Direct synthesis of N-H carbazoles via iridium(III)-catalyzed intramolecular C-H amination

Chiharu Suzuki; Koji Hirano; Tetsuya Satoh; Masahiro Miura

doi:10.1021/acs.orglett.5b00502

Direct synthesis of N-H carbazoles via iridium(III)-catalyzed intramolecular C-H amination

Org Lett. 2015 Mar 20;17(6):1597-600. doi: 10.1021/acs.orglett.5b00502. Epub 2015 Mar 11.

Authors

Chiharu Suzuki¹, Koji Hirano¹, Tetsuya Satoh^{1

2}, Masahiro Miura¹

Affiliations

¹ †Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
² ‡JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.

PMID: 25760543
DOI: 10.1021/acs.orglett.5b00502

Abstract

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.