Rhodium(III)-Catalyzed C-H/N-H Alkyne Annulation of Nonsymmetric 2-Aryl (Benz)imidazole Derivatives: Photophysical and Mechanistic Insights.

Autor: Dias GG; Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil., Paz ERS; Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil., Kadooca JY; Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil., Sabino AA; Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil., Cury LA; Department of Physics, Institute of Exact Sciences, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil., Torikai K; Department of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan., de Simone CA; Institute of Physics, University of São Paulo, São Carlos, São Paulo 13560-160, Brazil., Fantuzzi F; Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg Am Hubland, 97074 Würzburg, Germany., da Silva Júnior EN; Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Jan 01; Vol. 86 (1), pp. 264-278. Date of Electronic Publication: 2020 Dec 11.
DOI: 10.1021/acs.joc.0c02054
Abstrakt: 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.
Databáze: MEDLINE
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