F,O,S-Codoped Graphitic Carbon Nitride as an Efficient Photocatalyst for the Synthesis of Benzoxazoles and Benzimidazoles

Author:

Santiago-Aliste Alberto1ORCID,Sánchez-Hernández Eva1ORCID,Andrés-Juan Celia2,Chamorro-Posada Pedro3ORCID,Antorrena Guillermo4,Martín-Gil Jesús1ORCID,Martín-Ramos Pablo1ORCID

Affiliation:

1. Department of Agricultural and Forestry Engineering, ETSIIAA, Universidad de Valladolid, Avenida de Madrid 44, 34004 Palencia, Spain

2. GIR Asymmetric Synthesis, Universidad de Valladolid, Campus Miguel Delibes, Paseo Belén 7, 47011 Valladolid, Spain

3. Department of Theory of Signal and Communications and Telematic Engineering, ETSIT, Universidad de Valladolid, Paseo de Belén 15, 47011 Valladolid, Spain

4. Laboratorio de Microscopias Avanzadas (LMA), Edificio I+D, Campus Río Ebro, Universidad de Zaragoza, C/Mariano Esquillor s/n, 50018 Zaragoza, Spain

Abstract

Graphitic carbon nitride (g-C3N4) is a metal-free heterogeneous catalyst that has attracted attention because of its good chemical stability, cost-effectiveness, and environmental friendliness. In the work presented herein, F,O,S-codoped carbon nitride was synthesized by heating a mixture of melamine cyanurate and trifluoromethanesulfonic acid at 550 °C for 50 min. The obtained product was characterized by transmission electron microscopy, infrared spectroscopy, X-ray powder diffraction, CHNS elemental analysis, total combustion-ion chromatography, X-ray photoelectron spectroscopy, scanning electron microscopy coupled with energy-dispersive X-ray spectroscopy, and UV-Vis spectroscopy. Results point to an F,O,S-codoped g-C3N4. The material was applied as a photocatalyst for the formation of benzoxazoles and benzimidazoles by condensation–aromatization of 2-aminophenol or 1,2-phenylenediamine with suitable aldehydes (viz. benzaldehyde, 4-chlorobenzaldehyde, 2-naphthaldehyde, 2-hydroxybenzaldehyde, and 2-methoxybenzaldehyde), obtaining yields of up to 90% in 15 min under visible light irradiation, with good selectivity and reusability. Thus, the reported findings suggest that this F,O,S-codoped g-C3N4 may hold promise as a metal-free photocatalyst for the rapid synthesis of 2-arylbenzoxazoles and 2-arylbenzimidazoles.

Funder

Junta de Castilla y León

Publisher

MDPI AG

Subject

Physical and Theoretical Chemistry,Catalysis,General Environmental Science

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