Stereoselective Synthesis of Monofluoroalkenes via Photoinduced Direct Monofluoroalkenylation of C(sp³)–H Bonds

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.

Key words

monofluoroalkenes - photoinduced - C(sp³)–H - fluoroacrylic acids - decarboxylation

Publikationsverlauf

Eingereicht: 26. Februar 2025

Angenommen nach Revision: 29. April 2025

Accepted Manuscript online:
29. April 2025

Artikel online veröffentlicht:
16. Juni 2025

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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.