A catalyst-controlled selective synthesis of pyridines and pyrroles
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- Title
- A catalyst-controlled selective synthesis of pyridines and pyrroles
- Author
- Jiang, Yaojia; Park, Cheol-Min
- Issue Date
- 2014-06
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- CHEMICAL SCIENCE, v.5, no.6, pp.2347 - 2351
- Abstract
- We have developed a dual reaction manifold that enables selective synthesis of both pyridines and pyrroles from 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 1,6-hydride shift or prototropic isomerization leading to 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 selective formation of 1H-pyrroles from the same substrates by redirecting the reactivity of vinyl 2H-azirine intermediates.
- URI
- https://scholarworks.unist.ac.kr/handle/201301/2412
- URL
- http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84900338682
- DOI
- 10.1039/C4SC00125G
- ISSN
- 2041-6520
- Appears in Collections:
- CHM_Journal Papers
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