Combination of Aryl Diselenides/Hydrogen Peroxide and Carbon‐Nanotube/Rhodium Nanohybrids for Naphthol Oxidation: An Efficient Route towards Trypanocidal Quinones

• Published in: Chemistry : a European journal Vol. 24; no. 57; pp. 15227 - 15235
• Main Authors: de Carvalho, Renato L., Jardim, Guilherme A. M., Santos, Augusto C. C., Araujo, Maria H., Oliveira, Willian X. C., Bombaça, Ana Cristina S., Menna‐Barreto, Rubem F. S., Gopi, Elumalai, Gravel, Edmond, Doris, Eric, da Silva Júnior, Eufrânio N.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 12.10.2018; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Subjects: Aromatic compounds; Carbon; carbon nanotubes; Chagas disease; Chemical Sciences; Chemistry; Chemistry, Multidisciplinary; Hydrogen peroxide; Nanotubes; Naphthol; Oxidation; Physical Sciences; Quinones; Rhodium; rhodium nanohybrid; Science & Technology; Selenides; selenium; CANCER-CELLS; Chagas disease; oxidation; BETA-LAPACHONE; CYCLOADDITION; carbon nanotubes; selenium; PHENOLS; rhodium nanohybrid; CATALYTIC-OXIDATION; quinones; HYDROGEN-PEROXIDE; HYDROQUINONE; DERIVATIVES; BENZENESELENINIC ACID; ANHYDRIDE
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201802773

This work reports a combination of aryl diselenides/hydrogen peroxide and carbon‐nanotube (CNT)/rhodium nanohybrids (RhCNT) for naphthol oxidation towards the synthesis of 1,4‐naphthoquinones and evaluation of their relevant trypanocidal activity. Under a combination of (PhSe)2/H2O2 in the presence of O2 in iPrOH/hexane, several benzenoid (A‐ring)‐substituted quinones were prepared in moderate to high yields. We also studied the contribution of RhCNT as co‐catalyst in this process and, in some cases, yields were improved. This method provides an efficient and versatile alternative for preparing A‐ring‐modified naphthoquinonoid compounds with relevant biological profile. It's the mix that makes it! A combination of aryl diselenides/hydrogen peroxide for naphthol oxidation towards synthesis of 1,4‐naphthoquinones and evaluation of their relevant trypanocidal activity. Under a combination of PhSeSePh/H2O2 in the presence of O2 in iPrOH/Hexane, several substituted benzenoid quinones were prepared in moderate to high yields. RhCNT was also used as co‐catalyst in this process.