Direct photochemical route to azoxybenzenes via nitroarene homocoupling. Issue 36 (8th September 2022)

• Record Type: Journal Article
• Authors: Yaghoubian, Ali; Hodgson, Gregory K.; Adler, Marc J.; Impellizzeri, Stefania
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 36(2022)
• Page Start: 7332
• Page End: 7337
• Publication Date: 2022-09-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01247b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Ultraviolet illumination of nitrobenzenes at 365 nm produces their azoxy counterparts through a direct photochemical route. Abstract : We report on a direct photochemical method for the one-pot, catalyst- and additive-free synthesis of azoxybenzene and substituted azoxy derivatives from nitrobenzene building blocks. This reaction is conducted at room temperature and under air, and can be applied to substrates with a wide range of substituents. Yields of products derived from para - and meta -substituted nitrobenzenes are typically good, while sterically encumbered ortho -substituted substrates are not as fruitful. Photochemical Wallach rearrangement of generated azoxybenzenes to ortho -hydroxyazoxybenzenes was observed in some cases, most markedly in selected ortho -halogenated nitrobenzenes. Overall, this method provides an efficient, green pathway to highly value-added azoxybenzene products.