4.7 Article

Synthesis of Benzidine Derivatives via FeCl3•6H2O-Promoted Oxidative Coupling of Anilines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 11, Pages 5218-5226

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo4002504

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Funding

  1. Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry, Partenariats Hubert Curien Xu Guangqi [27967RE]
  2. Fundamental Reseach Funds for the Central Universities [CDJRC10220004, CDJZR1122000S]
  3. State Key Laboratory of Elemento-organic Chemistry, Nankai University [201201]
  4. National Natural Science Foundation of China [21273292]

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Under open-flask conditions in the presence of commercially available FeCl3 center dot 6H(2)O, N,N-disubstituted anilines can be converted into diversely functionalized benzidines with yields of up to 99%. Oxidative coupling was extended to N-monosubstituted anilines, and the method was applied to the efficient preparation of 6,6'-biquinoline. Mechanistic investigations have also been performed to explain the observed reactivities.

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