18250-08-3

Upstream product

• 100-52-7 benzaldehyde 
• 106-40-1 4-bromo-aniline 
• 2101-88-4 1-azido-4-bromobenzene 
• 621-82-9 Cinnamic acid 
• 20320-17-6 1-(4-bromophenyl)-1H-1,2,3-triazole 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 1198463-78-3 (Z)-3-((4-bromophenyl)amino)-1,3-diphenylprop-2-en-1-one 
• 6286-30-2 anti-3-phenyl-2,3-dibromopropanoic acids 
• 780-20-1 N-benzylidene-4-bromoaniline 
• 10480-35-0 1-(4-bromophenyl)-4,5-dihydro-5-phenyl-1H-1,2,3-triazole 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Transition-metal-free regioselective construction of 1,5-diaryl-1,2,3-triazoles through dehydrative cycloaddition of alcohols with aryl azides mediated by SO2F2

A novel, simple and practical method for mild, efficient, cost-effective and regioselective synthesis of highly valuable 1,5-diaryl-1,2,3-triazoles was achieved through dehydrative annulation of readily available alcohols with aryl azides. The reaction proceeded at room temperature, without any metal catalysts, exhibiting excellent compatibility to a large variety of functional groups (>50 examples), resulting in up to quantitative yields. 2019

Copper-catalyzed decarboxylative regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles

A copper-catalyzed decarboxylative regioselective protocol for the synthesis of 1,5-disubstituted 1,2,3-triazoles through direct annulation of cinnamic acids with aryl azides has been developed. This is the first example of 1,5-disubstituted 1,2,3-triazoles, under aerobic conditions using Cu(ii) as the catalyst, which were generally synthesized using a ruthenium(ii) catalyst. The simplicity and regioselectivity of this methodology, complementing to the classical CuAAC catalyzed the synthesis of 1,4-disubstituted 1,2,3-triazoles.

Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts

An effective method for C-5 arylation of 1,4-disubstituted 1,2,3-triazoles and C-5 regioselective arylation of 1-substituted 1,2,3-triazoles via sp 2 C-H activation with palladium as a catalyst and diaryliodonium salts as arylating reagents is described. Various electron-rich and electron-deficient substituents attached to triazoles and diaryliodonium salts were tolerable to give the desired products with good isolated yields in 24 hours under air atmosphere.

Base-mediated reaction of vinyl bromides with aryl azides: One-pot synthesis of 1,5-disubstituted 1,2,3-triazoles

A one-pot base-mediated reaction of azides and β- or α-vinyl bromides has been reported. The effects of bases and solvents have been investigated in the process. A variety of 1,5-disubstituted triazoles were prepared in low to good yields. Further studies reveal that the corresponding alkynes were produced as intermediates via elimination reaction. Under the same reaction conditions, the reactions of alkyl alkynes with phenyl azide would give 1,5-disubstituted 1,2,3-triazoles.

A metal-free multicomponent cascade reaction for the regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles

About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α-amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see scheme, Ts=4-toluenesulfonyl).

Sodium hydride-mediated synthesis of 1,5-diaryl-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and organic azides

A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide. The reaction is mild and simple, does not require a transition-metal catalyst, and gives products in good to excellent yields.

Lewis acid mediated fragmentation of tetrazoles towards triazoles

If Ugi-azide adducts generated from tert-butyl isocyanide, primary amines, and aromatic aldehydes are oxidized by copper(II) salts, the resulting imino tetrazoles may be easily converted into triazoles through Lewis acid catalyzed fragmentation of the tet

Potassium tert-butoxide promoted cycloaddition reaction for the synthesis of 1,5-disubstituted 1,2,3-triazoles from aromatic azides and trimethylsilyl-protected alkynes

The cycloaddition reaction of aromatic azides and trimethylsilyl alkynes upon treatment with desilylating reagents was investigated. In the process, the use of t-BuOK in wet DMF generated 1,5-disubstituted 1,2,3-triazoles regioselectively in moderate to g

Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited

After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles.

Triazolines 24. Permanganate-Catalyzed Low Temperature Thermolysis of 5-(4-Pyridyl) Substituted 1,2,3-Triazolines

Potassium permanganate oxidation of 1-aryl-5-(4-pyridyl)-1,2,3-triazolines I in a benzene-water two-phase system using the phase-transfer catalyst tetrabutylammonium chloride yields the corresponding 1H-1,2,3-triazoles II.However, when the reaction is run