Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents

Qianqian Chang, Qini Li, Yi-Hui Deng, Tian-Yu Sun (), Yun-Dong Wu () and Leifeng Wang ()
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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
Tian-Yu Sun: Peking University Shenzhen Graduate School
Yun-Dong Wu: Peking University Shenzhen Graduate School
Leifeng Wang: Shenzhen Campus of Sun Yat-sen University

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: 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.

Date: 2025
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DOI: 10.1038/s41467-025-58438-6

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