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

Jones, D. Heulyn and Kay, Steven T. and McLellan, Jayde A. and Kennedy, Alan R. and Tomkinson, Nicholas C. O. (2017) A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers. Organic Letters. ISSN 1523-7060

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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.

    ORCID iDs

    Jones, D. Heulyn, Kay, Steven T. ORCID logoORCID: https://orcid.org/0000-0001-7020-6627, McLellan, Jayde A. ORCID logoORCID: https://orcid.org/0000-0002-3516-4473, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
    • Item type:Article
      ID code:61128
      Dates:
      Date
      Event
      16 June 2017
      Published
      16 June 2017
      Published Online
      13 June 2017
      Accepted
      Keywords:acyl chloride, pyridine N-oxides, cyclic ethers, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
      Subjects:Science > Chemistry
      Department:Faculty of Science > Pure and Applied Chemistry
      Depositing user: Pure Administrator
      Date deposited:28 Jun 2017 10:26
      Last modified:23 Sep 2021 06:14
      Related URLs:
      URI:https://strathprints.strath.ac.uk/id/eprint/61128
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