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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| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
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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| Summary: | 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. |
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| ISSN: | 2041-1723 |