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Palladium-Catalyzed Direct Synthesis of Carbazoles via One-Pot N-Arylation and Oxidative Biaryl Coupling: Synthesis and Mechanistic Study

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 13, Pages 4720-4726

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo9003376

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology of Japan
  2. Japan Society for the Promotion of Science (JPS)
  3. National Institute of Biomedical Innovation (NIBIO)

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An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative Coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.

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