4.8 Article

Cu-Catalyzed Concise Synthesis of Pyridines and 2-(1H)-Pyridones from Acetaldehydes and Simple Nitrogen Donors

Journal

ORGANIC LETTERS
Volume 17, Issue 3, Pages 584-587

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5035996

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Funding

  1. National Basic Research Program of China (973 Program) [2015CB856600]
  2. National Natural Science Foundation of China [21325206, 21172006]
  3. National Young Top-notch Talent Support Program

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A highly selective copper-catalyzed concise synthesis of 3,5-diarylpyridine and 2-(1H)-pyridone has been achieved through cascade Chichibabin-type cyclization, C(sp(3))-C(sp(3)) cleavage, and aerobic oxidation. Azide, ceric ammonium nitrate (CAN), and 2-aminopyridine are disclosed as efficient nitrogen donors in this Cu-catalysis using O-2 as the oxidant. Water and molecular oxygen were employed as the oxygen source in the case of oxygenation.

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