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

Alexey V Galenko; Firuza M Shakirova; Ekaterina E Galenko; Mikhail S Novikov; Alexander F Khlebnikov

doi:10.1021/acs.joc.7b00736

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

J Org Chem. 2017 May 19;82(10):5367-5379. doi: 10.1021/acs.joc.7b00736. Epub 2017 May 5.

Authors

Alexey V Galenko¹, Firuza M Shakirova¹, Ekaterina E Galenko¹, Mikhail S Novikov¹, Alexander F Khlebnikov¹

Affiliation

¹ Saint Petersburg State University , Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg, 199034 Russia.

PMID: 28452217
DOI: 10.1021/acs.joc.7b00736

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't