Glycoluril: A heterogeneous organocatalyst for oxidation of alcohols and benzylic sp3 carbons

• Published in: Applied catalysis. A, General General, 2018-09, Vol.565, p.127-134
• Main Authors: Patel, Parth, Nandi, Sekhar, Menapara, Tusharkumar, Biradar, Ankush V., Nagarale, Rajaram K., Khan, Noorul H., Kureshy, Rukhsana I.
• Format: Article
• Language: English
• Subjects: Glycoluril; Heterogeneous catalyst; Oxidation reaction; Radical reaction; Solid organocatalyst
• ISSN: 0926-860X; 1873-3875
• DOI: 10.1016/j.apcata.2018.08.005

[Display omitted] •Synthesis of novel organocatalyst “Glycoluril” and utilize for the oxidation of alcohols and benzylic sp3 carbon.•Hydrogen peroxide was used as an environment friendly oxidant.•The catalyst was successfully recycled for >10 times without compromising any catalytic activity.•Best of our knowledge this is the first heterogeneous catalyst for oxidation of alcohols and benzylic sp3 carbon atom. Herein, we report a simple and eco-friendly method for synthesizing a heterogeneous organocatalyst “glycoluril” that can be utilized for the direct oxidation of alcohols and benzylic sp3 carbons to the corresponding carbonyls. The organocatalyst gave excellent conversion and selectivity of the products in an aqueous medium using 50% hydrogen peroxide at 60 °C. Investigation of the reaction mechanism using control reactions, electrochemical experiments, kinetic, and NMR studies indicated that the reaction proceeds via radical pathway assisted by the glycoluril catalyst. Overall, the study demonstrated that our catalyst, used here for the first time as a heterogeneous organocatalyst, is robust, universal, and easily applied to the oxidation of alcohols and benzylic sp3 carbons on the lab scale.