4171-34-0

Upstream product

• 586-96-9 Nitrosobenzene 
• 591-19-5 m-Bromoaniline 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 1227476-15-4 Azobenzene 
• 585-79-5 m-nitrobromobenzene 
• 98-95-3 nitrobenzene 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 62-53-3 aniline 
• 591-19-5 m-Bromoaniline 
• 37790-18-4 (E)-1-(3-bromophenyl)-2-phenyldiazene 

Relevant academic research and scientific papers

TEMPO catalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

A metal-free direct oxidative dehydrogenation approach for the synthesis of azobenzenes from hydrazobenzenes has been developed by using TEMPO as an organocatalyst for the first time. The reaction proceeded in open air under mild reaction conditions. A wide range of hydrazobenzenes readily undergo dehydrogenation to give the corresponding azobenzenes in excellent yields.

Photocatalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

Visible light mediated oxidative dehydrogenation of hydrazobenzenes under an ambient atmosphere using an organic dye as a photocatalyst was reported for the first time. The reaction provides an environmentally benign method for the preparation of azobenzenes in excellent yields with good functional group tolerance.

Photocatalysis Enabling Acceptorless Dehydrogenation of Diaryl Hydrazines at Room Temperature

Aromatic azo compounds are privileged structural motifs, and they exhibit a myriad of pharmaceutical as well as industrial applications. Here, we report a catalytic acceptorless dehydrogenation of diarylhydrazine derivatives to access a wide variety of aryl-azo compounds with the removal of molecular hydrogen as the sole byproduct. This distinctive reactivity has been achieved under dual catalytic conditions by merging the visible-light active [Ru(bpy)3]2+ as the photoredox catalyst and Co(dmgH)2(py)Cl as the proton-reduction catalyst. The reaction proceeds smoothly under very mild and benign conditions and operates at ambient temperature. This dual catalytic approach is highly compatible with many different functional groups and has a broad substrate scope. We have also demonstrated the reversible hydrogen storage and release phenomenon on hydrazobenzene/azobenzene couple to show the utility of these compounds as hydrogen storage materials. Further diversification of azobenzene was shown by a transition-metal-catalyzed azo-group-directed ortho-C-H bond functionalization.

Dehydrogenation of the NH?NH Bond Triggered by Potassium tert-Butoxide in Liquid Ammonia

A novel strategy for the dehydrogenation of the NH?NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH3) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one-pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.

Palladium-Catalyzed Carbonylative Cyclization of Azoarenes

In this communication, we established an interesting palladium-catalyzed carbonylation protocol for the intramolecular cyclization of azoarenes. With Mo(CO)6 as the solid CO source and through C(sp2)?H bond activation, a series of azoarenes were transformed into the corresponding 2-arylindazolones in moderate to good yields. Notably, not only symmetrical azoarenes, but also unsymmetrical substrates underwent the reaction with excellent regioselectivity.

Deoxygenative coupling of nitroarenes for the synthesis of aromatic azo compounds with CO using supported gold catalysts

A facile and efficient catalytic system based on a mesostructured ceria-supported gold (Au/meso-CeO2) catalyst was developed for the synthesis of various aromatic azo compounds by the reductive coupling of the corresponding nitroaromatics, using CO as the sole deoxygenative reagent, under additive-free and mild reaction conditions.

Gold-catalyzed direct hydrogenative coupling of nitroarenes to synthesize aromatic azo compounds

The azo linkage is a prominent chemical motif which has found numerous applications in materials science, pharmaceuticals, and agrochemicals. Described herein is a sustainable heterogeneous-gold-catalyzed synthesis of azo arenes. Available nitroarenes are deoxygenated and linked selectively by the formation of N-N bonds using molecular H2 without any external additives. As a result of a unique and remarkable synergy between the metal and support, a facile surface-mediated condensation of nitroso and hydroxylamine intermediates is enabled, and the desired transformation proceeds in a highly selective manner under mild reaction conditions. The protocol tolerates a large variety of functional groups and offers a general and versatile method for the environmentally friendly synthesis of symmetric or asymmetric aromatic azo compounds.

Preparation of diazenes by electrophile C-coupling reactions of dry arenediazonium o-benzenedisulfonimides with Grignard reagents

The diaryldiazenes (19 examples) and aryl(tertbutyl)diazenes (3 examples) 3 were prepared by electrophilic C-coupling reactions of dry arenediazonium o-benzenedisulfonimides 1 with Grignard reagents. The reactions were carried out in anhyd THF at -78°C un