A zinc boryl compound unlocks diverse reactivity pathways beyond nucleophilic borylation

Gan Xu, Hok Tsun Chan, Shuchang Li, Tsz Ying Wong, Lei Zhang, Qichun Zhang, Zhenyang Lin () and Zhenpin Lu ()
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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

Nature Communications, 2025, vol. 16, issue 1, 1-8

Abstract: 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.

Date: 2025
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DOI: 10.1038/s41467-025-61062-z

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