Attack on fluorinated 2-aryloxazolines by organolithiums: Dearomatisation, lithiation or substitution

James Clayton, Jonathan Clayden

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Treatment of 4-, 3- or 2-aryl-4,5-diphenyloxazolines with isopropyllithium gives the products of dearomatising addition, fluorine-directed lithiation or nucleophilic aromatic substitution of fluoride depending on substitution pattern and conditions. In the case of the 4-fluoroaryl substrates, fluorinated 1,4-cyclohexadiene may be obtained in good yield. © 2011 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)2436-2439
    Number of pages3
    JournalTetrahedron Letters
    Volume52
    Issue number19
    DOIs
    Publication statusPublished - 11 May 2011

    Keywords

    • Carbolithiation
    • Dearomatisation
    • Metallation
    • Organofluorine chemistry
    • Oxazoline
    • Synthesis

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