A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers

D. Heulyn Jones, Steven T. Kay, Jayde A. McLellan, Alan R. Kennedy, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

9 Citations (Scopus)
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Abstract

A novel 3-component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers is described. Treatment of an electron defi-cient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25–50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic labelling experiments and substrate scope support the reaction proceeding through a carbene intermediate.
Original languageEnglish
JournalOrganic Letters
Early online date16 Jun 2017
DOIs
Publication statusE-pub ahead of print - 16 Jun 2017

Keywords

  • acyl chloride
  • pyridine N-oxides
  • cyclic ethers

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