In-situ Oxidation and Coupling of Anilines towards Unsymmetric Azobenzenes Using Flow Chemistry
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https://doi.org/10.22029/jlupub-19272Abstract
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® 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.Link to publications or other datasets
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ChemSusChem 17, 10 (2024), e202301714