A novel acenaphthoimidazolyidene oxazolinic palladium complex and its efficient catalysis in Suzuki–Miyaura cross-coupling reactions of <i>N</i> -acyl-glutarimides <i>via</i> N–C cleavage

Herein, we synthesized a new Pd-N-heterocyclic carbene (Pd-NHC) complex that featured an acenaphthoimidazolylidene (AnIm) skeleton and 2-phenyl-2-oxazoline. This catalyst exhibited extremely high efficiency in Suzuki-Miyaura couplings between <i>N</i>-acyl-glutarimides and organoboronic acids, affording various aryl ketones in excellent yields with a broad substrate scope and wide functional group compatibility. Notably, the reactions were completed in just 5 hours with only 0.5 mol% of catalyst. In addition, this catalytic system also enables the efficient synthesis of functional molecular intermediates. The catalyst, designed through the synergistic integration of a throw-away ligand and an extended conjugated NHC system, further demonstrates its remarkable potential.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00279f
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

A novel acenaphthoimidazolyidene oxazolinic palladium complex and its efficient catalysis in Suzuki–Miyaura cross-coupling reactions of N -acyl-glutarimides via N–C cleavage

Xiaoting Wu, Qinyue Deng, Fei Xiong, Wanfang Li et al.
Organic & Biomolecular Chemistry
Catalytic Cross-Coupling Reactions
article

A novel acenaphthoimidazolyidene oxazolinic palladium complex and its efficient catalysis in Suzuki–Miyaura cross-coupling reactions of N -acyl-glutarimides via N–C cleavage

Xiaoting Wu, Qinyue Deng, Fei Xiong, Wanfang Li, Tenglong Lin, Xiaohu Liu, Xiaojun Lv, Han Shao
article en

Abstract

Herein, we synthesized a new Pd-N-heterocyclic carbene (Pd-NHC) complex that featured an acenaphthoimidazolylidene (AnIm) skeleton and 2-phenyl-2-oxazoline. This catalyst exhibited extremely high efficiency in Suzuki-Miyaura couplings between <i>N</i>-acyl-glutarimides and organoboronic acids, affording various aryl ketones in excellent yields with a broad substrate scope and wide functional group compatibility. Notably, the reactions were completed in just 5 hours with only 0.5 mol% of catalyst. In addition, this catalytic system also enables the efficient synthesis of functional molecular intermediates. The catalyst, designed through the synergistic integration of a throw-away ligand and an extended conjugated NHC system, further demonstrates its remarkable potential.

Organic & Biomolecular ChemistryVol. 23(17)
University of Shanghai for Science and Technology (CN), Shanghai Jiao Tong University (CN)
Openalex Percentile: Top 96%
Catalytic Cross-Coupling Reactions
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A novel acenaphthoimidazolyidene oxazolinic palladium complex and its efficient catalysis in Suzuki–Miyaura cross-coupling reactions of <i>N</i> -acyl-glutarimides <i>via</i> N–C cleavage — Xiaoting Wu, Qinyue Deng, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS