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Synlett 2025; 36(12): 1759-1764
DOI: 10.1055/a-2596-9863
DOI: 10.1055/a-2596-9863
letter
Stereoselective Synthesis of Monofluoroalkenes via Photoinduced Direct Monofluoroalkenylation of C(sp³)–H Bonds
Authors
We are grateful for the support from the University Natural Science Research Excellent Youth Project of Anhui Province (2023AH030095).
Abstract
In this study, a method is introduced for the photoinduced direct monofluoroalkenylation of C(sp³)–H bonds. A diverse range of fluoroacrylic acids react smoothly with various C–H substrates, leading to the formation of important monofluoroalkene motifs. Notably, this approach is cost-effective, exhibits high stereoselectivity, and eliminates the need for metal catalysts.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2596-9863.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 26. Februar 2025
Angenommen nach Revision: 29. April 2025
Accepted Manuscript online:
29. April 2025
Artikel online veröffentlicht:
16. Juni 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
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- 17 General Procedure In air, eosin Y (5 mol%), the corresponding fluoro acrylic acids (0.2 mmol, 1.0 equiv.), and DABCO (50 mol%) were added to a Schlenk tube containing a stir bar. The vessel was then evacuated and purged with argon through three cycles. Next, C–H pattern solvents (0.5 mL), CH3CN (0.5 mL), DMSO (0.5 mL), and TBPB (2.0 equiv) were added sequentially using a syringe. The resulting reaction mixture was irradiated with 20 W blue LEDs for 10 h under an argon atmosphere. Finally, the residue was purified by flash chromatography using a mixture of PE and EtOAc.