Issue 6, 2014

A catalyst-controlled selective synthesis of pyridines and pyrroles

Abstract

We have developed a dual reaction manifold that enables the selective synthesis of both pyridines and pyrroles from the common substrates α-diazo oxime ethers. The strong propensity of 1,3-dienyl nitrenes for 4π-electrocyclization to give pyrroles could be diverted to 6π-electrocyclization via a 1,6-hydride shift or prototropic isomerization, leading to the exclusive formation of pyridines by employing metal nitrene complexes derived from α-diazo oxime ethers under Rh(II) catalysis. Furthermore, an orthogonal catalytic system has been identified that promotes the selective formation of 1H-pyrroles from the same substrates by redirecting the reactivity of vinyl 2H-azirine intermediates.

Graphical abstract: A catalyst-controlled selective synthesis of pyridines and pyrroles

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Jan 2014
Accepted
12 Feb 2014
First published
12 Feb 2014

Chem. Sci., 2014,5, 2347-2351

Author version available

A catalyst-controlled selective synthesis of pyridines and pyrroles

Y. Jiang and C. Park, Chem. Sci., 2014, 5, 2347 DOI: 10.1039/C4SC00125G

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