S <sub>N</sub> 2′-Type Difluoro- and Perfluoroalkylation of <i>gem</i> -Dichlorocyclobutenones Mediated by (DMPU) <sub>2</sub> Zn(Rf) <sub>2</sub>
We report an S<sub>N</sub>2'-type strategy for direct difluoromethylation and perfluoroalkylation of <i>gem</i>-dichlorocyclobutenones using (DMPU)<sub>2</sub>Zn(Rf)<sub>2</sub> reagents. Difluoromethylation proceeds under metal-free conditions, whereas copper catalyst promotes perfluoroalkylation via transmetalation. The method tolerates diverse aryl, heteroaryl, and complex bioactive substrates, yielding chloro-fluoroalkylated cyclobutenones as versatile intermediates for further functionalization. This approach enables rapid access to polyfunctionalized fluorinated four-membered carbocycles, thus enriching the toolkit for the synthesis of fluorinated scaffolds relevant to medicinal chemistry and materials science.
Authors
- Xiaojun Zeng (ORCID: https://orcid.org/0000-0002-9425-4882)
- Cong Li (ORCID: https://orcid.org/0000-0002-3473-952X)
- Bosheng Liu (ORCID: https://orcid.org/0000-0003-1744-3169)
- Xujuan Jiang
- Xiaohong Wen (ORCID: https://orcid.org/0009-0001-9741-4933)
Institutions
- Nanchang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-13
- DOI
- https://doi.org/10.1021/acs.orglett.5c03916
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37