4.8 Article

Direct Synthesis of N-H Carbazoles via Iridium(III)-Catalyzed Intramolecular C-H Amination

Journal

ORGANIC LETTERS
Volume 17, Issue 6, Pages 1597-1600

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00502

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Funding

  1. MEXT
  2. JSPS
  3. JST, Japan
  4. Grants-in-Aid for Scientific Research [25288048, 25105733] Funding Source: KAKEN

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The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant through intramolecular direct C-H amination to produce N-H carbazoles. A similar iridium/copper system can also catalyze the unprecedented dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.

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