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A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation

Author

Listed:
  • Gan Xu

    (City University of Hong Kong)

  • Hok Tsun Chan

    (The Hong Kong University of Science and Technology)

  • Shuchang Li

    (City University of Hong Kong)

  • Tsz Ying Wong

    (City University of Hong Kong)

  • Lei Zhang

    (City University of Hong Kong)

  • Qichun Zhang

    (City University of Hong Kong)

  • Zhenyang Lin

    (The Hong Kong University of Science and Technology)

  • Zhenpin Lu

    (City University of Hong Kong)

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.

Suggested Citation

  • Gan Xu & Hok Tsun Chan & Shuchang Li & Tsz Ying Wong & Lei Zhang & Qichun Zhang & Zhenyang Lin & Zhenpin Lu, 2025. "A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation," Nature Communications, Nature, vol. 16(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-61062-z
    DOI: 10.1038/s41467-025-61062-z
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    References listed on IDEAS

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    1. Sean F. McWilliams & Daniël L. J. Broere & Connor J. V. Halliday & Samuel M. Bhutto & Brandon Q. Mercado & Patrick L. Holland, 2020. "Author Correction: Coupling dinitrogen and hydrocarbons through aryl migration," Nature, Nature, vol. 586(7828), pages 10-10, October.
    2. Sean F. McWilliams & Daniël L. J. Broere & Connor J. V. Halliday & Samuel M. Bhutto & Brandon Q. Mercado & Patrick L. Holland, 2020. "Coupling dinitrogen and hydrocarbons through aryl migration," Nature, Nature, vol. 584(7820), pages 221-226, August.
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