Mechanistic Study of Oxidative Aromatization Using Activated Carbon–Molecular Oxygen System in the Synthesis of 2-Arylbenzazoles: Focus on the Role of Activated Carbon

Abstract

Abstract Nineteen activated carbons, including sixteen tailor-made and three commercially available ones, were employed to investigate their role in the one-pot synthesis of 2-arylbenzazoles starting from 2-aminophenol, 1,2-diaminobenzene, or 2-aminobenzenethiol, and aldehyde via oxidative cyclization of intermediate phenolic Schiff base promoted by the activated carbon–molecular oxygen system. Tailor-made activated carbons were prepared from wood, coconut shell, and coal by the steam activation method or the chemical activation method. All activated carbons were characterized to clarify their properties, such as metal contaminants, specific surface area, porosity, and surface functionality. After examining their effects on reactivity in the oxidative aromatization, we found that the essential role of activated carbon in this oxidation system is concerned not with metal contaminants, specific surface area, pore volume, mean pore diameter, and surface oxygen groups evolving as CO2 at 900 °C but with surface oxygen groups evolving as CO during heating at 900 °C, such as carbonyl groups on the surface of activated carbon. Additionally, in the synthesis of 2-arylbenzoxazole, it was found that activated carbon would also promote the cyclization of the intermediate Schiff base.