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

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

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2024, Volume: 142, Article number : 155102, Pages count : DOI: 10.1016/j.tetlet.2024.155102

Authors

Paveliev Stanislav A. ¹ , Ustyuzhanin Alexander O. ¹ , Sharygin Alexey A. ^2,1 , Terent'ev Alexander O. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2	Department of Chemistry, Lomonosov Moscow State University, 1 Leninskie Gory, Moscow 119991, Russian Federation

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.

Paveliev S.A. , Ustyuzhanin A.O. , Sharygin A.A. , Terent'ev A.O.
g-C3N4-Catalyzed photochemical synthesis of trifluoromethylated gem-difluoroalkenes from α-trifluoromethyl styrenes and CF3SO2Na
Tetrahedron Letters. 2024. V.142. 155102 . DOI: 10.1016/j.tetlet.2024.155102 WOS Scopus OpenAlex

Web of science:	WOS:001241872700001
Scopus:	2-s2.0-85192809723
OpenAlex:	W4396726259

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