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

Chiharu Suzuki, Koji Hirano, Tetsuya Satoh* and Masahiro Miura*

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: satohchem.eng.osaka-u.ac.jp, miurachem.eng.osaka-u.ac.jp

C. Suzuki, K. Hirano, T. Satoh, M. Miura, Org. Lett., 2015, 17, 1597-1600.

DOI: 10.1021/acs.orglett.5b00502 (free Supporting Information)


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Abstract

The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant to yield N-H carbazoles. A similar catalytic system can also be used for a dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.

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Key Words

carbazoles, oxygen


ID: J54-Y2015