Journal article

Publication year: 2024

Journal: Chemistry-Sustainability-Energy-Materials

Volume number: 17

Issue number: 10

ISSN: 1864-5631

eISSN: 1864-564X

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/cssc.202301714

Publisher: Wiley

Abstract: 

Molecular switches, especially azobenzenes, are used in numerous applications, such as molecular solar thermal storage (MOST) systems and photopharmacology. The Baeyer-Mills reaction of anilines and nitrosobenzenes has been established as an efficient synthetic method for non-symmetric azobenzenes. However, nitrosobenzenes are not stable, depending on their substitution pattern and pose a health risk. An in-situ oxidation of anilines with Oxone (R) was optimized under continuous flow conditions avoiding isolation and contact. The in-situ generated nitrosobenzene derivatives were subjected to a telescoped Baeyer-Mills reaction in flow. That way azobenzenes with a broad substituent spectrum were made accessible.

Azobenzenes are often accessed via the Baeyer-Mills reaction of an aniline with a nitrosobenzene. To minimize the hazards while working with such substances, we herein report an in-situ preparation of a large scope of different nitrosobenzene derivatives. These were used in a telescoped Baeyer-Mills reaction of unsymmetric azobenzenes.+ image

Harvard Citation style: Griwatz, J., Campi, C., Kunz, A. and Wegner, H. (2024) In-situ Oxidation and Coupling of Anilines towards Unsymmetric Azobenzenes Using Flow Chemistry, Chemistry-Sustainability-Energy-Materials, 17(10). https://doi.org/10.1002/cssc.202301714

APA Citation style: Griwatz, J., Campi, C., Kunz, A., & Wegner, H. (2024). In-situ Oxidation and Coupling of Anilines towards Unsymmetric Azobenzenes Using Flow Chemistry. Chemistry-Sustainability-Energy-Materials. 17(10). https://doi.org/10.1002/cssc.202301714