Organic Letters
Organic Letters
5 years ago

Regioselective Three-Component Reaction of Pyridine N-Oxides, Acyl Chlorides, and Cyclic Ethers

Regioselective Three-Component Reaction of Pyridine N-Oxides, Acyl Chlorides, and Cyclic Ethers
Nicholas C. O. Tomkinson, Alan R. Kennedy, Steven T. Kay, D. Heulyn Jones, Jayde A. McLellan
A novel three-component reaction of pyridine N-oxides, acyl chlorides, and cyclic ethers is described. Treatment of an electron-deficient 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-labeling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01481

DOI: 10.1021/acs.orglett.7b01481

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