Easy Access to 2-Fluoro- and 2-Iodo-2H-azirines via the Halex Reaction

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4 Scopus citations

Abstract

A simple gram-scale method for the preparation of esters and dialkylamides of 2-(fluoro/iodo)-2H-azirine-2-carboxylic acids via the halogen exchange (Halex) reaction of 2-bromo-substituted analogues is reported. The method operates with inexpensive and safe reagents­, Bu4NF and potassium iodide, providing high product yields. Alternatively, 2-fluoro-2H-azirine-2-carboxylates can be prepared from 2-iodo- and 2-chloro-analogues. The latter compounds can be obtained in practically quantitative yield by treating the 2-iodo- and 2-bromo-2H-azirine-2-carboxylic esters with Bu4NCl.
Original languageEnglish
Pages (from-to)4582-4589
JournalSynthesis
Volume51
Issue number24
DOIs
StatePublished - 5 Sep 2019

Scopus subject areas

  • Chemistry(all)

Keywords

  • azirines
  • halogen exchange reaction
  • fluorine
  • Iodine
  • nucleophilic­ substitution

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