3 years ago

Fe(II)/Au(I) Relay Catalyzed Propargylisoxazole to Pyridine Isomerization: Access to 6-Halonicotinates

Fe(II)/Au(I) Relay Catalyzed Propargylisoxazole to Pyridine Isomerization: Access to 6-Halonicotinates
Firuza M. Shakirova, Ekaterina E. Galenko, Alexander F. Khlebnikov, Alexey V. Galenko, Mikhail S. Novikov
An efficient synthesis of methyl nicotinates/6-halonicotinates by the domino isomerization of 4-propargyl/(3-halopropargyl)-5-methoxyisoxazoles under Fe(II)/Au(I) relay catalysis was developed. It was found that FeNTf2 is an effective catalyst for first step of the domino isomerization, transformation of isoxazole to 2H-azirine, which is compatible with Ph3PAuNTf2, catalyzing the second step.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00736

DOI: 10.1021/acs.joc.7b00736

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