Three-component Click Reaction Research Articles

Post-synthetic modification of Zr-based metal organic framework by schiff base zinc complex for catalytic applications in a click reaction

A novel nanocatalyst, denoted as UiO-66/Sal-ZnCl2, has been synthesized and systematically characterized employing a range of analytical techniques, including Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), thermogravimetric analysis (TGA), Brunauer–Emmett–Teller (BET) surface area analysis, and inductively coupled plasma (ICP) analysis. The comprehensive analyses collectively affirm the effective coordination of zinc chloride onto the functionalized UiO-66. Subsequently, the catalytic efficacy of UiO-66/Sal-ZnCl2 was assessed in a one-pot, three-component click reaction involving terminal alkynes, alkyl halides, and sodium azide, conducted in an aqueous medium. The catalyst demonstrated remarkable catalytic activity, showcasing the capability to facilitate the reaction with high yields and exceptional regioselectivity. Noteworthy attributes of this nanocatalyst and the method include its elevated efficiency, recyclability, convenient product workup, and, significantly, the utilization of a sustainable solvent medium. The synthesis, characterization, and catalytic performance of this catalyst collectively contribute to its potential as an innovative and reusable nanocatalyst for diverse synthetic transformations.

Lewis acid-mediated transformations of 5-acyl-N-fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles.

We present a transition metal-free approach to 2-N-substituted indenones, cyclopentenones, and 4-carbonyl oxazoles, based on the reaction of 5-acylated N-fluoroalkyl substituted 1,2,3-triazoles (prepared by a three-component click reaction of copper acetylides, fluoroalkyl azides, and acyl chlorides) with Lewis acids aluminium trichloride or boron trifluoride etherate, proceeding via the generation and cyclization of vinyl cations.

Multicomponent click polymerization for the synthesis of coumarin containing 1,4-polytriazoles and their application as dye adsorbent

The synthesis of heterocycle-based polymers have remained an important area of research in polymer chemistry. Herein we report a one-pot synthesis of a set of novel coumarin containing regioselective 1,4-polytriazols by multicomponent click polymerization using Cs2CO3 as a base and copper(I) acetate as a catalyst in DMF medium. In this one-pot process, O-alkylation followed by a three-component click reaction between the coumarin-linked dialkyne, sodium azide and alkyl/benzyl dibromides provide novel polymers having coumarin-triazole-linker (C-T-L) units. Ten novel polymers have been synthesized with high molecular weights (Mw = 20,080–46,340 g/mol) and very good yields (83–93%). All the polymers were well characterized by IR, NMR, and GPC. The dye removal capacities of these polymers were evaluated for methylene blue (MB), rhodamine B (RB), methyl orange (MO), and congo red (CR). Polymers P1, P2, and P3 showed very high affinity towards methylene blue dye and among them, P2 showed the highest dye removal efficiency (971 mg/g) for MB. The reusability of P2 was checked and found excellent removal efficiency (RE = 96%) up to the eighth cycle.

Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction.

A new monophosphine Cu(I) complex bearing bis(pyrazolyl)methane (L1) (CuIL1PPh3) was synthesized and used as a catalyst for the three-component click reaction from an alkyl halide, sodium azide, and terminal alkyne to furnish 1,4-disubstituted 1,2,3-triazoles in up to 93% yield. The catalyst is highly stable, compatible with oxygen/water, and works with total efficiency under ultrasonic condition. The structure of the complex was studied and confirmed by X-ray crystallography, finding a riveting relationship with its catalytic activity. This sustainable triazoles synthesis is distinguished by its high atom economy, low catalyst loading (up to 0.5 mol %), broad substrate scope, short reaction times, operational simplicity, and an easy gram-scale supply of a functionalized product for subsequent synthetic applications.

Magnetic \u03b3Fe2O3@Sh@Cu2O: an efficient solid-phase catalyst for reducing agent and base-free click synthesis of 1,4-disubstituted-1,2,3-triazoles

A hybrid magnetic material γFe2O3@Sh@cu2O was easily prepared from Shilajit (Sh) decorated Fe3O4 and copper acetate. The prepared magnetic hybrid material was fully characterized using different analysis, including Fourier transform infrared (FT-IR), X-ray diffraction (XRD), inductively coupled plasma (ICP), scanning electron microscopy (SEM), Energy-dispersive X-ray spectroscopy (EDX), X-ray photoelectron spectroscopy (XPS), vibrating sample magnetometer (VSM) thermal gravimetric analysis (TGA) and Brunauer–Emmett–Teller (BET). All these analysis revealed that during coating of Fe3O4@Sh using copper salt (II), synchronized redox sorption of CuII to CuI occurs at the same time as the oxidation of Fe3O4 to γFe2O3. This magnetic catalyst exhibited excellent catalytic activity for regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles via one pot three-component click reaction of sodium azide, terminal alkynes and benzyl halides in the absence of any reducing agent. High yields, short reaction time, high turnover number and frequency (TON = 3.5 * 105 and TOF = 1.0 * 106 h−1 respectively), easy separation, and efficient recycling of the catalyst are the strengths of the present method.

A tunable one-pot three-component synthesis of an125I and Gd-labelled star polymer nanoparticle for hybrid imaging with MRI and nuclear medicine

Bimodal radioiodine/Gd labelled polymeric nanoparticles prepared using a versatile one-step three-component click reaction.

Polystyrene-supported ionic liquid copper complex: A reusable catalyst for one-pot three-component click reaction

Copper(II) complex of 1,2-bis(4-pyridylthio)ethane immobilized on polystyrene was a used as a highly stable, active, reusable and green catalyst for click synthesis of 1,2,3-triazoles via one-pot three-component reaction of organic halides, sodium azide and alkynes. The catalyst was characterized by FT-IR spectroscopy, thermogravimetric analysis, elemental analysis, field emission scanning electron microscopy, energy dispersive X-ray, transmission electron microscopy and elemental analysis. High selectivity, broad diversity of organic halides or α-bromoketones and alkyl/aryl terminal alkynes, and excellent yields of the products were obtained using 0.2mol% of catalyst. This catalytic system also showed excellent activity in the synthesis of bis-1,4-disubsitituted 1,2,3-triazoles. Moreover, the catalyst could be recycled and reused for seven cycles without any decrease in its catalytic activity.

Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles.

A Cu/Pd-catalyzed, three-component click reaction of azide, alkyne, and aryl halide has been developed. By using this Cu/Pd transmetalation relay catalysis, a variety of 1,4,5-trisubstituted 1,2,3-triazoles were quickly assembled in one step in high yields with complete regioselectivity, just like assembling Lego bricks. Notably, different from the well-established CuAAC click reactions only working on terminal alkynes, this reaction offers an alternative solution for the problem of the click reaction of internal alkynes.

Synthesis, Structure and H+/K+‐ATPase Inhibitory Activity of Novel Triazolyl Substituted Tetrahydrobenzofuran Derivatives via One‐pot Three‐component Click Reaction

AbstractEleven triazolyl substituted tetrahydrobenzofuran derivatives were synthesized in high yields as novel H+/K+‐ATPase inhibitor via one‐pot CuI‐catalyzed three‐component click reaction of azide, secondary amine and 3‐bromopropyne under mild conditions in water. Their structures were characterized by NMR, IR, ESI‐MS, elemental analysis and single‐crystal X‐ray diffraction analysis. Most of the target compounds exhibited better H+/K+‐ATPase inhibitory activity than commercial omeprazole with IC50 values less than 15 µmol·L−1. The initial structure‐activity analysis suggested that the triazole substituted by cycloalkyl, aromatic ring or O‐containing side‐chain seemed to be beneficial for enhancing the activity.

Structures of Copper Complexes of the Hybrid [SNS] Ligand of Bis(2-(benzylthio)ethyl)amine and Facile Catalytic Formation of 1-Benzyl-4-phenyl-1H-1,2,3-triazole through Click Reaction

A hybrid ligand, bis(2-(benzylthio)ethyl)amine (SNS), with an amine and two thioether donors reacts with Cu(II) to give mononuclear [CuCl(2)(SNS)] (1), [CuBr(2)(SNS)] (2), [Cu(OTf)(2)(SNS)(OH(2))] (3), and an one-dimensional Cu(I) coordination polymer [Cu(2)I(2)(SNS)](n) (4). All complexes have been characterized by single-crystal X-ray diffraction analysis, and 1-3 were studied by EPR analysis at room temperature. Complexes 1 and 2 are penta-coordinated with a distorted square pyramidal metal supported by a tridentate SNS ligand on the basal plane. Complex 3 shows a tetragonally distorted octahedral sphere with two trans and weakly bonding monodentate triflates. A 12-membered ring in the solid lattice is formed by intermolecular H-bonding among the coordinated triflate and aqua ligands from four neighboring molecules. Complex 4, the only Cu(I) in this series, shows a coordination polymer chain [Cu(4)I(4)](n) comprising tetrahedral Cu(I) centers stitched by the SNS ligand in a unique bridge-chelate mode in the form of a helix. All four complexes are catalytically active at room temperature in a copper-catalyzed azide-alkyne cycloaddition (CuAAA) three-component click reaction of benzyl chloride, sodium azide, and phenylacetylene in an aqueous MeCN mixture to give good isolated yields of 1-benzyl-4-phenyl-1H-1,2,3-triazole, without the use of a base or reducing agent.