332-06-9

Upstream product

• 332-07-0 bis-(4-fluorophenyl)diazene 
• 326-04-5 N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide 
• 332-07-0 (E)-bis(4-fluorophenyl)diazene 
• 371-40-4 4-fluoroaniline 
• 73183-34-3 bis(pinacol)diborane 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 332-07-0 (E)-bis(4-fluorophenyl)diazene 
• 137182-59-3 1-acetyl-1,2-bis(4-fluorophenyl)hydrazine 
• 137182-60-6 1,2-bis(4-fluorophenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one 
• 332-07-0 bis-(4-fluorophenyl)diazene 
• 16858-27-8 1,2-bis-(4-fluoro-phenyl)-pyrazolidine-3,5-dione 
• 326-04-5 1,2-bis(4-fluorophenyl)diazene oxide 
• 371-40-4 4-fluoroaniline 

Relevant academic research and scientific papers

Visible-Light-Promoted Diboron-Mediated Transfer Hydrogenation of Azobenzenes to Hydrazobenzenes

A visible-light-promoted transfer hydrogenation of azobenzenes has been developed. In the presence of B2pin2 and upon visible-light irradiation, the reactions proceeded smoothly in methanol at ambient temperature. The azobenzenes with diverse functional groups have been reduced to the corresponding hydrazobenzenes with a yield of up to 96%. Preliminary mechanistic studies indicated that the hydrogen atom comes from the solvent and the transformation is achieved through a radical pathway.

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

Convenient semihydrogenation of azoarenes to hydrazoarenes using H2

The high atom-economical and eco-benign nature of hydrogenation reactions make them much more superior to conventional reduction and transfer hydrogenation. Herein, a convenient and highly selective hydrogenation reaction of azoarenes using molecular hydrogen to access diverse hydrazoarenes is reported. The present catalytic method is general and operationally simple, and it operates under exceedingly mild conditions (room temperature and 1 atm of hydrogen pressure). The reusability of catalysts used in this method is also successfully demonstrated.

Method for preparing 4, 4'-disubstituted-2, 2'-diaminodiphenyl and hydrochloride thereof through reductive coupling

The invention discloses a method for preparing 4, 4'-disubstituted-2, 2'-diaminodiphenyl and hydrochloride thereof based on 4-substituted nitrobenzene and through reductive coupling. The method comprises the following steps: in the presence of an organic

Synthesis of novel 1,2-diarylpyrazolidin-3-one–based compounds and their evaluation as broad spectrum antibacterial agents

There is a continuous need to develop new antibacterial agents with non-traditional mechanisms to combat the nonstop emerging resistance to most of the antibiotics used in clinical settings. We identified novel pyrazolidinone derivatives as antibacterial hits in an in-house library screening and synthesized several derivatives in order to improve the potency and increase the polarity of the discovered hit compounds. The oxime derivative 24 exhibited promising antibacterial activity against E. coli TolC, B. subtilis and S. aureus with MIC values of 4, 10 and 20 μg/mL, respectively. The new lead compound 24 was found to exhibit a weak dual inhibitory activity against both the E. coli MurA and MurB enzymes with IC50 values of 88.1 and 79.5 μM, respectively, which could partially explain its antibacterial effect. A comparison with the previously reported, structurally related pyrazolidinediones suggested that the oxime functionality at position 4 enhanced the activity against MurA and recovered the activity against the MurB enzyme. Compound 24 can serve as a lead for further development of novel and safe antibiotics with potential broad spectrum activity.

Transfer Hydrogenation of Azo Compounds with Ammonia Borane Using a Simple Acyclic Phosphite Precatalyst

Tris(quinolin-8-yl)phosphite, P(Oquin)3, promotes the dehydrogenation of H3N·BH3 (AB) and the transfer hydrogenation of azoarenes using ammonia borane (AB) as H2 source. The metal-free reduction of azoarenes proceeds under mild reaction conditions upon which several diphenylhydrazine derivatives are obtained in high yields. The reactivity of P(Oquin)3 toward AB was evaluated through NMR in situ tests. The rate of the reaction, activation parameters, deuterium kinetic isotope effect (DKIE) and linear-free energy relationship were investigated. Such mechanistic and kinetic studies suggest that P(Oquin)3 is a precatalyst and that AB is likely involved in more than one stage of the reaction pathway. Furthermore, the kinetic data indicate that the reaction proceeds through an ordered transition state, possibly associative.

A switchable-selectivity multiple-interface Ni-WC hybrid catalyst for efficient nitroarene reduction

Selective reduction of nitroarenes is extremely valuable in industrial chemical production. The main reduced products are usually aniline derivatives obtained using single-component noble- or transition-metal catalysts; however, other important products such as hydrazobenzene derivatives always involve in harsh conditions and multiple reaction steps. Here, we realize an unexpected switchable reduction of nitroarenes into aniline or hydrazobenzene derivatives with high yield and selectivity just by controlling the molar ratio of nitroarenes to N2H4·H2O with a nickel–tungsten carbide composite nanocatalyst loaded on carbon (Ni-WC/C). A series of control experiments and density functional theory (DFT) calculations indicate that the multiple interfaces between Ni and WC can induce a synergistic effect, significantly modulating the electronic structure of the Ni-WC/C catalyst, and endowing the catalyst with switchable selectivity and high activity for the reduction of nitroarenes by hydrogenation. This synergistic multi-interfacial catalyst may offer a new way to design and explore highly efficient and selective catalysts for the controllable reduction of nitroarenes and similar hydrogenation reactions.

Electrochemical dehydrogenation of hydrazines to azo compounds

A strategy for the electrochemical dehydrogenation of hydrazine compounds is disclosed under ambient conditions. This protocol proceeded smoothly in ethanol by employing electrons as clean oxidants. Its synthetic value is well demonstrated by the highly efficient synthesis of symmetric and unsymmetric azo compounds. It is an environmentally friendly transformation and the present protocol was effective on a large scale.

Bi(I)-Catalyzed Transfer-Hydrogenation with Ammonia-Borane

A catalytic transfer-hydrogenation utilizing a well-defined Bi(I) complex as catalyst and ammonia-borane as transfer agent has been developed. This transformation represents a unique example of low-valent pnictogen catalysis cycling between oxidation states I and III, and proved useful for the hydrogenation of azoarenes and the partial reduction of nitroarenes. Interestingly, the bismuthinidene catalyst performs well in the presence of low-valent transition-metal sensitive functional groups and presents orthogonal reactivity compared to analogous phosphorus-based catalysis. Mechanistic investigations suggest the intermediacy of an elusive bismuthine species, which is proposed to be responsible for the hydrogenation and the formation of hydrogen.