78766-51-5

Upstream product

• 91806-09-6 N¹-(p-tolyl)benzene-1,2-diamine 
• 52753-44-3 (2-nitrophenyl)-p-tolylamine 
• 95-14-7 1,2,3-Benzotriazole 
• 75-09-2 dichloromethane 
• 3076-56-0 p-tolyllead triacetate 
• 1256450-74-4 C₁₃H₁₂ClN₃ 
• 240497-09-0 C₁₃H₁₂IN₃ 
• 106-49-0 p-toluidine 
• 62-53-3 aniline 
• 622-74-2 N-phenyl-N'-p-tolyl-triazene 
• 5720-05-8 4-methylphenylboronic acid 
• 2592-95-2 benzotriazol-1-ol 
• 352-32-9 p-fluorotoluene 
• 583-68-6 2-bromo-p-toluidine 

Downstream Products

• 1444922-93-3 C₃₁H₂₆AuN₃P⁽¹⁺⁾*CF₃O₃S^(1-) 
• 4630-20-0 3-Methyl-9H-carbazole 

Relevant academic research and scientific papers

Synthesis of functionized N-arylbenzotriazoles via palladium catalyzed intramolecular amination

The functionalized benzotriazoles are prepared by palladium catalyzed intramolecular amination of 2-bromodiaryltriazene. By screening the reaction conditions, such as ligand, solvent, base and reaction concentration, the optimal reaction conditions were o

Synthetic method of palladium-catalyzed N -aryl benzotriazole derivative

The invention discloses palladium catalysisNA method for synthesizing - arylbenzotriazole derivatives, comprising the steps of reacting under the presence of a palladium catalyst, a ligand and a base, wherein the bromine-substituted aryltriazene is reacte

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.

Mechanistic investigations on C-H activated dealkylating cyclo-amination reactions of substituted triazenes, formamidines and amidines

Catalytic dealkylating cycloamination reactions of N 1-methylated-N 1,N 3-diarylated triazenes proceed via two subsequent oxidative addition reactions, regioselectivity producing benzotriazoles by C-H and C-Br activation steps. Whereas palladium-based catalysis in the presence of dealkylating reagents and directing phosphane ligands leads to high yields, the homologous metals nickel and platinum as well as other 3d transition metals show only poor catalytic activity in similar procedures. Starting compounds have been widely varied to introduce potentially competing reaction sites and to investigate the reaction mechanism of the catalytic cyclization reactions. Yields of the benzotriazole synthesis strongly depend on the electronic and steric properties of the directing phosphane ligands, the nature of the dealkylating bases and the substitution pattern in 2- A nd 4-position of the aryl groups of the starting triazenes. In order to clarify the role of the catalyst, palladium-based intermediates were identified. Finally, formamidines and bulky amidines were tested in related C-H activated dealkylating cycloamination reactions.

Cu-catalyzed arylation of 1-acyl-1H-1,2,3-Benzotriazoles via C–N activation

An efficient copper-catalyzed arylation reaction of 1-acyl-1H-1,2,3-benzotriazoles with diaryliodonium salts via C–N activation is explored. The reaction is conducted regioselectively to form 1-aryl-1H-1,2,3-benzotriazoles in MeCN at 80 °C in the presence of cesium carbonate. 29 examples are given with the product yield of up to 84%. The probable reaction mechanism is proposed.

The Disappearing Director: The Case of Directed N-Arylation via a Removable Hydroxyl Group

A facile and broadly applicable method for the regiospecific N-arylation of benzotriazoles is reported. Copper-mediated reactions of diverse 1-hydroxy-1H-benzotriazoles with aryl boronic acids lead to 1-aryl-1H-benzotriazole 3-oxides. A N1-OH→N3 prototropy in the 1-hydroxy-1H-benzotriazoles is plausibly the underlying basis, where the tautomer is captured by the boronic acid, leading to C?N (not C?O) bond formation. Because the N?O bond in amine N-oxides and 1-hydroxy-1H-benzotriazoles can be easily reduced by diboron reagents such as (pinB)2 and B2(OH)4, exposure of the 1-aryl-1H-benzotriazole 3-oxides to B2(OH)4 then leads to facile reduction of the N?O bond resulting in diverse, regiospecifically-arylated benzotriazoles. Thus, the N-hydroxyl group in 1-hydroxy-1H-benzotriazoles acts as a disposable arylation director. (Figure presented.).

Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D

The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.

Highly efficient and simple catalytic system for the N-arylation of some hindered aza-heterocycles in water

A highly efficient and simple protocol for the N-arylation of some hindered aza-heterocycles in water has been developed with readily available basic copper carbonate as the catalyst using bis(3,5-dimethyl-1H-pyrazol-1-yl)methane as ligand. This mild catalytic system possesses excellent tolerance for a large variety of functional groups. A total of 11 previously unknown coupling products have been synthesized by this methodology.

Pd-catalyzed C-H activation/C-N bond formation: A new route to 1-aryl-1H-benzotriazoles

A method for the C-H activation of aryl triazene compounds followed by intramolecular amination is described. It involves the use of a catalytic amount of Pd(OAc)2 that efficiently effects the cyclization to provide 1-aryl-1H-benzotriazoles at moderate temperature.

A ligand-free copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes in PEG-water: An expeditious protocol towards regiospecific 1-aryl benzotriazoles

An efficient and highly versatile method for the synthesis of diverse regiospecific 1-arylbenzotriazoles being important medicinal scaffolds, by the copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes of 2-haloaryldiazonium salts in PEG-water has been developed. A very simple reaction protocol, large number of substrate affordability and excellent yields are the main features of this methodology.