13148-78-2Relevant articles and documents
Selectivity in an encapsulated cycloaddition reaction
Chen, Jian,Rebek Jr., Julius
, p. 327 - 329 (2002)
(Equation Presented) A 1,3-dipolar cycloaddition takes place within a reversibly formed, self-assembled capsule. The reaction proceeds through an unsymmetrically loaded encapsulation complex with absolute regioselectivity.
One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides
Feldman, Alina K.,Colasson, Benoit,Fokin, Valery V.
, p. 3897 - 3899 (2004)
(Chemical Equation Presented) 1,4-Disubstituted 1,2,3-triazoles are obtained in excellent yields by a convenient one-pot procedure from a variety of readily available aromatic and aliphatic halides without isolation of potentially unstable organic azide intermediates.
Copper(I)-catalyzed azide-alkyne cycloadditions in microflow: Catalyst activity, high-T operation, and an integrated continuous copper scavenging unit
Varas, Alvaro Carlos,Noel, Timothy,Wang, Qi,Hessel, Volker
, p. 1703 - 1707,5 (2012)
Avoiding the coppers: A continuous-flow synthesis for the Cu I-catalyzed azide-alkyne cycloaddition reaction using [Cu(phenanthroline)(PPh3)2]NO3 as a homogeneous catalyst is developed (up to 92 % isolated yield). Elevated temperatures allow achieving full conversions and using lower catalyst loadings. Residual copper in the triazole compound is efficiently removed via an inline extraction process, employing aqueous EDTA as a copper scavenger. Copyright
Glass wool: a novel support for heterogeneous catalysis
Elhage, Ayda,Wang, Bowen,Marina, Nancy,Marin, M. Luisa,Cruz, Menandro,Lanterna, Anabel E.,Scaiano, Juan C.
, p. 6844 - 6852 (2018)
Heterogeneous catalysis presents significant advantages over homogeneous catalysis such as ease of separation and reuse of the catalyst. Here we show that a very inexpensive, manageable and widely available material-glass wool-can act as a catalyst support for a number of different reactions. Different metal and metal oxide nanoparticles, based on Pd, Co, Cu, Au and Ru, were deposited on glass wool and used as heterogeneous catalysts for a variety of thermal and photochemical organic reactions including reductive de-halogenation of aryl halides, reduction of nitrobenzene, Csp3-Csp3 couplings, N-C heterocycloadditions (click chemistry) and Csp-Csp2 couplings (Sonogashira couplings). The use of glass wool as a catalyst support for important organic reactions, particularly C-C couplings, opens the opportunity to develop economical heterogeneous catalysts with excellent potential for flow photo-chemistry application.
CuO–NiO bimetallic nanoparticles supported on graphitic carbon nitride with enhanced catalytic performance for the synthesis of 1,2,3-triazoles, bis-1,2,3-triazoles, and tetrazoles in parts per million level
Gajurel, Sushmita,Dam, Binoyargha,Bhushan, Mayank,Singh, L. Robindro,Pal, Amarta Kumar
, (2021/12/09)
The unification of CuCl2·2H2O and NiCl2·6H2O with the support of graphitic carbon nitride yielded to form an efficient, synergistic, bimetallic nano-catalyst CuO–NiO@g-C3N4. FT-IR, SEM, TEM
Immobilization of vitamin B1 on the magnetic dialdehyde starch as an efficient carbene-type support for the copper complexation and its catalytic activity examination
Abbaspour, M.,Mohammadi Ziarani, G.,Rafiee, F.
, (2021/11/16)
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.
Copper-Catalyzed Four-Component Cascade Reaction for the Construction of Triazoles Bearing β-Hydroxy Chalcogenides
Wang, Xiang-Xiang,Sun, Bo-Xun,Zhao, Zhi-Wei,Chen, Xin,Xia, Wen-Jin,Shen, Yuehai,Li, Ya-Min
supporting information, p. 165 - 171 (2021/10/19)
A copper-catalyzed four-component cascade reaction for the preparation of triazoles bearing β-hydroxy chalcogenides from terminal alkynes, azides, epoxides, and Se/K2S is reported. The present reaction proceeds under mild conditions, and exhibits a good functional group compatibility. A possible mechanism is proposed. (Figure presented.).
A sustainable approach for efficient one-pot synthesis of 1-aryl 1,2,3-triazoles using copper iodide supported on 3-thionicotinyl-urea-modified magnetic nanoparticles in DES
Mirshafiee, Sogand,Salamatmanesh, Arefe,Heydari, Akbar
, (2021/04/09)
An efficient and retrievable copper(I) catalyst was synthesized by immobilizing of copper iodide on 3-thionicotinyl-urea-modified magnetic nanoparticles and characterized using a variety of analysis techniques. The catalytic activity of these nanoparticle
Synthetic access to ring-expanded N-heterocyclic carbene (Re-NHC) copper complexes and their performance in click chemistry
Bouchet, Damien,Cazin, Catherine S. J.,Hall, Jonathan W.,Mahon, Mary F.,Whittlesey, Michael K.
, p. 1252 - 1261 (2021/05/29)
The facile syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in the Huisgen 1,3-cycloaddition reaction.
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.
