Merging heterogeneous graphitic Carbon Nitride photocatalysis with Cobaloxime catalysis in uphill dehydrogenative synthesis of anilines

Synthesis of substituted anilines upon nucleophilic addition of secondary amines to cyclohexanone derivatives followed by aromatization of the enamine by employing a combination of Ir-polypyridine complex as a photoredox catalyst and cobaloxime as H2-evolution catalyst is developed recently by Leono...

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Detalles Bibliográficos
Autores: Zoltowska, Sonia, Mazzanti, Stefano, Stolfi, Sara, Xu, Jingsan, Huš, Matej, Oberlintner, Ana, Pavlin, Matic, Ghigna, Paolo, Likozar, Blaž, Torelli, Piero, Braglia, Luca, Ravelli, Davide, Fagnoni, Maurizio, Agirrezabal Telleria, Iker, Antonietti, Markus, Giusto, Paolo, Savateev, Oleksandr
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/76139
Acceso en línea:http://hdl.handle.net/10810/76139
Access Level:acceso abierto
Descripción
Sumario:Synthesis of substituted anilines upon nucleophilic addition of secondary amines to cyclohexanone derivatives followed by aromatization of the enamine by employing a combination of Ir-polypyridine complex as a photoredox catalyst and cobaloxime as H2-evolution catalyst is developed recently by Leonori et al. In this work, the homogeneous photoredox catalyst is replaced by a heterogeneous and metal-free mesoporous graphitic carbon nitride (mpg-CN). Substituted aromatic amine and H2 are formed simultaneously. Combination of X-ray spectroscopies reveals charge transfer from cobaloxime to mpg-CN in the dark. Illumination of the catalytic system with visible light induces electron transfer from mpg-CN to cobaloxime and formation of persistent Co(II) species. The results of density functional theory modeling suggest that the studied reaction is strongly endothermic and endergonic. Thus, energy of photons is stored in the reaction products—H2 and the aromatic amine.

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