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

Alexey V GalenkoFiruza M ShakirovaEkaterina E GalenkoMikhail S Novikov Alexander F Khlebnikov

Published in: The Journal of organic chemistry (2017)

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.

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