Photoredox-Catalyzed Defluorinative [4 + 2] Cycloaddition of α-Fluoro-β-keto Esters and Alkynes by Single Photosensitizer
A protocol for C-F bond activation using a single organic photocatalyst was developed. The mechanism involves the self-sorting of α-fluorinated-β-keto esters to generate two radicals: one is highly electrophilic and undergoes rapid benzannulation with alkynes to form a series of 1-naphthols; the other is a tertiary carbon radical that serves as a HAT reagent to achieve substrate regeneration. Notably, the released F<sup>-</sup> acts as an endogenous base in the reaction, obviating the need for external additives.
Authors
- Xiaoying Niu
- Haoyuan Li (ORCID: https://orcid.org/0009-0005-0314-9542)
- Qi Meng (ORCID: https://orcid.org/0000-0001-5024-7886)
- Yifan Song (ORCID: https://orcid.org/0000-0002-1621-9555)
- Xiu-Long Yang
- Jincan Zhao
- Rui-Xue Liu
Institutions
- Chinese Academy of Sciences (CN)
- Beijing National Laboratory for Molecular Sciences (CN)
- University of Chinese Academy of Sciences (CN)
- Hebei University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-25
- DOI
- https://doi.org/10.1021/acs.orglett.5c04612
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00