Sustainable and Environmentally Friendly Approach for the Synthesis of Azoxybenzenes from the Reductive Dimerization of Nitrosobenzenes and the Oxidation of Anilines

Abstract

This study demonstrates a comparative synthesis of azoxybenzenes through the reductive dimerization of nitrosobenzenes and the oxidation of anilines. Utilizing the cost-effective DIPEA catalyst at room temperature with water as a green solvent, the one-pot procedure involves in situ generation of nitrosobenzene derivatives from anilines in the presence of oxone, followed by DIPEA addition. Both methods yield azoxybenzenes with high selectivity, showcasing the versatility of DIPEA in facilitating the synthesis of azoxybenzenes with various substituents in ortho, meta, and para positions, encompassing electron-donating and electron-withdrawing groups. The use of DIPEA proves pivotal in achieving moderate to high yields, emphasizing its significance in this environmentally friendly synthesis.