Competition of the Addition/Cycloaddition Schemes in the Reaction Between Fluorinated Nitrones and Arylacetylenes: Comprehensive Experimental and DFT Study
The course of the reactions of acetylenes with fluorinated nitrones in the presence of Zn(OTf)<sub>2</sub> and Et<sub>2</sub>Zn was investigated. The formation of hydroxylamines and/or 1,2-oxazolines as products was observed. The desired hydroxylamines were formed as main products if reactions were carried out with the usage of Et<sub>2</sub>Zn. In order to explain the obtained results, quantum mechanical calculations of the reaction paths leading to both products were carried out. Further research allowed us to develop the enantioselective variant of described reactions with the usage of enantiomerically pure AziPhenol ligand bearing chiral aziridine scaffold.
Authors
- Radomir Jasiński (ORCID: https://orcid.org/0000-0001-8555-6793)
- Szymon Jarzyński (ORCID: https://orcid.org/0000-0002-1558-098X)
- Anna Pietrzak (ORCID: https://orcid.org/0000-0003-3415-8650)
- Emilia Obijalska (ORCID: https://orcid.org/0000-0002-4160-2580)
- Andrzej Krempiński (ORCID: https://orcid.org/0009-0006-4317-4694)
Institutions
- Lodz University of Technology (PL)
- University of Łódź (PL)
- Cracow University of Technology (PL)
Publication Details
- Journal
- Molecules
- Published
- 2025-11-28
- DOI
- https://doi.org/10.3390/molecules30234578
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Uniwersytet Łódzki
- Infrastruktura PL-Grid
- Academic Computer Centre Cyfronet, AGH University of Science and Technology