g-C3N4-Catalyzed photochemical synthesis of trifluoromethylated gem-difluoroalkenes from α-trifluoromethyl styrenes and CF3SO2Na

[Display omitted] Trifluoromethyl-substituted gem-difluoroalkenes were synthesized via the reaction of α-trifluoromethyl styrenes with trifluoromethyl radical derived from sodium trifluoromethylsulfinate under the visible light induced graphitic carbon nitride-mediated heterogeneous photocatalysis....

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Bibliographic Details
Published in:Tetrahedron letters 2024-06, Vol.142, p.155102, Article 155102
Main Authors: Paveliev, Stanislav A., Ustyuzhanin, Alexander O., Sharygin, Alexey A., Terent'ev, Alexander O.
Format: Article
Language:English
Subjects:
gem-Difluoroalkenes
Graphitic carbon nitride
Photoredox catalysis
Semiconductors
Trifluoromethylation
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Summary:[Display omitted] Trifluoromethyl-substituted gem-difluoroalkenes were synthesized via the reaction of α-trifluoromethyl styrenes with trifluoromethyl radical derived from sodium trifluoromethylsulfinate under the visible light induced graphitic carbon nitride-mediated heterogeneous photocatalysis. The disclosed process is based on the sequential radical/ionic transformations of α-trifluoromethyl alkenes. The developed approach exploits the dual role of g-C3N4 as a photocatalyst. g-C3N4 acts as an electron acceptor for the generation of CF3 radicals and participates in the reduction of intermediate carbon-centered radical with β-elimination of fluoride anion and formation of the target products.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2024.155102