Journal
JOURNAL OF CATALYSIS
Volume 292, Issue -, Pages 118-129Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2012.05.002
Keywords
Cascade process; Quinoxaline; 2-Methylquinoxaline; Au/CeO2; Au/HT; Heterogeneous catalyst; 1,2-Phenylenediamine; Diol; Biomass
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Funding
- Spanish Ministry of Education and Science [CTQ-2011-27550]
- Generalitat Valenciana
- Spanish Ministry of Education and Science
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An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to alpha-hydroxycarbonyl compound. Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product. (C) 2012 Elsevier Inc. All rights reserved.
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