Transition-Metal-Free C-H/C-Li Coupling of Nonaromatic 2 H-Imidazole 1-Oxides with Pentafluorophenyl Lithium in the Design of Novel Fluorophores with Intramolecular Charge Transfer Effect

Transition-Metal-Free C-H/C-Li Coupling of Nonaromatic 2 H-Imidazole 1-Oxides with Pentafluorophenyl Lithium in the Design of Novel Fluorophores with Intramolecular Charge Transfer Effect / T. D. Moseev, M. V. Varaksin, D. A. Gorlov [et al.] // Journal of Organic Chemistry. – 2020. – Vol. 85, No. 17. – P. 11124-11133.

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2020

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Аннотация

Methodology of nucleophilic substitution of hydrogen (SNH) was first applied for the direct modification of nonaromatic 2H-imidazoles to afford novel polyfluoroarylated azaheterocycles. Scope, tolerance for these transition-metal-free C-H/C-Li coupling reactions, and photophysical properties for the novel 4-(perfluorophenyl)-5-aryl-2H-imidazoles were comprehensively studied. In particular, some of the obtained perfluoroaryl-substituted 2H-imidazoles were found to be of particular interest as promising push-pull fluorophore systems in the design of fluorometric sensor materials due to the effect of intramolecular charge transfer.