- Copper(I)-Catalyzed Interrupted Click Reaction with TMSCF3: Synthesis of 5-Trifluoromethyl 1,2,3-Triazoles
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We herein describe a Cu(I)-catalyzed interrupted click reaction, using (trifluoromethyl)trimethylsilane (TMSCF3) as a nucleophilic CF3 source, to synthesize 5-trifluoromethyl 1,2,3-triazoles in one step from readily available terminal alkynes and azides. The reaction shows complete regioselectivity, broad substrate scope, and good functional group tolerability. The application of the reaction has been demonstrated in the synthesis of a trifluoromethylated analog of antiepileptic drug rufinamide.
- Cheung, Kelvin Pak Shing,Tsui, Gavin Chit
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- Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition
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Tris(2-benzimidazolylmethyl)amines have been found to be superior accelerating ligands for the copper(I)-catalyzed azide-alkyne cycloaddition reaction. Candidates bearing different benzimidazole N-substituents as well as benzothiazole and pyridyl ligand a
- Rodionov, Valentin O.,Presolski, Stanislav I.,Gardinier, Sean,Lim, Yeon-Hee,Finn
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- Cu-Al mixed oxide catalysts for azide-alkyne 1,3-cycloaddition in ethanol-water
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Cu(Al)O mixed oxides, which are obtained by the calcination of Cu-Al layered double hydroxide (LDH), promote the formation of 1,2,3-triazoles from an alkyne-azide cycloaddition reaction (Huisgen-type reaction) with excellent yields using an EtOH-H2O mixture as the solvent under microwave heating. The yield of the reaction is the result of both heterogeneous and homogeneous catalytic processes, as a consequence of capturing Cu(ii) from the material by sodium ascorbate. Although the appropriate reaction conditions were employed (EtOH-H2O, 80 °C, MW, 10 min), the reconstruction of LDH by the so-called memory effect was not observed.
- González-Olvera,Urquiza-Castro,Negrón-Silva,ángeles-Beltrán,Lomas-Romero,Gutiérrez-Carrillo,Lara,Santillan,Morales-Serna
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- Mechanistic insights into copper(I)-catalyzed azide-alkyne cycloadditions using continuous flow conditions
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The copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click chemistry") was studied employing copper-in-charcoal (Cu/C) and a variety of copper metal sources as "heterogeneous" catalysts. The type and pretreatment conditions of the different copper sources on the CuAAC were investigated. In addition, the effect of copper leaching from the catalyst over time and in dependence on the reaction mixture composition was studied by ICP-MS analysis in the continuous flow mode. These investigations confirm a "homogeneous" mechanism and suggest surface layer copper(I) oxide as the catalytically active species in CuAAC chemistry involving zerovalent copper metal.
- Fuchs, Michael,Goessler, Walter,Pilger, Christian,Kappea, C. Oliver
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- Metal-Organic Framework Capillary Microreactor for Application in Click Chemistry
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A Cu/PMA-MIL-101(Cr) metal-organic-framework-coated microreactor has been applied in the 1,3-dipolar cycloaddition of benzyl azide and phenylactetylene (click chemistry). The Cu/PMA-MIL-101(Cr) catalyst was incorporated by using a washcoating method. The
- Truter, Lara A.,Juan-Alca?iz, Jana,Kapteijn, Freek,Nijhuis, Tjeerd A.,Gascon, Jorge,Schouten, Jaap C.
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- Novel ion-binding C3 symmetric tripodal triazoles: Synthesis and characterization
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Novel C3 symmetric tripodal molecules were synthesized from cyclohexane 1,3,5-tricarboxylic acid. Utilizing click and Sonogashira reactions, ion-binding triazole and pyridazin-3(2H)-one units were incorporated to form polydentate ligands for ion complexation. The structures of the novel C 3 symmetric derivatives were extensively characterized by 1H, 13C and 2D NMR techniques along with HRMS and IR. The copper(I)-binding potentials of these ligands were investigated by using them as additives in model copper(I)-catalysed azide-alkyne cycloaddition (CuAAC) reactions. The copper(I) complexation ability of our compound was also proved by different spectroscopic methods, such as mass spectrometry, UV and NMR spectroscopy. Based on the mass spectrometric data all of the C3 symmetric ligands formed 1:1 complex with copper(I) ion. The specific role of C3 symmetric polydentate form in the complexation process was also discussed [Figure not available: see fulltext.]
- Neumajer, Gabor,Toth, Gergo,Beni, Szabolcs,Noszal, Bela
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- A Mechanochemically Triggered "click" Catalyst
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"Click" chemistry represents one of the most powerful approaches for linking molecules in chemistry and materials science. Triggering this reaction by mechanical force would enable site- and stress-specific "click" reactions - a hitherto unreported observation. We introduce the design and realization of a homogeneous Cu catalyst able to activate through mechanical force when attached to suitable polymer chains, acting as a lever to transmit the force to the central catalytic system. Activation of the subsequent copper-catalyzed "click" reaction (CuAAC) is achieved either by ultrasonication or mechanical pressing of a polymeric material, using a fluorogenic dye to detect the activation of the catalyst. Based on an N-heterocyclic copper(I) carbene with attached polymeric chains of different flexibility, the force is transmitted to the central catalyst, thereby activating a CuAAC in solution and in the solid state.
- Michael, Philipp,Binder, Wolfgang H.
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- Synthesis of 1,4-disubstituted 1,2,3-triazoles via a three-component reaction in water in the presence of CuX (X = Cl, I)
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(Chemical Equation Presented) Three-component reaction of alkyl halides, sodium azide and alkynes in water in the presence of CuX (X = Cl, I) afforded 1,4-disubstituted 1,2,3-triazoles in high yields. These reactions do not require any special precautions or existence of a reducing agent. The bistriazoles formed during the reaction can efficiently enhance the catalytic activity of the Cu(I) salts.
- Wang, Zhong-Xia,Zhao, Zhi-Gang
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- Recoverable Cu/SiO2 composite-catalysed click synthesis of 1,2,3-triazoles in water media
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An eco-friendly multicomponent reaction for the synthesis of 1,2,3-triazoles using a recoverable and recyclable Cu/SiO2 composite as the catalyst is reported. The reaction proceeds by mixing the benzyl halide, sodium azide, the alkyne and the catalyst in an aqueous medium to afford the desired products in excellent yields. The heterogeneous catalytic system showed high efficiency, performing the multicomponent Huisgen reaction in a green approach based on recoverability, recyclability and avoidance of waste. Microwave irradiation was also applied, substituting for conventional heating, resulting in excellent yields of the products with a dramatic reduction in the reaction time.
- Radatz, Cátia Schwartz,Soares, Liliana Do Amaral,Vieira, Estéfano Roberto,Alves, Diego,Russowsky, Dennis,Schneider, Paulo Henrique
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- Introducing the 4-Phenyl-1,2,3-Triazole Moiety as a Versatile Scaffold for the Development of Cytotoxic Ruthenium(II) and Osmium(II) Arene Cyclometalates
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Herein we report the synthesis, anticancer potency in vitro, biomolecule interaction, and preliminary mode of action studies of a series of cyclometalated 1,2,3-triazole-derived ruthenium(II) (2a-e) and osmium(II) (3a-e) organometallics of the general for
- Riedl, Christoph A.,Flocke, Lea S.,Hejl, Michaela,Roller, Alexander,Klose, Matthias H. M.,Jakupec, Michael A.,Kandioller, Wolfgang,Keppler, Bernhard K.
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- Synthesis of Chiral Nematic Mesoporous Metal and Metal Oxide Nanocomposites and their Use as Heterogeneous Catalysts
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We report the synthesis of chiral nematic mesoporous metal and metal oxide nanocomposites containing zinc or copper prepared through a vacuum-assisted loading of the metal precursor into a chiral nematic mesoporous silica template followed by high-tempera
- Walters, Christopher M.,Adair, Keegan R.,Hamad, Wadood Y.,MacLachlan, Mark J.
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- In Situ Construction of Three Anion-Dependent Cu(I) Coordination Networks as Promising Heterogeneous Catalysts for Azide-Alkyne "Click" Reactions
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Three Cu(I) coordination networks, namely, {[Cu2(bpz)2(CN)X]·CH3CN}n, (X = Cl, 1; I, 3), {[Cu6(bpz)6(CH3CN)3(CN)3Br]·2OH·14CH3CN}n, (2
- Xu, Zhenghu,Han, Lu-Lu,Zhuang, Gui-Lin,Bai, Jing,Sun, Di
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- Azide–Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
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A highly efficient and environmentally benign protocol for copper-catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New copper(I) complexes bearing NHC ligands decorated with bulky hexafluoroisopropylalk
- Topchiy, Maxim A.,Ageshina, Alexandra A.,Gribanov, Pavel S.,Masoud, Salekh M.,Akmalov, Timur R.,Nefedov, Sergey E.,Osipov, Sergey N.,Nechaev, Mikhail S.,Asachenko, Andrey F.
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- Sonochemical synthesis of 1,4-disubstituted 1,2,3-triazoles in aqueous medium
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An ultrasound-accelerated fast and efficient three-component reaction for the regioselective synthesis of l,4-disubstituted 1,2,3-triazoles using different alkyl and allyl halides, terminal alkynes, and sodium azide in water at room temperature has been developed using CuI as catalyst. Ultrasonication dramatically decreases the reaction times. Copyright Taylor & Francis Group, LLC.
- Sreedhar,Reddy, P. Surendra
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- Regiospecific solid-phase synthesis of substituted 1,2,3-triazoles
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A traceless and regiospecific solid-phase synthesis of substituted 1,2,3-triazoles is developed using polystyrene-sulfonyl hydrazide resin. The chemistry is applicable to combinatorial library synthesis.
- Raghavendra, Makam S.,Lam, Yulin
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- Heterogeneous copper-in-charcoal-catalyzed click chemistry
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(Chemical Equation Presented) Click here for Cu/C: Copper-in-charcoal (Cu/C) is an active catalyst for effecting click reactions between organic azides and 1-alkynes. Rates of cycloaddition are increased dramatically when carried out in the presence of Et
- Lipshutz, Bruce H.,Taft, Benjamin R.
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- Investigation of copper-free alkyne/azide 1,3-dipolar cycloadditions using microwave irradiation
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The prevalence of 1,3-dipolar cycloadditions of azides and alkynes within both biology and chemistry highlights the utility of these reactions. However, the use of a copper catalyst can be prohibitive to some applications. Consequently, we have optimized
- Chatkewitz, Lindsay E.,Halonski, John F.,Padilla, Marshall S.,Young, Douglas D.
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- Copper(II) thioxanthone carboxylate as a photoswitchable photocatalyst for photoinduced click chemistry
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A new efficient copper photocatalyst to photochemically induce the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction without the need for additional ligands is reported. The thioxanthone carboxylate moiety was combined with copper(II) ions b
- Dadashi-Silab, Sajjad,Yagci, Yusuf
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- Convergent synthesis of trifunctional molecules by three sequential azido-type-selective cycloadditions
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A facile strategy for the synthesis of trifunctional molecules involving three sequential selective triazole-forming reactions is proposed. This method exploits three kinds of mechanistically different azido-type-selective cycloadditions. Three different azidophiles could be efficiently connected to a triazido platform molecule with three types of azido groups in a consecutive manner, which rendered a practical trifunctional molecule readily available.
- Yoshida, Suguru,Kanno, Kimiyuki,Kii, Isao,Misawa, Yoshihiro,Hagiwara, Masatoshi,Hosoya, Takamitsu
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- 1,2,3-Triazolylidene ruthenium(ii)(η6-arene) complexes: Synthesis, metallation and reactivity
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Three bis(1,2,3-triazolylidene) silver(i) complexes were synthesized, and the ruthenium complexes ([RCH2N2(NMe)C2Ph)] RuCl2(p-cymene) (R = C6H2Me34a 1, C6H
- Bagh, Bidraha,McKinty, Adam M.,Lough, Alan J.,Stephan, Douglas W.
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- Cu(i) coordination polymers (CPs) as tandem catalysts for three-component sequential click/alkynylation cycloaddition reaction with regiocontrol
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To expand coordination polymers (CPs) as solid catalysts to selectively catalyze the three-component tandem click/alkynylation reaction for their fully substituted triazole skeletons, two Cu(i)-based CPs (CuI-CPs), [CuBr(aas-TPB)]n (
- Guo, Xiaoqing,Huang, Chao,Yang, Haiyan,Shao, Zhichao,Gao, Kuan,Qin, Na,Li, Gaoxiang,Wu, Jie,Hou, Hongwei
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- Copper(I)-chitin biopolymer based: An efficient and recyclable catalyst for click azide–alkyne cycloaddition reactions in water
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The naturally occurring α-chitin biopolymer was employed for the immobilisation of copper(I) ion, resulting into a new bioconjugate complex, namely, Cu(I)-α-chitin (CuI-CHT) with catalytic efficiency in copper-catalysed azide–alkyne cycloaddition reaction
- Bahsis, Lahoucine,Ablouh, El-Houssaine,Hachim, Mouhi Eddine,Anane, Hafid,Taourirte, Moha,Julve, Miguel,Stiriba, Salah-Eddine
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- Fe3O4@ZIF-8: Magnetically recoverable catalysts by loading Fe3O4 nanoparticles inside a zinc imidazolate framework
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A simple methodology for encapsulating ca. 10 nm-sized superparamagnetic Fe3O4 nanoparticles in zeolitic imidazolate frameworks (ZIF-8) crystals was developed. The corresponding Fe3O4@ZIF-8 heterostructured mate
- Schejn, Aleksandra,Mazet, Thomas,Falk, Véronique,Balan, Lavinia,Aranda, Lionel,Medjahdi, Ghouti,Schneider, Rapha?l
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- Copper(I)-Catalyzed Three-Component Click/Persulfuration Cascade: Regioselective Synthesis of Triazole Disulfides
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A copper(I)-catalyzed three-component CuAAC/persulfuration reaction providing rapid access to asymmetric triazole disulfides has been developed. The interrupted click reaction shows broad substrate scope, complete regioselectivity, and excellent functiona
- Wang, Weiguo,Lin, Yunzhi,Ma, Yudao,Tung, Chen-Ho,Xu, Zhenghu
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- Sol-gel entrapped Cu in a silica matrix: An efficient heterogeneous nanocatalyst for Huisgen and Ullmann intramolecular coupling reactions
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A recyclable catalytic system has been developed that comprises an inorganic polymer matrix consisting of non-functionalized silica, which encapsulates copper by direct interaction with the matrix. Cu is fixed to a silica support of nanometric dimensions by physical entrapment within a silica sol-gel matrix. Samples with different Cu loadings were studied in order to maximize and optimize the amount of entrapped Cu within the silica matrix. This entrapment limits the diffusion of the metal to the solution, thus ensuring negligible contamination of the product by the metal while simultaneously providing a stabilizing environment. This robust and versatile heterogeneous catalyst was evaluated in Huisgen and Ullmann intramolecular coupling reactions.
- Diz, Paula,Pernas, Paula,El Maatougui, Abdelaziz,Tubio, Carmen R.,Azuaje, Jhonny,Sotelo, Eddy,Guitián, Francisco,Gil, Alvaro,Coelho, Alberto
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- A novel microfluidic approach for preparing chitosan-silica core-shell hybrid microspheres with controlled structures and their catalytic performance
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A facile microfluidic approach to prepare chitosan-silica core-shell hybrid microspheres with different pore structures has been developed. The hybrid microspheres showed good performance in mechanics and adsorption and are outstanding and green catalyst
- Zhao, Hong,Xu, Jian-Hong,Wang, Tao,Luo, Guang-Sheng
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- Hydrosoluble Cu(i)-DAPTA complexes: Synthesis, characterization, luminescence thermochromism and catalytic activity for microwave-assisted three-component azide-alkyne cycloaddition click reaction
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New hydrosoluble and air-stable Cu(i) halide compounds, viz. [CuX(DAPTA)3] (1) and (2), and [Cu(μ-X)(DAPTA)2]2 (3) and (4) (X = Br or I, in this order), have been prepared by reacting Cu(i) halide (i.e., bromide or iodide)
- Mahmoud, Abdallah G.,Guedes Da Silva, M. Fátima C.,Sokolnicki, Jerzy,Smoleński, Piotr,Pombeiro, Armando J. L.
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- One pot synthesis of aminonaphthoquinone derivatives using Cu(II) immobilized on hyperbranched polyglycerol functionalized graphene oxide as a reusable catalyst under solvent-free conditions
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A new Cu(II) immobilized on hyperbranched polyglycerol (HPG) functionalized graphene oxide catalyst was prepared and characterized by FT-IR, TGA, FE-SEM, XRD, and ICP-OES techniques. This catalyst was used efficiently for the preparation of aminonaphthoquinones via one-pot three-component condensation reaction under solvent-free conditions. The catalyst could be easily recovered and reusable several times without a significant loss of activity, which make this method attractive and in a close agreement with green chemistry.
- Naeimi, Hossein,Zarabi, Maryam Farahnak
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- Efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in ionic liquid/water system
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A copper(I) catalyst in a mixture of the ionic liquid [bmim][BF 4] and water, can effect three-component reaction of halides, sodium azide and alkynes to form 1,4-disubstituted 1,2,3-triazoles in good to high yields. The method is efficient and environmentally friendly.
- Zhao, Ya-Bin,Yan, Ze-Yi,Liang, Yong-Min
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- Site-Selective N-Dealkylation of 1,2,3-Triazolium Salts: A Metal-Free Route to 1,5-Substituted 1,2,3-Triazoles and Related Bistriazoles
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N3-Alkylation of 1-(pivaloyloxymethyl)-1,2,3-triazoles with alkyl triflates carrying latent "click" functionality, followed by a nucleophile-promoted N1-dealkylation of the resulting strongly electrophilic intermediate triazolium salts, provides an efficient route to 1,5-disubstituted 1,2,3-triazoles. The azide and alkyne groups incorporated by N-alkylation can be submitted to further copper-catalyzed azide-alkyne and Huisgen cycloadditions to provide bis(1,2,3-triazoles) with unprecedented 1,5/1,4 substitution patterns.
- Monasterio, Zaira,Irastorza, Aitziber,Miranda, José I.,Aizpurua, Jesus M.
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- DABCO/AcOH Jointly Accelerated Copper(I)-Catalysed Cycloaddition of Azides and Alkynes on Water at Room Temperature
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An expeditious room temperature protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal alkynes and substituted azides has been achieved using the combination of CuSO4-ascorbate/1,4-diazabicyclo[2.2.2]octane/acetic acid. This expeditious protocol is applicable to aryl, alkyl, and sulfonyl azides. Acetic acid accelerates the protonation of cuprated triazole and thus avoids the possible side reactions. Devoid of acetic acid, the reaction pathway alters to the ketinimine route and results in the formation of sulfonamides.
- Sarode, Prashant B.,Bahekar, Sandeep P.,Chandak, Hemant S.
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- Microwave-assisted or Cu-NHC-catalyzed cycloaddition of azido-disubstituted alkynes: Bifurcation of reaction pathways
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Microwave irradiation promoted the intramolecular cycloaddition of 2-azidoacetamides derived from α-chiral propargylic amines, affording 1,4,5-trisubstituted triazoles 4 bearing a chiral aminomethyl side chain at C5. In contrast, for the same substrates 3
- Xia, Yuyu,Chen, Ling-Yan,Lv, Shang,Sun, Zhihua,Wang, Bing
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- Efficient multicomponent synthesis of 1,2,3-triazoles catalyzed by Cu(II) supported on PEI@Fe3O4 MNPs in a water/PEG300 system
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A highly dispersible and magnetically recoverable Cu-PEI@Fe3O4 MNPs catalyst was prepared and success-fully applied in one-pot three-component coupling of terminal alkynes, sodium azide, and alkyl bromides/chlorides in water to give
- Hasanpour, Zeinab,Maleki, Aziz,Hosseini, Morteza,Gorgannezhad, Lena,Nejadshafiee, Vajihe,Ramazani, Ali,Haririan, Ismaeil,Shafiee, Abbas,Khoobi, Mehdi
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- 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
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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
- Anvari, Mahsa,Shadjou, Nasrin
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- Synthesis of 1,2,3-triazolyl-5-diethylphosphonate by domino reaction
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The synthesis of 1,2,3-triazolyl-5-diethylphosphonate was studied by the domino reaction of benzyl azide, phenylacetylene and diethyl phosphite. The effect of the reaction stoichiometry, the atmosphere and the amount of the catalyst were investigated.
- Tripolszky, Anna,Tóth, Emese,Bálint, Erika
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- Nitrogen-doped graphene stabilized copper nanoparticles for Huisgen [3+2] cycloaddition "click" chemistry
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Nitrogen-doped reduced graphene oxide (NRGO) stabilized copper nanoparticles are designed to assist Cu(i)-catalyzed Huisgen [3+2] cycloaddition "click" chemistry (CuAAC). This study demonstrates a robust route for the synthesis of vastly dispersed heterog
- Siva Prasanna Sanka,Balaji,Leterrier, Yves,Pandey, Shyam,Srivastava, Monika,Srivastava, Anurag,Binder, Wolfgang H.,Rana, Sravendra,Michaud, Véronique
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- Copper(I)-Catalyzed Three-Component Click/Alkynylation: One-Pot Synthesis of 5-Alkynyl-1,2,3-triazoles
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A copper(I)-catalyzed tandem CuAAC/alkynylation reaction of various alkynes, organic azides, and bromoalkynes to provide rapid access to 5-alkynyl-1,2,3-triazoles has been developed. The reaction proceeded via a copper-catalyzed alkyne azide cycloaddition
- Wang, Weiguo,Wei, Fang,Ma, Yudao,Tung, Chen-Ho,Xu, Zhenghu
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- CuI-functionalized halloysite nanoclay as an efficient heterogeneous catalyst for promoting click reactions: Combination of experimental and computational chemistry
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Amine-functionalized halloysite nanotubes (HNTs-2?N) were prepared and further modified by introduction of salicylaldehyde and formation of imine functionality (HNTs-2?N-Sal). The latter was subsequently used for immobilization of CuI and formation of CuI@HNTs-2?N-Sal, which could effectively promote click reactions of terminal alkynes, sodium azide and α-haloketones or alkyl halides in aqueous media and under mild reaction conditions to afford 1,2,3-triazoles in relatively short reaction times. Notably, the catalyst could be recycled in up to six reaction runs with negligible loss of catalytic activity and CuI leaching. Also, the geometry of CuI adsorption on the modified HNTs surface was explored by molecular simulation with density functional theory. Furthermore, topographic steric maps of possible coordination modes were obtained using the recently released SambVca2 web application tool. Based on obtained results, a catalytic site with superior performance was suggested.
- Bahri-Laleh, Naeimeh,Sadjadi, Samaheh,Heravi, Majid M.,Malmir, Masoumeh
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- Green methodologies for copper(I)-catalyzed azide-alkyne cycloadditions: A comparative study
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Successful copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions may be achieved by several methods. In this paper, four synthetic protocols were performed for direct comparison of time required for the synthesis, yield, and purity of the 1H-1,
- Trujillo, Marissa,Hull-Crew, Clayton,Outlaw, Andrew,Stewart, Kevin,Taylor, Loren,George, Laura,Duensing, Allison,Tracey, Breanna,Schoffstall, Allen
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- Controlled photorelease of alkynoic acids and their decarboxylative deprotection for copper-catalyzed azide/alkyne cycloaddition
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A controlled photorelease of alkynoic acids from the meso-methyl BODIPY photoremovable protecting group facilitates their subsequent efficient decarboxylation to give terminal alkynes for a CuI-catalyzed azide/alkyne cycloaddition. The quantum efficiencies of the photochemical step and the kinetics of the click reaction step are reported.
- Vohradská, Nikoleta,Sánchez-Carnerero, Esther M.,Pastierik, Tomá?,Mazal, Ctibor,Klán, Petr
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- Dicationic 1,3-Bis(1-methyl-1H-imidazol-3-ium) Propane Copper(I) Dibromate : Novel Heterogeneous Catalyst for 1,3-Dipolar Cycloaddition
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Abstract: We disclose synthesis of a novel dicationic 1,3-bis(1-methyl-1H-imidazol-3-ium) propane copper(I) dibromate [Bis-(MIM)](CuBr2)] and explored its potential as a heterogeneous catalyst in 1,3-dipolar cycloaddition for regioselective synthesis of 1, 4-disubstituted-1,2,3- triazoles in excellent yields in ethanol: water (60:40%) system at 80°C. The noteworthy feature of the protocol includes in situ generation of aryl azides by azotisation of aryl as well as alkyl halides with sodium azide thereby enduring facile 1,3-dipolar cycloaddition with terminal alkynes. Graphical Abstract: [Figure not available: see fulltext.]
- Dige, Nilam C.,Patil, Jayavant D.,Pore, Dattaprasad M.
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- Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)-di-p-tolylstibane with organic azides
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Trisubstituted 5-stibano-1H-1,2,3-triazoles were synthesized in moderate to excellent yields by the Cu-catalyzed [3 + 2] cycloaddition of a ethynylstibane with organic azides in the presence of CuBr (5 mol %) under aerobic conditions. The reaction of 5-st
- Yamada, Mizuki,Matsumura, Mio,Uchida, Yuki,Kawahat, Masatoshi,Murata, Yuki,Kakusawa, Naoki,Yamaguchi, Kentaro,Yasuike, Shuji
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- Synthesis of Polysubstituted Imidazoles and Pyridines via Samarium(III) Triflate-Catalyzed [2+2+1] and [4+2] Annulations of Unactivated Aromatic Alkenes with Azides
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Samarium(III) triflate-catalyzed [2+2+1] and [4+2] annulations have been identified for the preparation of fully substituted imidazoles and 2,3,5-trisubstituted pyridines from the readily available unactivated aromatic alkenes and azidomethyl aromatics. T
- Wang, Yingchun,Li, Jiuling,He, Yan,Xie, Yuyang,Wang, Hengshan,Pan, Yingming
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- Scope and reaction mechanism of an aerobic oxidative alkyne homocoupling catalyzed by a di-copper-substituted silicotungstate
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The di-copper-substituted γ-Keggin-type silicotungstate TBA 4[γ-H2SiW10O36Cu 2(μ-1,1-N3)2] (I, TBA = tetra-n- butylammonium) could act as an efficient reusable homogeneous catalyst for the aerobic oxidative alkyne homocoupling. Various kinds of structurally diverse terminal alkynes including aromatic, heteroaromatic, aliphatic, double bond-containing, silylacetylene, propargylic alcohol, and propargylic amine derivatives could selectively be converted into the corresponding diynes in the presence of I. The catalytic activity of I was much higher than those of the mono-copper-substituted silicotungstate, monomeric copper complexes, and simple copper salts, showing that the di-copper core in I plays an important role in the present alkyne homocoupling. The reaction mechanism involving the formation of the di-copper(II)-alkynyl intermediate, reductive elimination of a diyne, and re-oxidation of reduced copper species by O2 has been proposed.
- Mizuno, Noritaka,Kamata, Keigo,Nakagawa, Yoshinao,Oishi, Takamichi,Yamaguchi, Kazuya
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- Copper-catalyzed decarboxylation/cycloaddition cascade of alkynyl carboxylic acids with azide
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A copper-catalyzed decarboxylation/cycloaddition cascade of alkynyl carboxylic acids with azide has been developed. This reaction exhibits good functional group tolerance and wide substrate scope, provides an efficient way to construct 1,4-disubstituted 1
- Shang, Jia-Qi,Fu, Hong,Li, Yi,Yang, Tao,Gao, Chuanzhu,Li, Ya-Min
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- In situ preparation and characterization of novel CuI-functionalized poly[(methyl methacrylate)-co-maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3-triazoles via click reaction: Experimental and computational chemistry
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A CuI-functionalized poly[(methyl methacrylate)-co-maleimide] (CuI@[PMMA-co-MI]) nanocatalyst was prepared from in situ polymerization and functionalization of poly[(methyl methacrylate)-co-(maleic anhydride)] and well characterized using various techniques. From a computational viewpoint, we assessed two complexation models between copper nanoparticles and [PMMA-co-MI]. In this line, the metal–ligand interaction strength was also studied via density functional theory calculations and frontier molecular orbital analysis. Moreover, for presenting a quantitative description of the electronic features of immobilization of copper nanoparticles on polymeric support, the topological analysis of electron density and its Laplacian was performed through quantum theory of atoms in molecules. Finally, the catalytic activity of CuI@[PMMA-co-MI] as a heterogeneous nanocatalyst was successfully examined in the highly regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction.
- Pourmohammad, Nargess,Heravi, Majid M.,Ahmadi, Shervin,Hosseinnejad, Tayebe
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- Synthesis and in vitro cytotoxicity and antibacterial activity of novel1,2,3-triazol-5-yl-phosphonates
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Novel1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate in respect of the catalyst, the base and the solvent, as well as of the reaction parameters (molar ratio of the starting materials, atmosphere, temperature and reaction time). The method elaborated could be applied to a range of organic azides and dialkyl phosphites, which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity on different cell lines and the antibacterial activity of the synthesized1,2,3-triazol-5-yl-phosphonates was explored. According to the IC50 values determined, only modest antibacterial effect was detected, while some derivatives showed moderate activity against human promyelocytic leukemia HL-60 cells.
- Bálint, Erika,Hackler, László,Kari, Beáta,Puskás, László G.,Szabó, Pál Tamás,Tóth, Emese,Tripolszky, Anna
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- Copper(II)-promoted regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles in water
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A high-yielding synthesis of 1,2,3-triazole with cheaply available Cu(OAc)2 without any additional reducing agents is explored, which provides an exclusive 1,4-regioselectivity at ambient conditions in an environmentally benign solvent - water.
- Reddy, K. Rajender,Rajgopal,Kantam, M. Lakshmi
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- A-21·CuI as a catalyst for Huisgen's reaction: About iodination as a side-reaction
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The polymer-supported catalyst Amberlyst A-21·CuI has found many applications in copper(I)-catalyzed Huisgen's (CuAAC) and other reactions. This catalyst was found to be efficient and reusable for the formation of 1,4-disubstituted 1,2,3-triazoles. It was
- Slimi, Riadh,Kalhor-Monfared, Shiva,Plancq, Baptiste,Girard, Christian
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- Ag-NHC anchored on silica: An efficient ultra-low loading catalyst for regioselective 1,2,3-triazole synthesis
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A silica-supported silver complex, Ag-NHC@SiO2, was prepared by an anchoring coordination technique, which was successfully employed for the click reaction under mild reaction conditions. The protocol offered the remarkable advantages of operat
- Garg, Anirban,Khupse, Nagesh,Bordoloi, Ankur,Sarma, Diganta
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- 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
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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
- Gajurel, Sushmita,Dam, Binoyargha,Bhushan, Mayank,Singh, L. Robindro,Pal, Amarta Kumar
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- Tetranuclear and trinuclear copper(i) pyrazolates as catalysts in copper mediated azide-alkyne cycloadditions (CuAAC)
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Homoleptic, tetranuclear copper(i) pyrazolates {[3,5-(t-Bu)2Pz]Cu}4, {[3-(CF3)-5-(t-Bu)Pz]Cu}4, and {[4-Br-3,5-(i-Pr)2Pz]Cu}4are excellent stand-alone catalysts for azide-alkyne cycloaddition reactions (CuAAC). This work demonstrates that a range of pyrazolates, including those with electron donating and electron-withdrawing groups to sterically demanding substituents on the pyrazolyl backbones, can serve as effective ligand supports on tetranuclear copper catalysts. However, in contrast to the tetramers and also highly fluorinated {[3,5-(CF3)2Pz]Cu}3, trinuclear copper(i) complexes such as {[3,5-(i-Pr)2Pz]Cu}3and {[3-(CF3)-5-(CH3)Pz]Cu}3supported by relatively electron rich pyrazolates display poor catalytic activity in CuAAC. The behavior and degree of aggregation of several of these copper(i) pyrazolates in solution were examined using vapor pressure osmometry. Copper(i) complexes such as {[3,5-(CF3)2Pz]Cu}3and {[3-(CF3)-5-(t-Bu)Pz]Cu}4with electron withdrawing pyrazolates were found to break up in solution to different degrees producing smaller aggregates while those such as {[3,5-(i-Pr)2Pz]Cu}3and {[3,5-(t-Bu)2Pz]Cu}4with electron rich pyrazolates remain intact. In addition, kinetic experiments were performed to understand the unusual activity of tetranuclear copper(i) pyrazolate systems.
- Dias, H. V. R.,Patterson, Monika R.
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supporting information
p. 375 - 383
(2021/12/27)
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- Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air
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We developed a highly regioselective base-induced synthesis of N2-substituted 1,2,3-triazoles from N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. We propose an SN2-like mechanistic pathway to explain the high N2-regioselectivity. The protocol features a broad substrate scope and generates products in good to excellent yields (72–90%).
- Ji, Jian,Guan, Cong,Wei, Qinghua,Chen, Xuwen,Zhao, Yun,Liu, Shunying
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supporting information
p. 132 - 136
(2022/01/04)
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- Copper-Catalyzed Four-Component Cascade Reaction for the Construction of Triazoles Bearing β-Hydroxy Chalcogenides
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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.).
- Wang, Xiang-Xiang,Sun, Bo-Xun,Zhao, Zhi-Wei,Chen, Xin,Xia, Wen-Jin,Shen, Yuehai,Li, Ya-Min
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supporting information
p. 165 - 171
(2021/10/19)
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- Supported NHC-Benzimi@Cu Complex as a Magnetically Separable and Reusable Catalyst for the Multicomponent and Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition
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In this paper, we report a novel magnetically separable silica coated copper nano-magnetite NHC-benzimi@Cu complex as heterogeneous catalyst for the multicomponent click reaction via Huisgen 1,3-dipolar cycloaddition reaction of alkyl or aryl halide, sodi
- Chandane, Wilson,Gajare, Shivanand,Jagdale, Ashutosh,Patil, Sandip,Patil, Suresh,Pawar, Arvind,Rashinkar, Gajanan
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- Melamine-supported nickel oxide nanoparticles as a good alternative to conventional copper catalysts for the regioselective synthesis of triazole derivatives in water
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Nickel oxide nanoparticles supported on melamine as a good alternative to conventional copper catalysts have been prepared and used for the regioselective synthesis of triazole derivatives in water. This catalyst can be reused several times without any si
- Hashemi, Zahra,Albadi, Jalal,Jalali, Mehdi
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p. 5291 - 5302
(2021/08/20)
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- Preparation, characterization and catalytic study of a nano-inorganic composite of CuO/NiO for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles in water
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In this research, a nano-inorganic composite of CuO/NiO is prepared by co-precipitation method as an efficient recyclable nanocatalyst for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles in water. The catalyst was characterized by severa
- Albadi, Jalal,Beni, Zohreh Hashemi,Kiyani, Hamzeh
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- Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles
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The synthesis and catalytic activity of three 1,2,3-triazole-based ionic organic–inorganic hybrids as novel water-soluble catalysts for the efficient preparation of spirooxindole derivatives are described. At first, three different 1,2,3-triazoles were prepared by click reaction. Then, these synthesized compounds were reacted with 1,4-butane sultone to generate novel solid 1,2,3-triazolium-N-butyl sulfonate zwitterions. In the next step, the newly synthesized organic zwitterions were treated with an aqueous solution of phosphotungstic acid to give three novel 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstates as targeted organic–inorganic hybrid catalysts. The prepared catalysts were fully characterized using FTIR, 1H and 13C NMR, XRD, elemental analysis (CHNS), ESI–MS, DSC, and TG techniques. The introduced novel SO3H-functionalized ionic hybrid catalysts have a cationic organic triazolium with phosphotungstate anion and are water-soluble with appropriate thermal stability. Their catalytic activity was explored for the synthesis of spirooxindoles via the three‐component reaction of 1,3‐dicarbonyl compounds, barbituric acid, and isatin derivatives. The synthesis of desired spirooxindole products was performed in acceptable times with excellent yields in the presence of low loading amount of the prepared 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstate catalysts (10?mmol%) in water. Some highlighted superiorities of the introduced organic–inorganic hybrids in comparison with most of the previously reported catalysts are as follows: clean and straightforward preparation, novelty of the catalysts, green conditions, ease of recovery, and reusability up to three repeated runs with no significant decrease in the catalytic stability. Graphical abstract: [Figure not available: see fulltext.]
- Keshavarz, Mosadegh,Parhami, Abolfath,Taib, Layla A.
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- Pyridinyl-triazole ligand systems for highly efficient CuI-catalyzed azide-alkyne cycloaddition
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Pyridinyl-triazole ligand systems (including N2-2-pyridinyl 1,2,3-triazoles and N1/N2-substituted 2-(NH-1,2,3-triazol-4-yl)pyridines) were found to be superior ligands for CuI-catalyzed azide-alkyne cycloaddition (CuAAC) r
- Chen, Yunfeng,Meng, Xianggao,Wang, Ye,Zheng, Lei
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- Silica immobilized copper N-heterocyclic carbene: An effective route to 1,2,3-triazoles via azide-alkyne cycloaddition and multicomponent click reaction
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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.
- Garg, Anirban,Borah, Nobomi,Sultana, Jasmin,Kulshrestha, Akshay,Kumar, Arvind,Sarma, Diganta
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- Construction of Stable Metal–Organic Framework Platforms Embedding N-Heterocyclic Carbene Metal Complexes for Selective Catalysis
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We report a bottom-up approach to immobilize catalysts into MOFs, including copper halides and gold chloride in a predictable manner. Interestingly, the structures of MOFs bearing NHC metal complexes maintained a similar 4-fold interpenetrated cube. They
- Kim, Hyunyong,Kim, Hyunseok,Kim, Kimoon,Lee, Eunsung
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supporting information
p. 18687 - 18697
(2021/12/17)
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- Nano-magnetic-iron Oxides@choline Acetate as a Heterogeneous Catalyst for the Synthesis of 1,2,3-Triazoles
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In this research, four cholines supported on core–shell iron oxides, Fe2O3@MgO@Ch.OAc (choline acetate), Fe2O3@MgO@Ch.OH (choline hydroxide), Fe3O4@Ch.OAc, Fe3O4@Ch.OH, were synthesized. The synthesized catalysts were tested in 1,2,3-triazoles synthesis by the reaction of nitromethane, aldehyde, and benzyl azide in EtOH as a green solvent. Among four synthesized heterogeneous catalysts, the Fe2O3@MgO@ch.OAc showed superior catalytic activity for the reaction and afforded the desired triazoles in good isolated yields under mild reaction conditions. Graphic Abstract: [Figure not available: see fulltext.]
- Heydari, Akbar,Mohammadkhani, Abolfazl
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- Homogeneous and noncovalent immobilization of NHC-Cu catalyzed azide-alkyne cycloaddition reaction
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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.
- Zhang, Xiangjie,Wang, Bingyang,Lu, Yanmei,Xia, Chungu,Liu, Jianhua
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- A new amido-phosphane as ligand for copper and silver complexes. Synthesis, characterization and catalytic application for azide-alkyne cycloaddition in glycerol
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The new sterically hindered amido-phosphane 1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-3,7-diylbis(phenylmethanone), DBPTA (1), has been obtained via an open-cage double N-acylation of 1,3,5-triaza-7-phosphadamantane (PTA) using benzoic anhydride. DBPTA i
- Guedes Da Silva, M. Fátima C.,Mahmoud, Abdallah G.,Pombeiro, Armando J. L.
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p. 6109 - 6125
(2021/05/19)
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- Magnetic AgNPs/Fe3O4@chitosan/PVA nanocatalyst for fast one-pot green synthesis of propargylamine and triazole derivatives
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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.
- Amini, Abbas,Cheng, Chun,Darroudi, Mahdieh,Ghasemi, Kousar,Gupta, Anju R.,Rahimi, Marjan,Rouh, Hossein
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supporting information
p. 16119 - 16130
(2021/09/22)
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- Redox Instability of Copper(II) Complexes of a Triazine-Based PNP Pincer
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The new Cu(I) complex [Cu(PNPNTPh-Ph)Cl] (1) containing the tridentate PNP pincer ligand N,N′-bis(diphenylphosphino)-2,6-diamino-4-phenyl-1,3,5-triazine was obtained from the reaction of [Cu(SMe2)Cl]n with the ligand as ether solvate 1.0.5Et2O. 1 was independently obtained from a reaction mixture containing the ligand and the Cu(II) precursor CuCl2.2H2O in 50 % yield alongside with the Cu(II) coordination polymer [Cu(O2PPh2)2]n (2). From the reaction of Cu(NO3)2 ? 3H2O with PNPNTPh-Ph in the presence of pyridine the complexes [Cu(O2PPh2)2(Py)2(H2O)] (3), [Cu(O2PPh2)(Py)2(NO3)]2 (4), and [Cu(Py)4(NO3)2].Py (5), were obtained, 2, 3, and 4 contain diphenyl-phosphinate ligands. The underlying redox reaction of the ligand and Cu(II) yielding the oxidised ligands observed in the by-products and the Cu(I) product complex was further studied using electrochemistry and UV-vis spectroelectrochemistry. Attempts to synthesise the Cu(II) complex [Cu(PNPNTPh-Ph)(NO3)2] (6) in a mechanochemical experiment gave evidence for this unprecedented species from ESI-MS(+) and EPR spectroscopy but also revealed its very high sensitivity to air and moisture. The catalytic activity of 1 was investigated in the azide-alkyne cycloaddition yielding various 1-benzyl-4-phenyl-1H-1,2,3-triazoles. The environmentally benign (“green”) and cheap EtOH/H2O solvent mixture turned out to be very suitable. Melting points, FT-IR, and NMR spectra of the triazole products were analysed.
- Mohammadnezhad, Gholamhossein,Amirian, Ali Mohammad,G?rls, Helmar,Plass, Winfried,Sandleben, Aaron,Sch?fer, Sascha,Klein, Axel
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p. 1140 - 1151
(2021/03/08)
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- CuSO4 nanoparticles loaded on carboxymethylcelulose/polyaniline composites: A highly efficient catalyst with enhanced catalytic activity in the synthesis of propargylamines, benzofurans, and 1,2,3-triazoles
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A novel and efficient heterogeneous CuSO4 nanoparticles (CuSO4 NPs) immobilized on carboxymethylcellulose/polyaniline (CuSO4NPs@CMC/PANI) composites were prepared via one-pot and one-step interfacial oxidative polymerizati
- Xu, Zhian,Xu, Jinxi,Li, Yiqun
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- vvComplexation of copper ion-containing immobilized ionic liquid in designed hierarchical-functionalized layered double hydroxide nanoreactor for azide–alkyne cycloaddition reaction
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A novel nanoreactor containing Cu (II) ions which are well distributed throughout the ionic liquid-based designed layered double hydroxide is applied for azide–alkyne cycloaddition reaction. The synthesized nanocatalyst was fully characterized by thermogravimetry analysis, scanning electron microscopy, X-ray powder diffraction, Fourier transform infrared spectroscopy and Brunauer–Emmett–Teller analysis. The high surface area and the appropriate pore size of the synthesized-nanocatalyst make metal active centers accessible. On the other hand, the presence of ionic liquid in the inner layer of designed hierarchical-functionalized layered double hydroxide nanostructure creates a good environment for the leaching protection and stabilization of extremely dispersed copper ion-containing that results in good reusable features of the nanocatalyst for the synthesis of 1,4-disubstituted-1,2,3-triazole derivatives with excellent yields (75–96%) through an azide-alkyne [3 + 2] cycloaddition reaction.
- Afzali, Elham,Akbarzadeh, Azim,Mirjafary, Zohreh,Saeidian, Hamid
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- Copper-catalyzed: In situ oxidative-coupling for one-pot synthesis of 5-aryl-1,4-disubstituted 1,2,3-triazoles under mild conditions
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A new reaction system with CuCl as catalyst, TEA as base and O2/chloramine-T as oxidant was developed for one-pot in situ oxidative-coupling to synthesize 5-aryl-1,4-disubstituted 1,2,3-triazoles in this paper. A variety of 5-arylated-1,2,3-triazole compounds could be efficiently prepared directly from the readily accessible organic azides, terminal alkynes and arylboronic acids. Advantages of the method include use of low-cost catalyst, clean oxidant, less-toxic additive, and low reaction temperature. Importantly, due to avoiding harsh strong basic reagents and high temperatures, the presented method can offer mild conditions for multi-component synthesis of 5-aryl-1,2,3-triazoles from the designed structurally complicated alkynyl or azide donors bearing natural product motifs and sensitive functional groups.
- Li, Lingjun,Li, Qianqian,Wang, Chao,Wang, Shilei,Zhu, Anlian,Zhu, Gongming
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p. 38108 - 38114
(2021/12/09)
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- A novel route to 1,4-disubstituted-1,2,3-triazoles through metal-free decarboxylative azide-alkene cycloaddition
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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.
- Rengasamy,Vijayalakshmi,Punitha,Paul Raj,Karthikeyan,Elangovan
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supporting information
(2021/10/19)
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- Discrete Benzotriazole-Copper(II) Complexes in Chelated and Non-Chelated Coordination Modes: Structural Analysis and Catalytic Application in Click and A3 Coupling Reactions
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Two copper(II) complexes with benzotriazole-based ligands having pyridyl and quinolinyl arms were synthesized in good yields and characterized fully via spectroscopic and crystallographic techniques. The crystal structures of the complexes revealed differ
- Pandey, Sharmila,Mandal, Tanmoy
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p. 1763 - 1769
(2021/05/03)
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- Multi-component reaction for the preparation of 1,5-disubstituted 1,2,3-triazoles by in-situ generation of azides and nickel-catalyzed azide-alkyne cycloaddition
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An efficient one-pot procedure combining bromide conversion into azide followed by NiAAC for the preparation of 1,5-disubstituted 1,2,3-triazoles has been developed. This procedure prevents the use of isolated azides, which are insufficiently commercially
- Camberlein, Virgyl,Kraupner, Nicolas,Bou Karroum, Nour,Lipka, Emmanuelle,Deprez-Poulain, Rebecca,Deprez, Benoit,Bosc, Damien
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supporting information
(2021/05/10)
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- Synthesis, Characterisation and Crystal structure of a New Cu(II)-carboxamide Complex and CuO nanoparticles as New Catalysts in the CuAAC reaction and Investigation of their Antibacterial activity
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The bidentate carboxamide ligand N-(thiazole-2-yl) picolinamide (LH) was synthesized in the environmentally friendly ionic liquid TBAB, and the five-coordinated CuII-complex, [Cu(L)2(H2O)].CHCl3 (1) was synthesized from LH and copper(II)acetate. Cupric oxide [CuO] nanoparticles (2) have been prepared by the thermal decomposition of (1) as a new precursor at 600 °C for 3 h under air atmosphere. (1) was characterised using FT-IR spectroscopy, elemental analyses and its solid state structure was confirmed by single crystal X-ray diffraction. (2) were identified by FT-IR spectroscopy, X-ray powder diffraction, scanning electron microscopy, energy dispersive X-ray analysis and thermo-gravimetric differential thermal analyses. The electrochemical behaviour of LH and (1) has been investigated by cyclic voltammetry: irreversible CuII/I reductions were observed. The catalytic activity of (1) and (2) were evaluated in the one-pot azide–alkyne cycloaddition click reaction in water without additional agents. LH, (1) and (2) were also screened for their in vitro antibacterial activity: they showed promising antibacterial activity comparable to that of the antibiotic penicillin.
- Kiani, Mahsa,Bagherzadeh, Mojtaba,Meghdadi, Soraia,Fadaei-Tirani, Farzaneh,Babaie, Maryam,Schenk-Jo?, Kurt
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- Synthesis, characterization and catalytic properties of a new binuclear copper(II) complex in the azide–alkyne cycloaddition
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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.
- Akbar Khandar, Ali,Amini, Mojtaba,Ellern, Arkady,Keith Woo, L.,Sheykhi, Ayda
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- Copper(I) stabilized on N,N′-methylene bis-acrylamide crosslinked polyvinylpyrrolidone: An efficient reusable catalyst for click synthesis of 1,2,3-triazoles in water
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N,N′-methylene bis-acrylamide crosslinked N-vinyl-2-pyrrolidone (NVPMBA) polymer was prepared via suspension polymerization technique and used as a polymeric support for the reduction of Cu(II) to Cu(I). It was observed that NVPMBA matrix facilitated the stabilization of Cu(I) particles. Furthermore, the copper supported polymer catalyst (CuNVPMBA) was characterized by Fourier transform infrared, X-ray diffraction, scanning electron microscopy (SEM), energy dispersive X-ray analysis, transmission electron microscope (TEM), X-ray photoelectron spectra (XPS), inductively coupled plasma optical emission spectroscopy, and derivative thermogravimetry analysis. SEM showed that both the polymer and CuNVPMBA exhibit a spherical morphology. TEM revealed that copper nanoparticles formed on the polymer surface have an average particle size of 5.14 nm. XPS analysis confirmed the presence of Cu(I) and Cu(II) in the ratio 1:2. The copper content in CuNVPMBA was found to be 1.25 wt%. CuNVPMBA was found to be very effective in promoting the click reaction between terminal alkynes and azides in aqueous media in the absence of ascorbate or external base under mild conditions to form 1,2,3-triazoles in excellent yield with a copper loading as low as 0.2 mol%. The catalyst could be reused and recycled several times without significant loss of catalytic activity.
- Mathew, Paulson,Sasidharan, Drishya,Rakesh, Nellickal Purushothaman
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- Synthesis and Characterization of Copper(I)‐Cysteine Complex Supported on Magnetic Layered Double Hydroxide as an Efficient and Recyclable Catalyst System for Click Chemistry Using Choline Azide as Reagent and Reaction Medium
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Abstract: In this study, Fe3O4@LDH@cysteine–Cu(I) nanoparticles as a novel and recyclable catalytic system was designed and successfully synthesized. These nanoparticles show high catalytic activity for preparation of the triazole fa
- Pazoki, Farzane,Salamatmanesh, Arefe,Bagheri, Sepideh,Heydari, Akbar
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p. 1186 - 1195
(2019/11/16)
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- Greener synthesis of 1,2,3-triazoles using a copper(i)-exchanged magnetically recoverable β-zeolite as catalyst
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Herein, we describe the preparation and thorough characterization of a novel magnetically recoverable copper(i)-exchanged β-zeolite and its use as an efficient catalyst for the synthesis of 1,2,3-triazoles via the one-pot three-component reaction of organic halides, terminal acetylenes, and sodium azide in water. The magnetically recoverable β-zeolite could be easily separated from the reaction mixture with the aid of a magnet and reused in several consecutive reactions. Importantly, a series of characterizations studies allowed us to disclose the mechanism for the deactivation of the catalyst, and therefore to propose a method for its reactivation.
- Andrade, Floyd C. D.,Costa, Elizama R.,De Albuquerque, Danilo Yano,Ferreira, Luanne E. M.,Lima, Carolina G. S.,Lima, Thiago M.,Paix?o, Márcio W.,Schwab, Ricardo S.,Silva, Domingos S. A.,Urquieta-González, Ernesto A.
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p. 15046 - 15053
(2020/10/02)
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- METHOD FOR PREPARING CHEMOSELECTIVE TRIAZOLE DERIVATIVES THROUGH MISCIBILITY WITH REACTION SOLVENT
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The present invention relates to a chemoselective method for preparing a triazole using a difference in miscibility with a reaction solvent. Particularly, the chemoselective method for preparing a triazole includes the steps of: carrying out a chemoselect
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Paragraph 0160-0168
(2020/11/13)
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- Visible-Light-Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron-Transfer Strategy
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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.
- Wu, Zheng-Guang,Liao, Xiang-Ji,Yuan, Li,Wang, Yi,Zheng, You-Xuan,Zuo, Jing-Lin,Pan, Yi
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p. 5694 - 5700
(2020/04/24)
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- Sequencing [3+2]-cycloaddition and multicomponent reactions: A regioselective microwave-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles using ionic liquid supported Cu(II) precatalysts in methanol
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Heterocyclic compounds with two to three nitrogen atoms play a pivotal role in the normal life cycle of a cell. Further the design and synthesis of a quality heterocyclic compound library with N-atoms as new chemical probes active, is vital in drug discov
- Saikia, Ananya Anubhav,Nishanth Rao,Das, Soumyadip,Jena, Sushovan,Rej, Sourav,Maiti, Barnali,Chanda, Kaushik
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- Dinuclear Cu(I) Halides with Terphenyl Phosphines: Synthesis, Photophysical Studies, and Catalytic Applications in CuAAC Reactions
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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
- Beltrán, álvaro,Gata, Inmaculada,Maya, Celia,Avó, Jo?o,Lima, Jo?o Carlos,Laia, César A. T.,Peloso, Riccardo,Outis, Mani,Nicasio, M. Carmen
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supporting information
p. 10894 - 10906
(2020/08/12)
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- Multicomponent click reactions catalysed by copper(I) oxide nanoparticles (Cu2ONPs) derived using Oryza sativa
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Abstract: A procedure for the expedient synthesis of well-characterized Cu(I) oxide nanoparticles (Cu2ONPs) from Cu(II) salts by employing Rice (Oryza sativa) as a cheap and ready source of reducing as well as stabilizing agent has been demonstrated. The judicious choice of rice as a catalyst has helped in the symbiotic combination of two events: viz., acidic hydrolysis of starch to form glucose and the subsequent formal reduction of Cu2+ by the in-situ generated monosaccharide reducing sugar (glucose) under the alkaline condition to produce Cu2O. Further, rice was also found to be effectively stabilizing the nanoparticles from agglomeration. Optical and microscopic techniques were suitably employed for the characterization of the nanoparticles of approximately 10 nm size. Furthermore, the specifically generated nanoparticles were found to be active catalysts in an aqueous medium for Azide-alkyne Huisgen cycloaddition (Click reaction) under base free condition via one-pot multi-component addition for the synthesis of mono-, bis- and tris-1,2,3-triazoles in good to excellent yields. Graphic abstract: Cu2ONPs synthesized using hydrolysed Rice, an active catalyst for synthesis of mono-, bis- and tris-1,4-disubstituted 1,2,3-triazoles via one pot multicomponent reactions in water.[Figure not available: see fulltext.].
- Chand, Dillip Kumar,Rai, Randhir
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- Click reactions catalyzed by Cu(I) complexes supported with dihydrobis(2-mercapto-benzimidazolyl)borate and phosphine ligands
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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(
- Khalili, Dariush,Evazi, Roya,Neshat, Abdollah,Aboonajmi, Jasem,Osanlou, Farzane
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supporting information
(2020/03/10)
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- Efficient Synthesis of 5-Trifluoromethylthio-1,2,3-Triazoles: One-Pot Multicomponent Reaction from Elemental Sulfur and TMSCF 3
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A sequential multistep reaction toward 5-trifluoromethyl thio-1,2,3-triazoles has been established, starting from alkynes, organo azides, S 8, and (trifluoromethyl)trimethylsilane (TMSCF 3). This reaction features mild conditions, easy operation, and readily available substrates.
- Li, Meng-Tian,Shen, Liang-Liang,Wu, Qin-Pei,Zhang, Lin-Lin
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supporting information
p. 304 - 310
(2019/12/30)
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- A Scalable Metal-, Azide-, and Halogen-Free Method for the Preparation of Triazoles
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A scalable metal-, azide-, and halogen-free method for the synthesis of substituted 1,2,3-triazoles has been developed. The reaction proceeds through a 3-component coupling of α-ketoacetals, tosyl hydrazide, and a primary amine. The reaction shows outstanding functional-group tolerance with respect to both the α-ketoacetal and amine coupling partners, providing access to 4-, 1,4-, 1,5-, and 1,4,5-substituted triazoles in excellent yield. This robust method results in densely functionalised 1,2,3-triazoles that remain challenging to prepare by azide–alkyne cycloaddition (AAC, CuAAC, RuAAC) methods and can be scaled in either batch or flow reactors. Methods for the chemoselective reaction of either aliphatic amines or anilines are also described, revealing some of the potential of this novel and highly versatile transformation.
- Clark, Peter R.,Hayes, Jerome F.,Tomkinson, Nicholas C. O.,Williams, Glynn D.
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supporting information
p. 6740 - 6744
(2020/03/23)
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- Copper-Catalyzed Decarboxylative Cycloaddition of Propiolic Acids, Azides, and Arylboronic Acids: Construction of Fully Substituted 1,2,3-Triazoles
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A copper-catalyzed decarboxylative cycloaddition of propiolic acids, azides, and arylboronic acids is described. The present reaction provides an efficient and convenient method for the synthesis of various fully substituted 1,2,3-Triazoles from readily available starting materials. A possible mechanism is proposed.
- Li, Ya-Min,Li, Yi,Wang, Xiang-Xiang,Xia, Wen-Jin,Xin, Yangchun,Ye, Rui-Rong,Zhou, Bin
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p. 3576 - 3586
(2020/03/23)
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- A Nanosized Propeller-like Polyoxometalate-linked Copper(I)-Resorcin[4]arene for Efficient Catalysis
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The design and assembly of polyoxometalate-resorcin[4]arene-based metal-organic molecular materials are particularly attractive for their elegant structures and potential functions. By applying a newly designed resorcin[4]arene ligand (TPC4R-II), a copper(I)-coordinated polyoxometalate-based metal-organic molecular material, namely, [CuI6(Br)3(TPC4R-II)3(PMo12O40)]·8H2O (1), was rationally assembled. Three copper(I)-coordinated resorcin[4]arenes are held together by a central [PMo12O40]3- to yield a supramolecular propeller. 1 features efficient catalytic performances for oxidation desulfurization (ODS) and azide-alkyne cycloaddition (AAC) reactions. This work affords a feasible method for the nanosized polyoxometalate-based metal-resorcin[4]arene assemblies by well combinating two types of large composites as well as low coordination metal cations.
- Guo, Ting-Ting,Ma, Jian-Fang,Xiong, Yan-Ling,Yang, Jin,Yu, Ming-Yue
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p. 15402 - 15409
(2020/11/02)
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- Electrochemical synthesis of copper(i) acetylides: Via simultaneous copper ion and catalytic base electrogeneration for use in click chemistry
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We report an efficient and sustainable electrochemical synthesis of copper(i) acetylides using simultaneous copper oxidation and Hofmann elimination of quaternary ammonium salts. The electrochemically-generated base was also regenerated electrochemically,
- Seavill, Peter W.,Holt, Katherine B.,Wilden, Jonathan D.
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p. 29300 - 29304
(2019/09/30)
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- Green synthesis of 1,2,3-triazoles via Cu2O NPs on hydrogen trititanate nanotubes promoted 1,3-dipolar cycloadditions
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Cu2O nanoparticles supported on hydrogen trititanate nanotubes (Cu2O/HTNT) catalysts have been efficiently catalyzed the multicomponent synthesis of 1,2,3-triazoles in water at room temperature from different azide precursors, for example organic halides, sulfonates and anilines. The catalysts were synthesized by hydrothermal & wet-impregnation methods and was characterized by HR-TEM, EDS, XRD, XPS, N2-adsorption desorption and ICP-MS analysis. The catalyst could be recycled by centrifugation and reused up to seven cycles. The 1-benzyl-4-(4-chlorophenyl)-1H-1,2,3-triazole (25) structure was proven by single crystal X-ray diffraction studies.
- Bhoomireddy, Rajendra Prasad Reddy,Narla, L.G. Bhavani,Peddiahgari, Vasu Govardhana Reddy
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- Iodine-mediated C-N and N-N bond formation: A facile one-pot synthetic approach to 1,2,3-triazoles under metal-free and azide-free conditions
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A novel strategy towards the synthesis of 1,4-disubstituted 1,2,3-triazoles via C-N and N-N bond formation has been demonstrated under transition metal-free and azide-free conditions. These 1,2,3-triazoles were obtained in a regioselective manner from commercially available anilines, aryl alkenes/aryl alkynes and N-tosylhydrazines using I2 under O2 atmosphere. Broad substrate scope, milder reaction conditions, good to moderate yields and clean protocol are the notable features of the method. Moreover, this protocol is amenable for the generation of a library of medicinally important key building blocks.
- Mani, Geeta Sai,Donthiboina, Kavitha,Shaik, Siddiq Pasha,Shankaraiah, Nagula,Kamal, Ahmed
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p. 27021 - 27031
(2019/09/13)
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- Preparation and investigation of copper–manganese mixed oxides as a high-efficiency catalyst for the azide-alkyne 1,3-dipolar cycloaddition reaction
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The present work is developed for the catalysis of azide-alkyne 1,3-dipolar cycloaddition reaction with the aid of copper–manganese mixed oxides nanoparticles. The Cu/MnOx nanoparticles have been synthesized by a coprecipitation procedure. Characterizatio
- Amini, Mojtaba,Salmani, Somaiyeh,Gautam, Sanjeev,Chae, Keun Hwa
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- Synthesis, characterization, and comparison of two new copper(II)complexes containing Schiff-base and diazo ligands as new catalysts in CuAAC reaction
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Two copper(II)complexes were synthesized through the reaction of Cu(OAc)2·H2O with a Schiff-base ligand (1-(((3,4-dichlorophenyl)imino)methyl)naphthalen-2-ol)and a diazo ligand (1-((3,4-dichlorophenyl)diazenyl)naphthalen-2-ol)in methanol. The complexes and ligands were characterized employing elemental analysis and electronic spectra. In addition, the ligands were fully characterized by using several 1D and 2D NMR techniques. Single crystal X-ray crystallography was also used for the characterization of some of these materials. Due to finding out the effect of Schiff-base and diazo ligands nature on the catalytic activity, the complexes were catalytically compared in one-pot azide-alkyne cycloaddition reaction in water. Furthermore, computational studies were performed on ligands and complexes for further understanding of the relationship between structure, bonding, and reactivity of these new materials.
- Bagherzadeh, Mojtaba,Mahmoudi, Hamed,Ataie, Saeed,Hafezi-Kahnamouei, Mohammad,Shahrokhian, Saeed,Bellachioma, Gianfranco,Vaccaro, Luigi
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supporting information
p. 213 - 220
(2019/05/01)
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- Method used for synthesizing 1, 4-substituted 1, 2, 3-triazole from terminal alkyne multiple components
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The invention belongs to the technical field of nitrogen containing compound preparation, and discloses a method used for synthesizing 1, 4-substituted 1, 2, 3-triazole from terminal alkyne multiple components. The method comprises following steps: 1.2 eq
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Paragraph 0092; 0093
(2019/12/08)
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- 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
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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.
- Khalili, Dariush,Rezaee, Meysam
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