated by TBAT

Zhenhua Wang, Xiu Wang, Yasushi Nishihara

    Research output: Contribution to journalArticlepeer-review

    9 Citations (Scopus)

    Abstract

    We describe the (triphenylphosphine (PPh3)-assisted methoxylation of acyl fluorides with cyclopentyl methyl ether (CPME) accelerated by tetrabutylammonium difluorotriphenysilicate (TBAT) via regiospecific C–OMe bond cleavage. Easily available CPME is utilized not only as the solvent, but a methoxylating agent in this transformation. The present method is featured by C–O and C–F bond cleavage under metal-free conditions, good functional-group tolerance, and wide substrate scope. Mechanistic studies revealed that the radical process was not involved.

    Original languageEnglish
    Article number574
    JournalCatalysts
    Volume9
    Issue number7
    DOIs
    Publication statusPublished - Jul 2019

    Keywords

    • Acyl fluorides
    • Carbon-oxygen bond cleavage
    • Cyclopentyl methyl ether (CPME)
    • Esterification
    • Tetrabutylammonium difluorotriphenysilicate (TBAT)

    ASJC Scopus subject areas

    • Catalysis
    • Physical and Theoretical Chemistry

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