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Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents

Author

Listed:
  • Qianqian Chang

    (Shenzhen Campus of Sun Yat-sen University)

  • Qini Li

    (Shenzhen Campus of Sun Yat-sen University)

  • Yi-Hui Deng

    (Peking University Shenzhen Graduate School
    Shenzhen Bay Laboratory)

  • Tian-Yu Sun

    (Peking University Shenzhen Graduate School
    Shenzhen Bay Laboratory)

  • Yun-Dong Wu

    (Peking University Shenzhen Graduate School
    Shenzhen Bay Laboratory
    Peking University)

  • Leifeng Wang

    (Shenzhen Campus of Sun Yat-sen University)

Abstract

Carbon-heteroatom bond (especially for C-N bond) formation through nickel catalysis has seen significant development. Well-established Ni(0)/Ni(II) redox cycle and photoinduced Ni(I)/Ni(III) redox cycle have been the dominant mechanisms. We report a thermally driven Ni-catalyzed method for C-N bond formation between haloarenes and B2N4 reagents, yielding N,N-dialkylaniline derivatives in good to excellent yields with broad functional group tolerance under base-free conditions. The catalytic protocol is useful for base-sensitive structures and late-stage modifications of complex molecules. Detailed mechanistic studies and density functional theory (DFT) calculations indicate that a Ni(I)/Ni(III) redox cycle is preferred in the C-N coupling process, and B2N4 reagent serves both as a single electron transfer donor and a N,N-dialkylation source.

Suggested Citation

  • Qianqian Chang & Qini Li & Yi-Hui Deng & Tian-Yu Sun & Yun-Dong Wu & Leifeng Wang, 2025. "Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents," Nature Communications, Nature, vol. 16(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-58438-6
    DOI: 10.1038/s41467-025-58438-6
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    References listed on IDEAS

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    1. Marvin Mendel & Teresa M. Karl & Jegor Hamm & Sherif J. Kaldas & Theresa Sperger & Bhaskar Mondal & Franziska Schoenebeck, 2024. "Dynamic stereomutation of vinylcyclopropanes with metalloradicals," Nature, Nature, vol. 631(8019), pages 80-86, July.
    2. Jack A. Terrett & James D. Cuthbertson & Valerie W. Shurtleff & David W. C. MacMillan, 2015. "Switching on elusive organometallic mechanisms with photoredox catalysis," Nature, Nature, vol. 524(7565), pages 330-334, August.
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