Direct photochemical route to azoxybenzenes <i>via</i> nitroarene homocoupling

Yaghoubian, Ali; Hodgson, Gregory K.; Adler, Marc J.; Impellizzeri, Stefania

doi:10.1039/d2ob01247b

Cited by 3 publications

(2 citation statements)

References 54 publications

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“…Soon later, Impellizzeri and co‐workers [22] discovered that by employing 365 nm ultraviolet light to excite nitrobenzene in i ‐PrOH solvent, they could obtain azoxybenzenes 6 instead of aniline products 4 (Scheme 4). This methodology exhibits a wide substrate scope.…”

Section: The Reduction Of Nitroarenementioning

confidence: 99%

The application of nitroarenes in catalyst‐free photo‐driven reactions

Teng,

Liu,

et al. 2024

ChemPhotoChem

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Nitroarenes are usually excited to form photoexcited species in light‐induced reactions due to their unique properties, leading to the development of numerous related catalyst‐free photo‐induced reactions encompassing diverse reaction types and key intermediates. This review aims to summarize the progress in catalyst‐free photo‐induced reactions involving photoexcited nitroarenes and offers a brief overview of future directions in this field.

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Section: The Reduction Of Nitroarenementioning

confidence: 99%

The application of nitroarenes in catalyst‐free photo‐driven reactions

Teng,

Liu,

et al. 2024

ChemPhotoChem

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“…Among azo compounds, aromatic azo compounds have a higher π electron conjugation system along with higher chemical stability and thermal stability. Moreover, the substituents on the aromatic ring have a direct impact on their properties, which promoted the design of functional photoresponsive materials at the molecular level [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 ]. As a result, the research and application of aromatic azo compounds have received great attention and undergone significant development in the past ten years, as shown in Figure 1 .…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Aromatic Azo Compounds

Zhao,

Tang,

Han

2023

Molecules

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Aromatic azo compounds have -N=N- double bonds as well as a larger π electron conjugation system, which endows aromatic azo compounds with wide applications in the fields of functional materials. The properties of aromatic azo compounds are closely related to the substituents on their aromatic rings. However, traditional synthesis methods, such as the coupling of diazo salts, have a significant limitation with respect to the structural design of aromatic azo compounds. Therefore, many scientists have devoted their efforts to developing new synthetic methods. Moreover, recent advances in the synthesis of aromatic azo compounds have led to improvements in the design and preparation of light-response materials at the molecular level. This review summarizes the important synthetic progress of aromatic azo compounds in recent years, with an emphasis on the pioneering contribution of functional nanomaterials to the field.

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Sustainable and Environmentally Friendly Approach for the Synthesis of Azoxybenzenes from the Reductive Dimerization of Nitrosobenzenes and the Oxidation of Anilines

Karakaya,

Mart,

Altundas

2024

ACS Omega

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This study demonstrates a comparative synthesis of azoxybenzenes through the reductive dimerization of nitrosobenzenes and the oxidation of anilines. Utilizing the cost-effective DIPEA catalyst at room temperature with water as a green solvent, the one-pot procedure involves in situ generation of nitrosobenzene derivatives from anilines in the presence of oxone, followed by DIPEA addition. Both methods yield azoxybenzenes with high selectivity, showcasing the versatility of DIPEA in facilitating the synthesis of azoxybenzenes with various substituents in ortho, meta, and para positions, encompassing electrondonating and electron-withdrawing groups. The use of DIPEA proves pivotal in achieving moderate to high yields, emphasizing its significance in this environmentally friendly synthesis.

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Direct photochemical route to azoxybenzenes via nitroarene homocoupling

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...

Cited by 3 publications

References 54 publications

The application of nitroarenes in catalyst‐free photo‐driven reactions

The application of nitroarenes in catalyst‐free photo‐driven reactions

Recent Advances in the Synthesis of Aromatic Azo Compounds

Sustainable and Environmentally Friendly Approach for the Synthesis of Azoxybenzenes from the Reductive Dimerization of Nitrosobenzenes and the Oxidation of Anilines

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