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<p>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 B<sub>2</sub>N<sub>4</sub> reagents, yielding <i>N,N</i>-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 B<sub>2</sub>N<sub>4</sub> reagent serves both as a single electron transfer donor and a <i>N</i>,<i>N</i>-dialkylation source.</p>

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Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年4月3日

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  • Qianqian Chang,
  • Qini Li,
  • Yi-Hui Deng,
  • Tian-Yu Sun,
  • Yun-Dong Wu,
  • Leifeng Wang

摘要

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.