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

James Clayton, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2436-2439
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number19
Early online date27 Feb 2011
DOIs
Publication statusPublished - 11 May 2011

Keywords

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

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