Copper-catalyzed N-arylation Reaction Research Articles

Copper catalysis the synthesis of functionalized glycine-based sulphonamides: In silico and in vitro antibacterial studies

The synthesis of functionalized glycine-based sulphonamides via copper catalyzed N-arylation reaction and the in silico, in vitro antibacterial studies is reported. The procedure involved the initial synthesis of substituted p-toluenesulphonamides and substituted benzenesulphonamides by the reaction of glycine with p-toluenesulphonyl chloride and benzenesulphonyl chloride respectively in aqueous basic medium. The syn[1]thesized compounds were acetylated by reacting them with acetic anhydride and sodium acetate followed by acylation and amidation to yield amidated p-toluenesulphonamides and benzenesulphonamides respectively. Copper catalyzed N-arylation of the amidated products with aryltriolborates resulted in the synthesis of benzene, and 2-chlorophenyl derivatives of the amidated products. The synthesized compounds were characterized using FTIR, 1HNMR and elemental analysis and the spectra were in agreement with the assigned structures. The in silico antibacterial studies revealed that the compounds possess significant antibacterial potency in the respective bacteria cells and could be further employed as potential anti-bacterial agents. The in vitro antimicrobial study revealed that most of the synthesized compounds possess antibacterial activities.

Chemospecific and ligand free CuI catalysed heterogeneous N-arylation of amines with diheteroaryl halides at room temperature

A ligand free, copper-catalyzed N-arylation reaction of amines with diheteroaryl halides in heterogeneous medium at room temperature has been developed. The protocol is very effective for low boiling amines and useful for amines available in aqueous solution. The reaction gives chemospecific arylation of amines with diheteroaryl halides in the mixture monoheteroaryl halides, diheteroaryl halides and carbocyclic aryl halides. The reaction is also chemospecific with respect to arylation of aliphatic amines. Monoarylated piperazines were also synthesized at room temperature following this protocol.

Facile Access to a Variety of 2,5-Biaryl-1,2,4-triazol-3-ones via Regioselective N-Arylation of Triazolones

A selective synthetic method of the 2,5-biaryltriazolones has been developed via copper-catalyzed N-arylation reaction. Aryltriazolones, which were readily prepared from commercially available compounds, were N-arylated to 2,5-biaryltriazolones with high regioselectivity. This approach allows for access to a variety of 2,5-biaryl-1,2,4-trizol-3-ones in a simple and practical manner.

ChemInform Abstract: Copper‐Catalyzed N‐Arylation Reaction of 2‐Azabicyclo[2.2.1]hept‐5‐en‐3‐one with Arylboronic Acids under Microwave Irradiation.

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Dendritic Structure Having a Potential Gradient: New Synthesis and Properties of Carbazole Dendrimers

A new synthetic route for carbazole dendrimers was discovered using the copper-catalyzed N-arylation reaction. This synthetic route allowed synthesizing the fourth generation carbazole dendrimer and several derivatives for the first time. The crystal structure, Mark-Houwink-Sakurada plots, and UV-vis and fluorescence studies showed that the dendritic carbazole backbone has a rigid and highly twisted structure. From the measurement of the redox potential of the ferrocene derivatives, the IR spectra of the benzophenone derivatives, and complexation behavior of the phenylazomethine derivatives, the inductive electron-withdrawing effect of the carbazole dendron was revealed. This suggested that the summation of this electron withdrawal from each layer may produce a potential gradient such that the outer layer is electron-rich and the inner layer is electron-poor in the carbazole dendron. By assignment of the (1)H and (13)C NMR spectra of the dendron, the existence of this kind of potential gradient was proved. Overall, these data show the pi-polarization substituent effect of the carbazole unit, and their summation determines the potential gradient in the repeating dendritic structure of the carbazole dendrimer.

Copper-Catalyzed N-Arylation Reaction of 2-Azabicyclo[2.2.1]hept-5-en-3-one with Arylboronic Acids under Microwave Irradiation

Copper-catalyzed N-arylation reaction of 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) with arylboronic acids was successively performed in the presence of KOH and trimethylamine-N-oxide under microwave irradiation.

The Synthesis of Heterocycles Using Cascade Chemistry

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New DNA Intercalating Acridinic Ligands: Comparative Copper-Catalyzed N-Arylation Reactions of 4-Aminoacridine with Organobismuth, Organoboron and Organolead Compounds

Copper diacetate catalyzed phenylation of 4-aminoacridine afforded the N-phenyl derivative in good yields with triphenylbismuth diacetate, moderate yields with phenylboronic acid and failed with in situ generated phenyllead triacetate. All systems gave high yields of the N-monophenyl derivative in their reaction with 3,4-dimethylaniline. Keywords: aminoacridine, copper catalysis, organobismuth, organoboron, organolead