Sodium hydroxide-catalyzed transfer hydrogenation of carbonyl compounds and nitroarenes using ethanol or isopropanol as both solvent and hydrogen donor

• Published in: Journal of molecular catalysis. A, Chemical Vol. 400; pp. 14 - 21
• Main Authors: Wang, Dong, Deraedt, Christophe, Ruiz, Jaime, Astruc, Didier
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.05.2015
• Subjects: Carbonyl; Catalysis; Ethanol; Nitroarene; Sodium hydroxide; Transfer hydrogenation; Transfer hydrogenation; Nitroarene; Catalysis; Ethanol; Carbonyl; Sodium hydroxide
• ISSN: 1381-1169; 1873-314X
• DOI: 10.1016/j.molcata.2015.01.024

[Display omitted] •Sodium hydroxide catalyze aryl ketone hydrogenation in ethanol at 80°C.•Sodium hydroxide reduces nitroarene to azoxyarene and azoarene in alcohols.•Selectivity in nitroarene reduction is strongly dependent on the alcohol structure. The development of a clean and renewable energy carrier has become a subject of high priority, and new catalytic system that involves both abundant and cheap catalysts and green solvents is highly desirable in terms of practical and sustainable chemistry. In this spirit, sodium hydroxide-catalyzed transfer hydrogenation of carbonyl compounds using ethanol as both hydrogen source and solvent is developed in this report. The process is successfully utilized in the hydrogenation of various ketones and aldehydes, and the corresponding primary and secondary alcohols are synthesized with excellent conversions. Furthermore, sodium hydroxide also smoothly promotes the transfer hydrogenation of nitroarenes providing anilines and azobenzenes. For both carbonyl compounds and nitroarenes, results in ethanol and isopropanol are compared, and a remarkable change of selectivity between these two solvents is disclosed for the NaOH-catalyzed transfer hydrogenation to nitroarenes.