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Issue 6, 2014

A catalyst-controlled selective synthesis of pyridines and pyrroles

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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


Submitted
13 Jan 2014
Accepted
12 Feb 2014
First published
12 Feb 2014

Chem. Sci., 2014,5, 2347-2351
Article type
Edge Article
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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