Direct Photochemical Route for Amine- and Catalyst-Free Synthesis of Azoxybenzene and Functional Azoxy Derivatives via Accessible Nitroarene Homocoupling under Ambient Conditions

16 May 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

Nitrobenzene reduction
Azoxybenzene
Nitrobenzene photochemistry
Wallach reaction

Supplementary materials

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Description
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Supplementary Information
Description
Absorption Spectra. 1H NMR, 13C CMR and GC-MS data.
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