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

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.