Catalyst-controlled selective synthesis of pyridines and pyrroles
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- Catalyst-controlled selective synthesis of pyridines and pyrroles
- Jiang, Yaojia; Park, Cheol-Min
- HIGHLY SUBSTITUTED PYRROLES; DIAZO OXIME ETHERS; C-H AMINATION; CASCADE REACTIONS; FUNCTIONALIZED PYRIDINES; 2+2+2 CYCLOADDITION; DIELS-ALDER; BONDS; 2H-AZIRINES; AZIRIDINATION
- Issue Date
- ROYAL SOC CHEMISTRY
- CHEMICAL SCIENCE, v.5, no.6, pp.2347 - 2351
- 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.
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