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

Timofey D Moseev; Mikhail V Varaksin; Denis A Gorlov; Valery N Charushin; Oleg N Chupakhin

doi:10.1021/acs.joc.0c01042

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

J Org Chem. 2020 Sep 4;85(17):11124-11133. doi: 10.1021/acs.joc.0c01042. Epub 2020 Jul 27.

Authors

Timofey D Moseev¹, Mikhail V Varaksin^{1

2}, Denis A Gorlov¹, Valery N Charushin^{1

2}, Oleg N Chupakhin^{1

2}

Affiliations

¹ Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russia.
² Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620041 Ekaterinburg, Russia.

PMID: 32657130
DOI: 10.1021/acs.joc.0c01042

Abstract

Methodology of nucleophilic substitution of hydrogen (S_N^H) 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.