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Electrooxidative para-selective C–H/N–H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives

Author

Listed:
  • Kun Liu

    (Wuhan University)

  • Shan Tang

    (Wuhan University)

  • Ting Wu

    (Wuhan University)

  • Shengchun Wang

    (Wuhan University)

  • Minzhu Zou

    (Wuhan University)

  • Hengjiang Cong

    (Wuhan University)

  • Aiwen Lei

    (Wuhan University
    Chinese Academy of Sciences)

Abstract

Oxidative C–H/N–H cross-coupling is one of the most atom-economical methods for the construction of C–N bonds. However, traditional oxidative C–H/N–H cross-coupling either required the use of strong oxidants or high reaction temperature, which makes it difficult to tolerate redox active functional groups. Herein we describe an external chemical oxidant-free electrooxidative C–H/N–H cross-coupling between electron-rich arenes and diarylamine derivatives. Under undivided electrolytic conditions, a series of triarylamine derivatives are produced from electron-rich arenes and diarylamine derivatives with high functional group tolerance. Both of the coupling partners are redox active in oxidative C–H/N–H cross-coupling, which enables high regioselectivity in C–N bond formation. Exclusive para-selectivity is observed for the coupling with anilines.

Suggested Citation

  • Kun Liu & Shan Tang & Ting Wu & Shengchun Wang & Minzhu Zou & Hengjiang Cong & Aiwen Lei, 2019. "Electrooxidative para-selective C–H/N–H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-08414-8
    DOI: 10.1038/s41467-019-08414-8
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