4.8 Article

Bioinspired Construction of a Spirocyclohexadienone Moiety via Sodium Nitrite Catalyzed Aerobic Intramolecular Oxidative Phenol Coupling

Journal

ORGANIC LETTERS
Volume 15, Issue 7, Pages 1606-1609

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol400388j

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Funding

  1. National Key Project for Basic Research [2010CB126100]
  2. National Natural Science Foundation of China [21132003, 21121002]
  3. Tianjin Natural Science Foundation [11JCZDJC20500]
  4. National Key Technology Research and Development Program [2011BAE06B05, 2012BAK25B03-3]
  5. Specialized Research Fund for the Doctoral Program of Higher Education [20120031110010]

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An efficient and green intramolecular oxidative phenol coupling for the direct construction of spirocyclohexadienones has been developed, which uses environment-friendly sodium nitrite as the catalyst and oxygen in the air as the terminal oxidant. Hydroxy-containing substituted phenanthrenes and dibenzoazepines could be easily obtained from the dienone-phenol rearrangement.

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