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.
Authors
- Xiaoting Wu (ORCID: https://orcid.org/0000-0002-3996-868X)
- Qinyue Deng (ORCID: https://orcid.org/0000-0002-7720-1965)
- Fei Xiong (ORCID: https://orcid.org/0000-0002-1140-994X)
- Wanfang Li (ORCID: https://orcid.org/0000-0002-2544-1756)
- Tenglong Lin (ORCID: https://orcid.org/0009-0006-3998-8644)
- Xiaohu Liu (ORCID: https://orcid.org/0000-0002-0892-7172)
- Xiaojun Lv (ORCID: https://orcid.org/0000-0001-8457-8501)
- Han Shao (ORCID: https://orcid.org/0000-0002-0150-1486)
Institutions
- University of Shanghai for Science and Technology (CN)
- Shanghai Jiao Tong University (CN)
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
- Field-Weighted Citation Impact
- 0.00