Palladium-catalyzed decarboxylation of vinyloxazolidine-2,4-diones used in the divergent reaction with 2-alkynylphenols and 2-alkynylanilines
The <i>in situ</i> generated aza-π-allylpalladium species, formed <i>via</i> the palladium-catalyzed decarboxylation of vinyloxazolidine-2,4-diones, were successfully used for the divergent reaction with 2-alkynylphenols and 2-alkynylanilines. Using Pd<sub>2</sub>(dba)<sub>3</sub>·CHCl<sub>3</sub> as the catalyst and Cu(OTf)<sub>2</sub> as the additive, a range of 2,3-disubstituted benzofurans and indoles were obtained in moderate to excellent yields. However, when PPh<sub>3</sub> ligand was added, a series of γ-<i>O</i>/<i>N</i>-substituted α,β-unsaturated amides were obtained in acceptable yields. This reaction demonstrates that vinyloxazolidine-2,4-diones are capable of undergoing palladium-catalyzed decarboxylative allylic functionalization with carbon, oxygen, and nitrogen nucleophiles.
Authors
- Ming‐Qiang Zhou
- Jian‐Qiang Zhao (ORCID: https://orcid.org/0000-0002-4444-9630)
- Zhen‐Hua Wang (ORCID: https://orcid.org/0000-0002-0603-707X)
- Wei‐Cheng Yuan (ORCID: https://orcid.org/0000-0003-4850-8981)
- Yanping Zhang (ORCID: https://orcid.org/0000-0001-8150-7265)
- Yong You (ORCID: https://orcid.org/0000-0002-4689-0235)
- Zhonglie Yang
Institutions
- Chinese Academy of Sciences (CN)
- Chengdu Organic Chemicals (China) (CN)
- Chengdu University (CN)
- Chengdu Institute of Biology (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00051c
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00