Porous carbons-derived from vegetal biomass in the synthesis of quinoxalines. Mechanistic insights
We report herein for the first-time acid biomass-derived carbons from vegetal biomass, with high developed porosity, prepared through integrating method comprising pyrolysis and surface phosphonation, able to efficiently catalyze the synthesis of quinoxalines from 1,2-diamines and α-hydroxi ketones,...
| Authors: | , , , , , |
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| Format: | article |
| Publication Date: | 2020 |
| Country: | España |
| Institution: | Universidad Nacional de Educación a Distancia |
| Repository: | e-spacio. Repositorio Institucional de la UNED |
| Language: | English |
| OAI Identifier: | oai:e-spacio.uned.es:20.500.14468/25152 |
| Online Access: | https://hdl.handle.net/20.500.14468/25152 |
| Access Level: | Open access |
| Keyword: | 23 Química Porous carbons nanocatalysts fine chemicals quinoxalines computational methods |
| Summary: | We report herein for the first-time acid biomass-derived carbons from vegetal biomass, with high developed porosity, prepared through integrating method comprising pyrolysis and surface phosphonation, able to efficiently catalyze the synthesis of quinoxalines from 1,2-diamines and α-hydroxi ketones, under aerobic conditions. The obtained results indicate that the reaction is mainly driven by a combination of acid function strength and textural properties in terms of conversion and selectivity. Furthermore, our experimental and theoretical observations suggest that the preferred reaction pathway for this transformation, in the presence of the investigated acid carbon catalysts, involves cascade reactions including imination reaction between reactants, successive imine-enamine and keto-enol tautomerisms, heterocyclization followed by dehydration, and aromatization. While the acid sites seem to be a relevant role in each reaction step, the system formed by activated carbon and molecular oxygen could be behind the last oxidative reaction to give the corresponding nitrogen heterocycles. |
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