Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents
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...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-04-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-58438-6 |
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| author | Qianqian Chang Qini Li Yi-Hui Deng Tian-Yu Sun Yun-Dong Wu Leifeng Wang |
| author_facet | Qianqian Chang Qini Li Yi-Hui Deng Tian-Yu Sun Yun-Dong Wu Leifeng Wang |
| author_sort | Qianqian Chang |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-751ebc0522ed4377a54de6c2df489214 |
| institution | DOAJ |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-751ebc0522ed4377a54de6c2df4892142025-08-20T03:07:43ZengNature PortfolioNature Communications2041-17232025-04-0116111110.1038/s41467-025-58438-6Nickel catalyzed C-N coupling of haloarenes with B2N4 reagentsQianqian Chang0Qini Li1Yi-Hui Deng2Tian-Yu Sun3Yun-Dong Wu4Leifeng Wang5School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen UniversitySchool of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen UniversityKey Laboratory of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Shenzhen Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate SchoolKey Laboratory of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Shenzhen Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate SchoolKey Laboratory of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Shenzhen Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate SchoolSchool of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen UniversityAbstract 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.https://doi.org/10.1038/s41467-025-58438-6 |
| spellingShingle | Qianqian Chang Qini Li Yi-Hui Deng Tian-Yu Sun Yun-Dong Wu Leifeng Wang Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents Nature Communications |
| title | Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents |
| title_full | Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents |
| title_fullStr | Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents |
| title_full_unstemmed | Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents |
| title_short | Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents |
| title_sort | nickel catalyzed c n coupling of haloarenes with b2n4 reagents |
| url | https://doi.org/10.1038/s41467-025-58438-6 |
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