Rhodium(III)-Catalyzed C–H/N–H Alkyne Annulation of Nonsymmetric 2-Aryl (Benz)imidazole Derivatives: Photophysical and Mechanistic Insights
Gleiston G. Dias, Esther R. S. Paz, Juliana Y. Kadooca, Adão A. Sabino, L. A. Cury, Kohei Torikai, Carlos A. de Simone, Felipe Fantuzzi, Eufrânio N. da Silva Júnior
Abstract
Rhodium(III) catalysis enabled C-H/N-H alkyne annulation of nonsymmetric imidazole derivatives. This study encompasses the synthesis of imidazoles from a naturally occurring quinoidal compound and their use for the preparation of rigid π-extended imidazole derivatives with outstanding fluorescence. Our study also brings to light the photophysical aspects and the mechanism of the reaction studied via computational calculations. This method provided an efficient and versatile tool for the synthesis of fluorescent compounds with a wide range of chemical and biological applications.
Topics & Concepts
AnnulationChemistryAlkyneRhodiumImidazoleArylCatalysisCombinatorial chemistryFluorescenceChemical synthesisStereochemistryOrganic chemistryIn vitroBiochemistryQuantum mechanicsPhysicsAlkylCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesSynthesis and Catalytic Reactions