55324-08-8

Upstream product

• 536-74-3 phenylacetylene 
• 1680-44-0 5-phenyl-1H-1,2,3-triazole 
• 16717-64-9 1-azidostyrene 
• 65913-20-4 (E)-1,2-diphenylvinyl azide 
• 1680-44-0 4-phenyl-1H-1,2,3-triazole 
• 884866-01-7 1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 
• 122-78-1 phenylacetaldehyde 
• 1432593-46-8 1-[2-(methylthio)-1-phenylethyl]-4-phenyl-1H-1,2,3-triazole 
• 4098-17-3 1-(1-azido-2-iodoethyl)benzene 
• 100-42-5 styrene 

Relevant academic research and scientific papers

N2-selective alkylation of NH-1,2,3-triazoles with vinyl ethers: Via gold catalysis

A new method was developed to synthesize N2-alkyl-substituted 1,2,3-triazoles via gold catalyzed alkylation of vinyl ethers with mono- and unsubstituted NH-1,2,3-triazoles and benzotriazole. A hydrogen bond between the oxygen atom of the vinyl ethers, activated via the gold catalyst, and the NH-1,2,3-triazoles was supposed to be generated, which selectively gave the N2-alkylation products.

Effect of resonance on the clickability of alkenyl azides in the strain-promoted cycloaddition with dibenzo-fused cyclooctynes

The clickabilities of various alkenyl and alkyl azides in the strain-promoted cycloaddition with dibenzo-fused cyclooctynes were investigated. Although alkenyl azides generally exhibited lower clickabilities than those of alkyl azides, a sterically-hindered alkenyl azide showed high reactivity comparable with those of alkyl azides. Theoretical analyses indicated that these unique reactivities are derived from the frontier molecular orbital interactions and distortability of the azido groups.

N 1-Selective alkenylation of 1-sulfonyl-1,2,3-triazoles with alkynes via gold catalysis

A N1-selective alkenylation of 1-sulfonyl-1,2,3-triazoles with alkynes via gold catalysis is reported. N1-Vinyl substituted 1,2,3-triazoles were selectively prepared in up to 92% yield through the sulfonyl group of 1,2,3-triazole der

Organocatalytic Vinyl Azide-Carbonyl [3+2] Cycloaddition: High-Yielding Synthesis of Fully Decorated N-Vinyl-1,2,3-Triazoles

For the first time, an enolate-mediated organocatalytic vinyl azide-carbonyl [3+2] cycloaddition (OrgVACC) of various ketones/aldehydes with vinyl azides is reported. It is an efficient intermolecular reaction with excellent outcomes with reference to rat

Alkenes as azido precursors for the one-pot synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon

A one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalyzed azide-alkyne cycloaddition (CuAAC). High yields of the β-methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the methylsulfanyl group has been demonstrated through a series of synthetic transformations, including direct access to 1-vinyl and 4-monosubstituted triazoles.

Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed huisgen-type cycloaddition under inductive-heating conditions

The multistep flow synthesis of vinyl azides and their application in the synthesis of vinyltriazoles is reported. The synthesis relies on a stable polymer-bound equivalent of iodine azide that serves to carry out 1,2-functionalization of alkenes in a telescope flow protocol. The intermediate 2-iodo azides are subjected to a DBU-mediated polymer-supported elimination step yielding vinyl azides in good yield. The third step involves the formation of vinyl triazoles by a copper-catalyzed Huisgen-"click" cycloaddition. The required heat is generated by electromagnetic induction based on copper. Copper serves both as heatable as well as catalytically active packed-bed material inside the flow reactor.

Highly efficient synthesis of vinyl substituted triazoles by Au(I) catalyzed alkyne activation

Au(I) catalyzed 1,2,3-triazole addition to non-activated alkyne was reported. A large group of substituted NH-1,2,3-triazoles were suitable for this transformation along with both internal and terminal alkynes. The N-1 and N-2 vinyl substituted 1,2,3-tria