Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions

Xiu Wang, Zhenhua Wang, Li Liu, Yuya Asanuma, Yasushi Nishihara

    Research output: Contribution to journalArticlepeer-review

    21 Citations (Scopus)

    Abstract

    Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.

    Original languageEnglish
    Article number1671
    JournalMolecules
    Volume24
    Issue number9
    DOIs
    Publication statusPublished - Jan 1 2019

    Keywords

    • Acyl fluorides
    • Carbon-tin bond formation
    • Decarbonylation
    • Nickel
    • Stannylation

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Chemistry (miscellaneous)
    • Molecular Medicine
    • Pharmaceutical Science
    • Drug Discovery
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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