18440-53-4

Upstream product

• 620-84-8 4-methyldiphenylamine 
• 99-99-0 1-methyl-4-nitrobenzene 
• 5720-05-8 4-methylphenylboronic acid 
• 62-53-3 aniline 

Downstream Products

• 129533-52-4 5,10-di(4-tolyl)-5,10-dihydrophenazine 
• 620-84-8 4-methyldiphenylamine 

Relevant academic research and scientific papers

Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids

The synthesis of diarylamine is extremely important in organic chemistry. Herein, a novel electrochemical reductive arylation of nitroarenes with arylboronic acids was developed. A variety of diarylamines were synthesized without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell and several derivatization reactions were carried out smoothly. Cyclic voltammetry experiments and mechanism studies showed that acetonitrile, formic acid, and triethyl phosphite all played a role in promoting this reductive arylation transformation.

Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst

We report an efficient method for the oxidative dehydrogenation of hydrazines and diarylamines in aqueous ethanol using Anderson-type polyoxomolybdate-based iron(iii) as a catalyst and hydrogen peroxide as an oxidant. A series of azo compounds and tetraarylhydrazines were obtained in moderate to excellent yields. The reaction conditions and substrate scopes are complementary or superior to those of more established protocols. In addition, the catalyst shows good stability and reusability in water. The preliminary mechanistic studies suggest that a radical process is involved in the reaction.

Tunable Electrochemical C?N versus N?N Bond Formation of Nitrogen-Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications

Herein, an environmentally friendly electrochemical approach is reported that takes advantage of the captodative effect and delocalization effect to generate nitrogen-centered radicals (NCRs). By changing the reaction parameters of the electrode material and feedstock solubility, dearomatization enabled a selective dehydrogenative C?N versus N?N bond formation reaction. Hence, pyrido[1,2-a]benzimidazole and tetraarylhydrazine frameworks were prepared through a sustainable transition-metal- and exogenous oxidant-free strategy with broad generality. Bioactivity assays demonstrated that pyrido[1,2-a]benzimidazoles displayed antimicrobial activity and cytotoxicity against human cancer cells. Compound 21 exhibited good photochemical properties with a large Stokes shift (approximately 130 nm) and was successfully applied to subcellular imaging. A preliminary mechanism investigation and density functional theory (DFT) calculations revealed the possible reaction pathway.

Transition-Metal-Free Dehydrogenative N–N Coupling of Secondary Amines with KI/KIO4

A transition-metal-free method for the dehydrogenative N–N coupling of secondary amines has been accomplished. This oxidative KI/KIO4 protocol is mild and operationally simple. A diverse range of diphenylamines, carbazoles, and N-alkylanilines readily undergo N–N homo-coupling effectively. Notably, the N–N cross-coupling of two different arylamines is also demonstrated, which provides a straightforward approach to the complex N–N structures.

Facile Cu(I)-catalyzed oxidative coupling of anilines to azo compounds and hydrazines with diaziridinone under mild conditions

A mild and highly efficient Cu(I)-catalyzed oxidative coupling of anilines is described. Various primary and secondary anilines can be efficiently coupled under mild conditions to the corresponding azo compounds and hydrazines in high yields. This method provides a direct and practical access to these compounds and is also amenable to gram scale with no special precautions to exclude air or moisture.

Fast synthesis of hydrazine and Azo derivatives by oxidation of rare-earth-metal-nitrogen bonds

A novel N-N coupling reaction was developed through the oxidation of rare-earth-metal-nitrogen bonds produced by treatment of the easily available rare-earth-metal amides [(Me3Si)2N]3RE(μ-Cl) Li(THF)3 with aromatic primary or secondary amines. The reaction provides the symmetrical or unsymmetrical azo compounds and hydrazine derivatives in good to high yields within a very short time under mild conditions.