Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles

Kenji Matsumoto, Yasunori Toubaru, Shohei Tachikawa, Ayaka Miki, Kentaro Sakai, Syota Koroki, Tsukasa Hirokane, Mitsuru Shindo, Masahiro Yoshida

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, a heterogeneous rhodium-catalyzed oxidative homocoupling reaction of anilines utilizing molecular oxygen as the sole oxidant is reported. Employing a commercially available and recyclable Rh/C catalyst enabled the oxidative dimerization of various anilines, including N,N-disubstituted and N-monosubstituted anilines, as well as diarylamines, triarylamines, and carbazoles. Additionally, the catalytic protocol was extended to the ortho-ortho coupling of anilines, affording 2,2′-diaminobiphenyls with high regioselectivity. Notably, the developed approach provides rapid access to diversely functionalized benzidines and diaminobiphenyls in an operationally simple, practical, and environmentally friendly manner.

Original languageEnglish
Pages (from-to)15154-15166
Number of pages13
JournalJournal of Organic Chemistry
Volume85
Issue number23
DOIs
Publication statusPublished - Dec 4 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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