853052-50-3Relevant articles and documents
A highly active catalyst for huisgen 1, 3-dipolar cycloadditions based on the tris(triazolyl)methanol-Cu(I) structure
Oezcubukcu, Salih,Ozkal, Erhan,Jimeno, Cirll,Pericas, Miquel A.
, p. 4680 - 4683 (2009)
A new trls(1 -benzyl-1H-1, 2, 3-triazol-4-yl)methanol ligand 3 has been prepared by a triple Cu(l)-catalyzed alkyne-azilde 1,3-dipolar cycloaddition (CuAAC). Ligand 3 forms a stable complex with CuCl, which catalyzes the Huisgen 1,3-dipolar cycloaddition
Homogeneous and noncovalent immobilization of NHC-Cu catalyzed azide-alkyne cycloaddition reaction
Zhang, Xiangjie,Wang, Bingyang,Lu, Yanmei,Xia, Chungu,Liu, Jianhua
, (2021/02/26)
A series of new pyrene tagged nitrogen heterocyclic carbene copper (NHC-Cu) molecular complexes were synthesized and characterized by 1H- and 13C-NMR, high resolution ESI-mass spectrometry (HR-MS). The corresponding NHC-Cu complex was immobilized onto the surface of multi-walled carbon nanotubes (MWNTs) by using π-π stacking interaction, the noncovalent immobilization catalytic material MWNTs@NHC-Cu were characterized by FT-IR, XRD, XPS, thermogravimetry (TGA) and TEM. The new NHC-Cu complexes were tested both in the homogeneous phase and once immobilized onto multi-walled carbon nanotubes support for the azide-alkyne cycloaddition reaction. Both were active in the two-component click cycloaddition reaction of terminal alkynes and organic azides and three-component cycloaddition reaction that employs various terminal alkynes, NaN3 and organic halides with the advantage of excellent yields, low catalyst dosage, short reaction time. The MWNTs@NHC-Cu catalyst could be separated from the reaction system at the end of the reaction and reused in another catalytic cycle, but with loss of product yield.
Silica immobilized copper N-heterocyclic carbene: An effective route to 1,2,3-triazoles via azide-alkyne cycloaddition and multicomponent click reaction
Garg, Anirban,Borah, Nobomi,Sultana, Jasmin,Kulshrestha, Akshay,Kumar, Arvind,Sarma, Diganta
, (2021/06/11)
A new silica supported copper N-heterocyclic carbene (Cu-NHC@SiO2) complex is prepared and characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS) analyses. This complex is an efficient and easily retrievable catalyst for 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition reaction as well as one-pot reaction using arylboronic acids. This catalytic system is also suitable for synthesis of 4-aryl-NH-1,2,3-triazoles from diverse benzaldehydes. Further, the catalyst can efficiently be recycled up to fifth cycle for all the three methods of 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition and multi-component reactions.
Synthesis of copper containing polyaniline composites through interfacial polymerisation: An effective catalyst for Click reaction at room temperature
Chetia, Mitali,Konwar, Manashjyoti,Pegu, Biswajit,Konwer, Surajit,Sarma, Diganta
, (2021/02/26)
Polyaniline (PANI) supported Cu (Cu/PANI) catalyst served as an efficient heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles via click chemistry approach. Herein, we have illustrated the development of two copp
A novel route to 1,4-disubstituted-1,2,3-triazoles through metal-free decarboxylative azide-alkene cycloaddition
Rengasamy,Vijayalakshmi,Punitha,Paul Raj,Karthikeyan,Elangovan
supporting information, (2021/10/19)
A collection of 1,4-disubstituted 1,2,3-triazoles was achieved by decarboxylative [3 + 2] cycloaddition of organic azides and cinnamic acids. Metal-free condition, high regioselectivity and easy accessibility of starting materials are the salient attributes of this protocol.
Click reactions catalyzed by Cu(I) complexes supported with dihydrobis(2-mercapto-benzimidazolyl)borate and phosphine ligands
Khalili, Dariush,Evazi, Roya,Neshat, Abdollah,Aboonajmi, Jasem,Osanlou, Farzane
supporting information, (2020/03/10)
Four Cu(I) complexes bearing dihydrobis(2-mercapto-benzimidazolyl)borate and phosphine co-ligands were synthesized and their catalytic activity was investigated in azide-alkyne reactions. These complexes were tested as catalyst system and among them a Cu(
Visible-Light-Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron-Transfer Strategy
Wu, Zheng-Guang,Liao, Xiang-Ji,Yuan, Li,Wang, Yi,Zheng, You-Xuan,Zuo, Jing-Lin,Pan, Yi
, p. 5694 - 5700 (2020/04/24)
Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate a novel strategy for the azide–alkyne cycloaddition reaction that involves a photoredox electron-transfer radical mechanism instead of the traditional metal-catalyzed coordination process. This newly developed photocatalyzed azide–alkyne cycloaddition reaction can be performed under mild conditions at room temperature in the presence of air and visible light and shows good functional group tolerance, excellent atom economy, high yields of up to 99 %, and absolute regioselectivity, affording a variety of 1,4-disubstituted 1,2,3-triazole derivatives, including bioactive molecules and pharmaceuticals. The use of a recyclable photocatalyst, solar energy, and water as solvent makes this photocatalytic system sustainable and environmentally friendly. Moreover, the azide–alkyne cycloaddition reaction could be photocatalyzed in the presence of a metal-free catalyst with excellent regioselectivity, which represents an important development for click chemistry and should find versatile applications in organic synthesis, chemical biology, and materials science.
Synthesis, characterization and catalytic properties of a new binuclear copper(II) complex in the azide–alkyne cycloaddition
Akbar Khandar, Ali,Amini, Mojtaba,Ellern, Arkady,Keith Woo, L.,Sheykhi, Ayda
, (2020/07/21)
A new binuclear copper(II)–oxalate complex containing 2,9-dimethyl-1,10-phenanthroline (dmp), was synthesized via a simple and one-pot reaction. [Cu2(dmp)2(ox)Cl2]·H2O (1) was characterized by single-crystal X-ray crystallography and IR methods. The complex 1 was been used to efficiently catalyze the three-component 1,3-Dipolar cycloaddition CuAAC reaction to produce 1,4-disubstituted 1,2,3‐triazoles in good to excellent yields from aromatic or aliphatic halide, sodium azide, and acetylene in water as a green solvent with low catalyst amount.
Dinuclear Cu(I) Halides with Terphenyl Phosphines: Synthesis, Photophysical Studies, and Catalytic Applications in CuAAC Reactions
Beltrán, álvaro,Gata, Inmaculada,Maya, Celia,Avó, Jo?o,Lima, Jo?o Carlos,Laia, César A. T.,Peloso, Riccardo,Outis, Mani,Nicasio, M. Carmen
supporting information, p. 10894 - 10906 (2020/08/12)
Several dinuclear terphenyl phosphine copper(I) halide complexes of composition [CuX(PR2Ar′)]2 (X = Cl, Br, I; R = hydrocarbyl, Ar′ = 2,6-diarylterphenyl radical), 1-5, have been isolated from the reaction of CuX with 1 equiv of the phosphine ligand. Most
Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand-free click synthesis of diverse 1,2,3-triazoles and tetrazoles
Khalili, Dariush,Rezaee, Meysam
, (2019/09/17)
Magnetic CuFe2O4/g-C3N4 hybrids were synthesized through a facile method and their catalytic performances were evaluated in click chemistry for the first time. The structural and morphological characterization of prepared materials was carried out by different techniques such as X-ray diffraction, high-resolution transmission electron microscopy, field emission scanning electron microscopy, Fourier infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, and N2 adsorption–desorption analysis (Brunauer–Emmett–Teller surface area). The utilization of magnetic CuFe2O4/g-C3N4 enabled superior performance in the one-pot azide–alkyne cycloaddition reaction in water using alkyl halides and epoxides as azide precursors without the need of any additional agents. The present system is broad in scope and especially practical for the synthesis of macrocyclic triazoles and also tetrazoles. In addition, the catalytic system highly fulfills the demands of “green click chemistry” with its convenient conditions, especially easy access to a variety of significant products in low catalyst loading and simple work-up and isolation procedure.
