Ni-Catalyzed [2 + 2 + 2] Cycloaddition via the Capture of Azametallacyclopentadienes with Allyl Boronate: Facile Access to Fused Pyridine Derivatives

An unprecedented nickel-catalyzed [2 + 2 + 2] cycloaddition that enables efficient construction of fused pyridine frameworks with allyl boronate was reported. This transformation is proposed to occur through a mechanism involving aza-nickelacyclopentadiene intermediates, wherein the boryl group of the allyl boronate plays a critical role in enabling the following cyclization via the control experiments. This work not only expands the structural diversity accessible via transition-metal-catalyzed [2 + 2 + 2] cycloadditions but also showcases the untapped potential of unsaturated substrates in cycloaddition reactions.

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Publication Details

Journal
Molecules
Published
2025-09-05
DOI
https://doi.org/10.3390/molecules30173629
Citations
2
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
1.87

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article

Ni-Catalyzed [2 + 2 + 2] Cycloaddition via the Capture of Azametallacyclopentadienes with Allyl Boronate: Facile Access to Fused Pyridine Derivatives

Jiuzhong Huang, Tongtong Shi, Ke‐Si Du, S.Z. Hu et al.
2 citations
Molecules
Cyclopropane Reaction Mechanisms
1.87
article

Ni-Catalyzed [2 + 2 + 2] Cycloaddition via the Capture of Azametallacyclopentadienes with Allyl Boronate: Facile Access to Fused Pyridine Derivatives

Jiuzhong Huang, Tongtong Shi, Ke‐Si Du, S.Z. Hu, Ruihuan Gao, Tao Zhu, Zhao‐Yang Wang, Guangyu Li, Chunsheng Li
article en
2 citations

Abstract

An unprecedented nickel-catalyzed [2 + 2 + 2] cycloaddition that enables efficient construction of fused pyridine frameworks with allyl boronate was reported. This transformation is proposed to occur through a mechanism involving aza-nickelacyclopentadiene intermediates, wherein the boryl group of the allyl boronate plays a critical role in enabling the following cyclization via the control experiments. This work not only expands the structural diversity accessible via transition-metal-catalyzed [2 + 2 + 2] cycloadditions but also showcases the untapped potential of unsaturated substrates in cycloaddition reactions.

MoleculesVol. 30(17)
Guiyang Medical University (CN), Zhaoqing University (CN), South China Normal University (CN), Gannan Medical University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Jiangxi Province
Openalex Percentile: Top 14%
Cyclopropane Reaction Mechanisms
1.87
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Ni-Catalyzed [2 + 2 + 2] Cycloaddition via the Capture of Azametallacyclopentadienes with Allyl Boronate: Facile Access to Fused Pyridine Derivatives — Jiuzhong Huang, Tongtong Shi, et al. · Molecules (2025) | TGRS Research Map | TGRS