2244-88-4

Upstream product

• 288-88-0 1,2,4-Triazole 
• 3076-56-0 p-tolyllead triacetate 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 106-43-4 para-chlorotoluene 
• 352-32-9 p-fluorotoluene 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 539-44-6 N-4-methylphenylhydrazine 
• 17873-01-7 (4-methylphenyl)trimethoxysilane 

Downstream Products

• 1538612-41-7 1-(4-methyl-3,5-dinitrophenyl)-1H-1,2,4-triazole 
• 1538612-39-3 1-(4-methyl-3-nitrophenyl)-1H-1,2,4-triazole 

Relevant academic research and scientific papers

Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis

Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.

A Multicomponent Electrosynthesis of 1,5-Disubstituted and 1-Aryl 1,2,4-Triazoles

A novel electrochemical route has been developed for the synthesis of 1,5-disubstituted and 1-aryl 1,2,4-triazoles from aryl hydrazines, paraformaldehyde, NH4OAc, and alcohols. In this multicomponent reaction system, alcohols act as solvents as well as reactants and NH4OAc is used as the nitrogen source. With the assistance of reactive iodide radical or I2 and NH3 electrogenerated in situ, this process could effectively avoid the use of strong oxidants and transition-metal catalysts and be smoothly carried out at room temperature to give a wide array of 1,2,4-triazole derivatives in good to high yields. Preliminary studies reveal that the reaction mechanism involves a radical process.

The Catalytic Properties of a Copper-Based Nanoscale Coordination Polymer Fabricated by a Solvent-Etching Top-Down Route

Manipulating particle size is a powerful means of creating unprecedented applications in both inorganic and organic materials. Coordination polymers, which are emerging as a type of organic–inorganic hybrid materials, have attracted thriving interest in a variety of applications, but nanoscale coordination polymers have scarcely been touched. In this work, the pure-phase {Cu6[1,4-bis(imidazol-1-yl)butane]3I6}∞ coordination polymer with different sizes and morphologies was synthesized for the first time through a facile top-down route assisted by solvent etching. The size and morphology could be adjusted simply by varying the participating etching solvents. Our mechanistic investigations suggest that the bulk coordination polymer as a precursor in the etching solvents may experience a process of dispersion, dissolution, and recrystallization to generate the nanoscale counterpart. High catalytic activity of the nanoscale coordination polymer was observed in the N-arylation of imidazole aryl halides, and this was attributed to a high surface area and a low coordination number of unsaturated coordination sites. This simple and rapid preparation, requiring neither specialized equipment nor harsh conditions, suggests a wealth of potential for reducing the size of coordination polymers to comply with various practical applications.

Efficient and recyclable copper-based MOF-catalyzed N-arylation of N-containing heterocycles with aryliodides

Copper-based MOF-199 was used as an efficient heterogeneous catalyst to catalyze cross-coupling reactions between N-containing heterocycles and aryliodides with high yields. The catalyst can be easily separated from the reaction mixture, and can be reused at least 5 times without significantly decreasing the activity. The XRD results showed that the crystallinity and structure of MOF-199 can be maintained well during the coupling reaction.

Highly active recyclable heterogeneous Pd/ZnO nanoparticle catalyst: Sustainable developments for the C-O and C-N bond cross-coupling reactions of aryl halides under ligand-free conditions

Efficient Pd supported on ZnO nanoparticles for the ligand-free O-arylation and N-arylation of phenols and various N-H heterocycles with aryl chlorides, bromides, and iodides were readily synthesized and characterized. The amount of palladium on ZnO is 9.84 wt% (0.005 g of the catalyst contains 462 × 10-8 mol% of Pd) which was determined by ICP analysis. This nano sized Pd/ZnO with an average particle size of 20-25 nm and specific surface area 40.61 m2 g-1 was used as a new reusable heterogeneous catalyst for the formation of C-O and C-N bonds in organic synthesis. This protocol gives the arylated product in satisfactory yields without any N2 or Ar flow. The catalyst can be recovered and recycled several times without marked loss of activity.

Triazole-substituted nitroarene derivatives: Synthesis, characterization, and energetic studies

A series of dense and energetic polynitroaryl-1,2,4-triazoles were synthesized through the nitration of aryl-1,2,4-triazoles. The Cu-catalyzed/base-mediated coupling reactions of haloarenes with 1,2,4-triazoles delivered N-aryl-1,2,4-triazoles. These new

Phosphorescent platinum(II) complexes based on C^C* cyclometalating aryltriazol-5-ylidenes

Two series of heteroleptic platinum(II) carbene compexes of the type [Pt(C^C)(O^O)] (O^O = acetylacetonate) with C^C* cyclometalated 4-phenyl-1,2,4-triazol-5-ylidene as well as 1-phenyl-1,2,4-triazol-5-ylidene ligands were prepared. The effect of various

Highly efficient ci￡n bond forming reactions in water catalyzed by copper(i) iodide with calix[4]arene supported amino acid ionic liquid

A novel and effective protocol has been developed for the Ullmann-type Ci￡N coupling reaction catalyzed by calix[4]arene supported amino acid ionic liquid and copper(I) iodide in water under microwave irradiation condition. The protocol uses calix[4]arene supported amino acid ionic liquid as double function of the ligand and phase-transfer catalyst, and shows good tolerance in good to excellent yields. A novel and effective protocol has been developed for the Ullmann-type Ci￡N coupling reaction catalyzed by calix[4]arene supported amino acid ionic liquid and copper(I) iodide in water under microwave irradiation condition. The protocol uses calix[4]arene supported amino acid ionic liquid as double function of the ligand and phase-transfer catalyst, and shows good tolerance in good to excellent yields. Copyright

Efficient iron/copper cocatalyzed N-arylation of arylamines with bromoarenes

Fe(acac)3 and Cu(OAc)2H2O were found to effectively promote the C-N cross-coupling reaction in the presence of K 2CO3 as the base. A series of diaryl amine with different substituents can be synthesized in moderate to good yields. This efficient and economic method is attractive for applications on an industrial scale. Georg Thieme Verlag Stuttgart - New York.

An effective N-ligand for copper-catalyzed N-arylation of triazole

An effective N-ligand for copper-catalyzed N-arylation of 1H-1,2,4- triazole has been developed. In the presence of Cu2O, Cs 2CO3, N-ligand-B, 1H-1,2,4-triazole were coupled with toluene to afford the corresponding product