Continuous flow synthesis of azobenzenes via Baeyer–Mills reaction

    • Jan H. Griwatza,b
    • Anne Kunza,b
    • Hermann A. Wegnera,b
    • aInstitute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany
    • bCenter for Material Research (ZfM/LaMa), Justus Liebig University, Heinrich-Buff-Ring 16, 35392 Giessen, Germany

    Azobenzene, as one of the most prominent molecular switches, is featured in many applications ranging from photopharmacology to information or energy storage. In order to easily and reproducibly synthesize non-symmetric substituted azobenzenes in an efficient way, especially on a large scale, the commonly used Baeyer–Mills coupling reaction was adopted to a continuous flow setup. The versatility was demonstrated with a scope of 20 substances and the scalability of this method exemplified by the synthesis of >70 g of an azobenzene derivative applied in molecular solar thermal storage (MOST) systems.

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