Sulfinate-Promoted Defluorinative Cyclization of Polyfluoroalkyl Tetralones Enabled by Photocatalysis
A Ru-catalyzed defluorinative cyclization of polyfluoroalkyl tetralones has been developed under visible-light irradiation for the precise assembly of γ-pyrones featuring α-perfluoroalkyl and β-fluorine substituents. Selective functionalization of five C(sp<sup>3</sup>)-F bonds at three carbon sites on the perfluoroalkyl chain provides a new mode for utilizing polyfluorides as versatile synthons to access difficult-to-obtain heterocyclic scaffolds. Moreover, the sulfinate salt serves dual roles as an oxygen source for creating the carbonyl group and as a defluorinating promoter.
Authors
- Xue‐Qiang Chu (ORCID: https://orcid.org/0000-0002-9173-1508)
- Zhi‐Liang Shen (ORCID: https://orcid.org/0000-0002-3365-9288)
- Hao Xu (ORCID: https://orcid.org/0000-0002-6069-3246)
- Mengtao Ma (ORCID: https://orcid.org/0000-0001-9629-6464)
- Xiaoxiao Sun (ORCID: https://orcid.org/0000-0003-3301-3118)
- Ming-Yao Tang
Institutions
- Nanjing Tech University (CN)
- Nanjing Forestry University (CN)
- Fluorochem (United States) (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-03
- DOI
- https://doi.org/10.1021/acs.orglett.5c00214
- Citations
- 8
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 6.33
Funders
- Nanjing Tech University