Heptafluorobutyric Acid Catalyzed Cross-Dehydrogenative Coupling of 7-Aminocoumarins with 1,2,4-Triazines: A Straightforward Pathway to 3-Triazinyl-7-aminocoumarins

Ramil F. Fatykhov; Igor A. Khalymbadzha; Ainur D. Sharapov; Anastasia P. Potapova; Anton N. Tsmokalyuk; Vasiliy S. Gaviko

doi:10.1055/s-0042-1751570

Synthesis, Table of Contents

Synthesis 2024; 56(12): 1958-1966
DOI: 10.1055/s-0042-1751570

paper

Heptafluorobutyric Acid Catalyzed Cross-Dehydrogenative Coupling of 7-Aminocoumarins with 1,2,4-Triazines: A Straightforward Pathway to 3-Triazinyl-7-aminocoumarins

Ramil F. Fatykhov ∗

^aUral Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation

,

Igor A. Khalymbadzha ∗

^aUral Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation

,

Ainur D. Sharapov

^aUral Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation

,

Anastasia P. Potapova

^aUral Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation

,

Anton N. Tsmokalyuk

^aUral Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation

,

Vasiliy S. Gaviko

^aUral Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation

^bM. N. Mikheev Institute of Metal Physics of the Ural Branch of the Russian Academy of Sciences, 18 S. Kovalevskaya Str., 620108 Ekaterinburg, Russian Federation

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Abstract

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Abstract

A protocol for C–H/C–H cross-coupling reaction between 7-aminocoumarins and 1,2,4-triazines has been developed. The reaction was carried out under heptafluorobutyric acid catalysis providing products with yield up to 91%. The applicability and scope of the proposed method was demonstrated on 25 compounds containing different substituents both in the triazine ring and at the nitrogen atom of 7-aminocoumarins. The study of the reaction mechanism by EPR and radical trapping suggests that radicals are involved in this transformation.

Key words

7-aminocoumarin - cross-dehydrogenative coupling - 1,2,4-triazine - heptafluorobutyric acid - coumarin fluorophore - single electron transfer

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References

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