Rhodium(III)-Catalyzed C–H/N–H Alkyne Annulation of Non-Symmetric 2-Aryl-(Benz)Imidazole Derivatives: Photophysical and Mechanistic Insights

Dias, Gleiston G., Paz, Esther R. S., Kadooca, Juliana Y., Sabino, Adão A., Cury, Luiz A., Torikai, Kohei, de Simone, Carlos A., Fantuzzi, Felipe, da Silva Júnior, Eufrânio N. (2020) Rhodium(III)-Catalyzed C–H/N–H Alkyne Annulation of Non-Symmetric 2-Aryl-(Benz)Imidazole Derivatives: Photophysical and Mechanistic Insights. Journal of Organic Chemistry, 86 (1). pp. 264-278. ISSN 0022-3263. (doi:10.1021/acs.joc.0c02054) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided) (KAR id:98532)

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Official URL: https://doi.org/10.1021/acs.joc.0c02054

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.

Item Type:	Article
DOI/Identification number:	10.1021/acs.joc.0c02054
Divisions:	Divisions > Division of Natural Sciences > Chemistry and Forensics
Funders:	National Council for Scientific and Technological Development (https://ror.org/03swz6y49) Coordenação de Aperfeicoamento de Pessoal de Nível Superior (https://ror.org/00x0ma614) Alexander von Humboldt Foundation (https://ror.org/012kf4317) Royal Society of Chemistry (https://ror.org/025sbr097)
Depositing User:	Felipe Fantuzzi
Date Deposited:	30 Nov 2022 15:09 UTC
Last Modified:	06 Dec 2022 15:22 UTC
Resource URI:	https://kar.kent.ac.uk/id/eprint/98532 (The current URI for this page, for reference purposes)
Dias, Gleiston G.:	https://orcid.org/0000-0003-4952-756X
Sabino, Adão A.:	https://orcid.org/0000-0003-1265-7694
Cury, Luiz A.:	https://orcid.org/0000-0002-0763-4431
Fantuzzi, Felipe:	https://orcid.org/0000-0002-8200-8262
da Silva Júnior, Eufrânio N.:	https://orcid.org/0000-0003-1281-5453

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