A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation
Abstract Borylation chemistry plays a crucial role in the development of new synthetic methodologies. However, the reactivity of zinc-boryl species has not been fully explored, particularly in relation to diverse reaction pathways. Here we show that a zinc-boryl species is successfully synthesized f...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-07-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-61062-z |
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| author | Gan Xu Hok Tsun Chan Shuchang Li Tsz Ying Wong Lei Zhang Qichun Zhang Zhenyang Lin Zhenpin Lu |
| author_facet | Gan Xu Hok Tsun Chan Shuchang Li Tsz Ying Wong Lei Zhang Qichun Zhang Zhenyang Lin Zhenpin Lu |
| author_sort | Gan Xu |
| collection | DOAJ |
| description | Abstract Borylation chemistry plays a crucial role in the development of new synthetic methodologies. However, the reactivity of zinc-boryl species has not been fully explored, particularly in relation to diverse reaction pathways. Here we show that a zinc-boryl species is successfully synthesized from bis(catecholato)diboron, exhibiting amphiphilic reactivity. This compound acts as a nucleophilic boron anion with methyl iodide and as an electrophile with N,N’-dicyclohexylcarbodiimide, facilitating zinc-boron bond dissociation and generating zinc-carbon and zinc-nitrogen bonds while cleaving carbon-nitrogen double bonds. The enhanced reactivity is likely due to the stronger covalency of the zinc-boron bond. Additionally, the zinc-boryl compound promotes the catalytic diborylation of azobenzene, underscoring its versatility as a reactive intermediate. Density functional theory studies illuminate the electronic structure and reactivity of the zinc-boron bond, providing insights into potential applications in synthetic chemistry. |
| format | Article |
| id | doaj-art-a351389e2a1b4aaba5b1fc98da660b18 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-a351389e2a1b4aaba5b1fc98da660b182025-08-20T03:43:27ZengNature PortfolioNature Communications2041-17232025-07-011611810.1038/s41467-025-61062-zA zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylationGan Xu0Hok Tsun Chan1Shuchang Li2Tsz Ying Wong3Lei Zhang4Qichun Zhang5Zhenyang Lin6Zhenpin Lu7Department of Chemistry, State Key Laboratory of Marine Pollution, City University of Hong KongDepartment of Chemistry, The Hong Kong University of Science and TechnologyDepartment of Chemistry, State Key Laboratory of Marine Pollution, City University of Hong KongDepartment of Chemistry, State Key Laboratory of Marine Pollution, City University of Hong KongDepartment of Materials Science and Engineering, City University of Hong KongDepartment of Materials Science and Engineering, City University of Hong KongDepartment of Chemistry, The Hong Kong University of Science and TechnologyDepartment of Chemistry, State Key Laboratory of Marine Pollution, City University of Hong KongAbstract Borylation chemistry plays a crucial role in the development of new synthetic methodologies. However, the reactivity of zinc-boryl species has not been fully explored, particularly in relation to diverse reaction pathways. Here we show that a zinc-boryl species is successfully synthesized from bis(catecholato)diboron, exhibiting amphiphilic reactivity. This compound acts as a nucleophilic boron anion with methyl iodide and as an electrophile with N,N’-dicyclohexylcarbodiimide, facilitating zinc-boron bond dissociation and generating zinc-carbon and zinc-nitrogen bonds while cleaving carbon-nitrogen double bonds. The enhanced reactivity is likely due to the stronger covalency of the zinc-boron bond. Additionally, the zinc-boryl compound promotes the catalytic diborylation of azobenzene, underscoring its versatility as a reactive intermediate. Density functional theory studies illuminate the electronic structure and reactivity of the zinc-boron bond, providing insights into potential applications in synthetic chemistry.https://doi.org/10.1038/s41467-025-61062-z |
| spellingShingle | Gan Xu Hok Tsun Chan Shuchang Li Tsz Ying Wong Lei Zhang Qichun Zhang Zhenyang Lin Zhenpin Lu A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation Nature Communications |
| title | A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation |
| title_full | A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation |
| title_fullStr | A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation |
| title_full_unstemmed | A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation |
| title_short | A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation |
| title_sort | zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation |
| url | https://doi.org/10.1038/s41467-025-61062-z |
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