Exploring New Parameter Spaces for the Oxidative Homocoupling of Aniline Derivatives: Sustainable Synthesis of Azobenzenes in a Flow System

Autor: Ferenc Fülöp, Ádám Georgiádes, Sándor B. Ötvös
Rok vydání: 2015
Předmět:
Zdroj: ACS Sustainable Chemistry & Engineering. 3:3388-3397
ISSN: 2168-0485
DOI: 10.1021/acssuschemeng.5b01096
Popis: Aromatic azo compounds have countless applications, not merely in the chemical industry, but also in medicinal chemistry, biotechnology, and the field of renewable resources. However, in the synthetic batch routine, the synthesis of azobenzenes often constitutes a significant challenge, mainly because of the ease of overreaction leading to nonoptimal selectivity, and also because of reactivity issues necessitating long reaction times and special reaction conditions. We therefore exploited the benefits of continuous-flow processing for the copper-mediated oxidative homocoupling of arylamines to facilitate the time-, cost-, and atom-effective synthesis of azobenzenes. The novel process window of increased temperature and pressure ranges in combination with the application of overheated solvents afforded a remarkable chemical intensification. Precise control of the residence time restricted the possibility of undesired reaction pathways, such as overreaction to azoxy products, but at the same time ensured su...
Databáze: OpenAIRE