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.