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

• Published in: Tetrahedron letters Vol. 142; pp. 155102 - 155105
• Main Authors: Paveliev, Stanislav A., Ustyuzhanin, Alexander O., Sharygin, Alexey A., Terent'ev, Alexander O.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 06.06.2024; Elsevier
• Subjects: alkenes; Chemistry; Chemistry, Organic; fluorides; gem-Difluoroalkenes; graphene; Graphitic carbon nitride; light; photocatalysis; photocatalysts; Photoredox catalysis; Physical Sciences; Science & Technology; Semiconductors; sodium; Trifluoromethylation; Photoredox catalysis; gem-Difluoroalkenes; Trifluoromethylation; Semiconductors; Graphitic carbon nitride; CDS; gem -Difluoroalkenes; FLUORINE; PHOTOCATALYSTS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2024.155102

[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.