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Relevant academic research and scientific papers

Preparation of aryl azides of aryl boronic acids and one-pot synthesis of 1,4-diaryl-1,2,3-triazoles by a magnetic cysteine functionalized GO–CuI/II nanocomposite

A mixed CuI/CuIIcatalyst based on magnetic cysteine functionalized graphene oxide (CuI/II@Cys-MGO) was prepared and used for the azidonation reaction of aryl boronic acids and one-pot synthesis of 1,4-diaryl ?1,2,3-triazoles. Aryl azides were obtained in good yields and short reaction times via cross-coupling of aryl boronic acids with sodium azide in the presence of CuII catalytic species in this catalytic system. The azide-alkyne cycloaddition reaction was catalyzed by CuI catalytic species in CuI/II@Cys-MGO nanocomposite.

Palladium-catalyzed selective ortho C–H alkoxylation at 4-aryl of 1, 4-disubstituted 1, 2, 3-triazoles

The ortho- C–H bonds at C(4)-aryl of 1, 4-disubstituted 1, 2, 3-triazoles were regioselectively alkoxylated in good to excellent yields with under the directing of the triazole ring. Some products were found to exhibit strong antifungal capacity to fight against root-rot disease of Panax notoginseng by testing the minimum inhibitory concentration (MIC).

Immobilization of vitamin B1 on the magnetic dialdehyde starch as an efficient carbene-type support for the copper complexation and its catalytic activity examination

Since the starch biopolymer is an available and inexpensive matrix with modifiable functionality and stabilization capability for metal ions, in this report, we oxidized it to dialdehyde form for the further functionalization with vitamin B1 as a green σ-donor and π-acceptor carbene type ligand. Immobilization of vitamin B1 on this biopolymer was done through imine bond formation between NH2 groups of aminopyrimidine segment of vitamin B1 and aldehyde functional groups of starch oxide. Thiazolium heterocycle part in this biomolecule provided a carbene type precursor for the metal complexation. After the magnetization process by using of Fe3O4 nanoparticles that lead to quick and facile magnetic separation and metal catalyst recycling, copper ions immobilized on the magnetic support (5.9 wt% Cu, 0.93 mmol/g). The prepared copper N-heterocyclic carbene complex (Fe3O4@DAS@VB1@CuCl nanocomposite) was characterized by FT-IR, SEM, EDX, XRD, VSM, TGA and ICP-OES analysis and then its catalytic activity investigated in azidonation of arylboronic acids and also one-pot coupling reaction of the synthesized aryl azides with phenylacetylene. 1,4-Diaryl 1,2,3-triazoles were obtained in excellent yields (≥90%) at proper reaction times (30–200 min). The magnetic catalyst was recovered by a magnetic field and reused in azidation reaction up to 7 cycle.

Magnetic AgNPs/Fe3O4@chitosan/PVA nanocatalyst for fast one-pot green synthesis of propargylamine and triazole derivatives

A new green magnetic nanocatalyst was introduced for one-pot fast synthesis of propargylamine and triazole derivatives. Chitosan bio-polymeric chains were functionalized with polyvinyl alcohol (PVA) and then templated with silver nanoparticles (AgNPs) and magnetic Fe3O4to obtain the AgNPs/Fe3O4@chitosan/PVA composite. Spectral and analytical examinations were conducted using X-ray diffraction, Fourier transform-infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometry, and energy-dispersive X-ray spectroscopy for understanding the structural, morphological and physiochemical features of the obtained magnetic nanocomposite and the homogeneous distribution of AgNPs on the surface of nanocomposite with Fe3O4nucleus. The AgNPs/Fe3O4@chitosan/PVA nanocatalyst was used in the synthesis of biologically active compounds such as propargylamine and triazole derivatives through multicomponent A3-coupling and click reactions. The catalyzed products were obtained in high yields under ambient conditions through a low-cost, facile, one-pot, and environmentally friendly protocol. The reusability of the heterogeneous magnetic catalyst was also confirmed up to six cycles without any significant loss in the catalytic activity, as well as easy separation of the catalyst.

Copper nanoparticles doped in wrinkled fibrous nanosilica as an efficient catalyst for the synthesis of 1,4-disubstituted 1,2,3-triazole in aqueous solution

A one-pot, highly efficient procedure was reported for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water as a green solvent using Cu@KCC-1-NH-CS2 as a novel nanoreactor. Different methods such as Fourier transform infrared spectroscop

Method for preparing 1,2,3-triazole compound by heterogeneous copper catalysis in one pot

The invention relates to a method for preparing a 1-aryl-4-substituted-1,2,3-triazole compound shown as a formula (II). The method comprises the following steps: mixing arylboronic acid (1), NaN3, a heterogeneous copper catalyst and solvent water, performing a stirring reaction at 25-60 DEG C for 4-8 hours, performing TLC (thin-layer chromatography) monitoring till the arylboronic acid (1) is completely converted, replacing air in the reaction system by using N2, adding a terminal alkyne (2), performing a reaction at 40-80 DEG C for 6-10 hours under the protection of N2, and performing post-treatment on the reaction solution to obtain a product (II). By adopting the preparation method, Cu-coated SBA-15-PTAA is used as a catalyst, a series of 1-aryl-4-substituted-1,2,3-triazole compounds are prepared through a one-pot Chan-Lam/Click series method without additionally adding a reducing agent, the developed catalytic method is green, safe and economical, the amount of three wastes (wastegas, waste water and industrial residue) is small, the yield of a target product is high, and the substrate application range is wide.

Aqueous bile salt accelerated cascade synthesis of 1,2,3-triazoles from arylboronic acids

A facile, efficient and mild copper catalyzed strategy for cascade synthesis of various 1,4-disubstituted 1,2,3-triazoles from arylboronic acids, sodium azide and alkynes was developed by using aqueous bile salt NaDC solution as an accelerating medium. Lo

Combining ethylenediamine and ionic liquid functionalities within SBA-15: A promising catalytic pair for tandem Cu–AAC reaction

This paper discloses the assembly and characterization of an advanced heterogeneous catalyst formulated as CuI@SBA-15/PrEn/ImPF6. It is based on a mesoporous silica SBA-15 skeleton which bears a supported ethylenediamine/CuI complex and covalently anchored imidazolium/PF6 ionic liquid. This catalyst was successfully applied in tandem methods for triazole synthesis starting from different substrate pairs: aryl halides and aryl acetylenes (method A), arylboronic acids and aryl acetylenes (method B). The CuI@SBA-15/PrEn/ImPF6 catalyst showed high activity (up to 90% yields of triazole products under optimized reaction conditions), high stability and no appreciable leaching of CuI owing to its strong binding via the coordination with PrEn functionality. Therefore, the catalyst can be recycled for several consecutive runs (7–14 cycles) in this new synthetic method. For both methods A and B, specific types of green approaches were developed and the favorable products were produced in high yields.

Copper-γ-cyclodextrin complexes immobilized on hexagonal boron nitride as an efficient catalyst in the multicomponent synthesis of 1,2,3-triazoles

A copper-γ-cyclodextrin complex immobilized on hexagonal boron nitride (h-BN@γ-CD@Cu(OAc)2) has been prepared for the first time. This recoverable and reusable heterogeneous catalyst can be used in the click synthesis of 1,2,3-triazoles via a one-pot three-component reaction of boracic acid, terminal alkynes, and sodium azide at room temperature in water. FT-IR, XRD, SEM, XPS, TG, and ICP-AES techniques were used to characterize the catalyst. In general, this reaction, with the aid of this new catalyst, afforded the corresponding products with good yields and excellent tolerance of the functional groups.

One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes

A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.