- Efficient copper-catalyzed tandem oxidative iodination and alkyne-azide cycloaddition in the presence of glycine-type ligands
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Tandem oxidative iodination and alkyne-azide cycloaddition reaction has provided one of the most widely used methods for preparation of 5-iodo-1,2,3-triazoles. However, stoichiometric copper salts are involved in this type of reaction in order to enhance
- Yuan, Donghe,Wang, Shilei,Zhu, Gongming,Zhu, Anlian,Li, Lingjun
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Read Online
- Recyclable Cu(i)/melanin dots for cycloaddition, bioconjugation and cell labelling
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Development of biocompatible and high-performance heterogeneous catalysts for bioconjugation and cell labeling is highly challenging. Melanin has previously been used as a target for melanoma imaging and therapy. Herein, this important biomarker was trans
- Sun, Yao,Hong, Suhyun,Ma, Xiaowei,Cheng, Kai,Wang, Jing,Zhang, Zhe,Yang, Meng,Jiang, Yuxin,Hong, Xuechuan,Cheng, Zhen
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Read Online
- 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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- Highly Efficient and Stable Atomically Dispersed Cu Catalyst for Azide-Alkyne Cycloaddition Reaction
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In this study, we report a highly stable and efficient single-atom Cu dispersed on N-doped porous carbon as a superior catalyst for azide-alkyne cycloaddition reaction. A broad set of 1,4-disubstituted 1,2,3-triazoles was synthesized in high to excellent
- Ren, Peng,Li, Qinglin,Song, Tao,Wang, Zhaozhan,Motokura, Ken,Yang, Yong
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p. 3960 - 3966
(2021/07/21)
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- Copper-polymer nanocomposite: An efficient catalyst for green Huisgen click synthesis
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A new method for Huisgen [3+2] cycloaddition synthesis of 1,4- and 1,4,5-substituted-1H-1,2,3-triazoles was reported. The reaction was catalyzed by the product of thermolysis of copper (II) poly-5-vinyltetrazolate. Heterogeneous catalyst includes copper nanoparticles which supported on polymeric matrix. It presents recovered and recycled catalyst and the catalyzed reaction proceeds in aerobic conditions at room temperature in aqueous media.
- Zuraev, Alexander V.,Grigoriev, Yuri V.,Budevich, Vladislav A.,Ivashkevich, Oleg A.
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supporting information
p. 1583 - 1586
(2018/03/23)
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- A Small Library of 1,2,3-Triazole Analogs of CAP-55: Synthesis and Binding Affinity at Nicotinic Acetylcholine Receptors
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Alpha7 nicotinic acetylcholine receptor is emerging as a central regulator in inflammatory processes, as documented by increasing studies reported in the literature. For instance, the activation of this nicotinic receptor subtype in resident macrophages inhibits the production of pro-inflammatory cytokines, thereby attenuating local inflammatory responses, and may open a new window in the treatment of chronic inflammatory disease, such as Crohn's disease, rheumatoid arthritis, psoriasis, and asthma. In continuation of our ongoing research for the development of new cholinergic drug candidates, we selected the nicotine derivative CAP55, which was previously shown to exert anti-inflammatory effects via nicotinic stimulation, as a suitable compound for lead optimization. Through the isosteric replacement of its 3,5-disubstituted 4,5-dihydroisoxazole core with a 1,4-disubstituted 1,2,3-triazole ring, we could rapidly generate a small library of CAP55-related analogs via a one-pot copper(I)-catalyzed azide-alkyne cycloaddition. Receptor binding assays at nAChRs led to the identification of two promising derivatives, compounds 4 and 10, worthy of further pharmacological studies.
- Rizzi, Luca,Gotti, Cecilia,De Amici, Marco,Dallanoce, Clelia,Matera, Carlo
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- CuI/Et 2 NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol
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A concise one-pot three-component reaction of organic halides, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solven
- Guo, Shengqiang,Zhou, Yang,Dai, Bencai,Huo, Cuimeng,Liu, Changchun,Zhao, Yongde
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supporting information
p. 2191 - 2199
(2018/04/05)
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- Synthesis of a heterogeneous Cu(OAc)2-anchored SBA-15 catalyst and its application in the CuAAC reaction
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A novel dinuclear Cu(OAc)2-anchored SBA-15 catalyst was synthesized by simple proton exchange of a carboxyl functionalized mesoporous SBA-15 silica with Cu(OAc)2 in water. XAFS and EPR spectra were utilized to probe its structure. Su
- Sun, Nan,Yu, Zhongqi,Yi, Hong,Zhu, Xiayue,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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supporting information
p. 1612 - 1616
(2018/02/09)
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- Cobaltocene Reduction of Cu and Ag Salts and Catalytic Behavior of the Nanoparticles Formed
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The modes of generation of nanoparticles (NPs) are of great interest for multiple applications in catalysis, optics, sensing, and nanomedicine. Here, fast reduction of CuSO4·5H2O and Ag salts by commercial cobaltocene yields small, stable, water-soluble Cu and Ag NPs with a narrow size distribution without any other ligand or support. The variation of the Ag salt counteranion (NO3-, F-, BF4-) strongly influences both the plasmonic absorption of the AgNPs synthesized in this way and the high apparent rate constant of the AgNP-catalyzed reduction of 4-nitrophenol by NaBH4, showing that the precursor counteranion binds to the AgNP surface. The CuNPs synthesized from CuSO4 and cobaltocene are a recyclable catalyst for the Cu-catalyzed alkyne-azide cycloaddition reaction in water extended to various azides and alkynes, including functionalization of compounds of biomedical interest. Both CuNP and AgNP catalytic activities are also very promising signs for further extension to a variety of other truly efficient metal-NP-catalyzed reactions.
- Fu, Fangyu,Ciganda, Roberto,Wang, Qi,Tabey, Alexis,Wang, Changlong,Escobar, Ane,Martinez-Villacorta, Angel M.,Hernández, Ricardo,Moya, Sergio,Fouquet, Eric,Ruiz, Jaime,Astruc, Didier
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p. 8100 - 8106
(2018/08/03)
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- Design and Applications of an Efficient Amphiphilic "click" CuI Catalyst in Water
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The copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) using the conventional Sharpless-Fokin catalyst that consists of CuSO4 + Na ascorbate, the most well-known and used "click" reaction, is considerably accelerated by the addition of a tr
- Wang, Changlong,Wang, Dong,Yu, Shilin,Cornilleau, Thomas,Ruiz, Jaime,Salmon, Lionel,Astruc, Didier
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p. 5424 - 5431
(2016/08/18)
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- Cu(II)-Catalyzed Oxidative Formation of 5,5′-Bistriazoles
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Copper(II) acetate under aerobic conditions catalyzes the formation of 5,5′-bis(1,2,3-triazole)s (5,5′-bistriazoles) from organic azides and terminal alkynes. This reaction is an oxidative extension of the widely used copper-catalyzed azide-alkyne “click”
- Brassard, Christopher J.,Zhang, Xiaoguang,Brewer, Christopher R.,Liu, Peiye,Clark, Ronald J.,Zhu, Lei
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p. 12091 - 12105
(2016/12/23)
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- Highly efficient click reaction on water catalyzed by a ruthenium complex
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The highly efficient click reaction between terminal alkynes and azides has been achieved on water using ruthenium complex RuH2(CO)(PPh3)3 as the catalyst, and the catalyst loading was decreased to 0.2 mol% on water from 5
- Siyang, Hai Xiao,Liu, Hui Ling,Wu, Xin Yan,Liu, Pei Nian
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p. 4693 - 4697
(2015/02/19)
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- Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira-Click and Click-Heck reactions
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This paper describes the development of one-pot sequential Sonogashira-Click and Click-Heck reactions by using Pd-Cu/C as a heterogeneous multi-task catalyst for the synthesis of heterocyclic structures. Details of the optimization studies and the substrate scope are discussed. These methodologies allow the preparation of functionalized triazoles in simple experimental conditions with inexpensive reagents.
- Rossy, Cybille,Majimel, Jér?me,Delapierre, Mona Tréguer,Fouquet, Eric,Felpin, Fran?ois-Xavier
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- Recyclable catalytic dendrimer nanoreactor for part-per-million Cu I catalysis of "click" chemistry in water
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Upon catalyst and substrate encapsulation, an amphiphilic dendrimer containing 27 triethylene glycol termini and 9 intradendritic triazole rings serves as a catalytic nanoreactor by considerably accelerating the Cu I-catalyzed alkyne-azide cycl
- Deraedt, Christophe,Pinaud, No?l,Astruc, Didier
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supporting information
p. 12092 - 12098
(2014/10/16)
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- A highly active and magnetically recoverable tris(triazolyl)-CuI catalyst for alkyne-azide cycloaddition reactions
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Nanoparticle-supported tris(triazolyl)-CuBr, with a diameter of approximately 25 nm measured by TEM spectroscopy, has been easily prepared, and its catalytic activity was evaluated in the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. In in
- Wang, Dong,Etienne, Laetitia,Echeverria, Maria,Moya, Sergio,Astruc, Didier
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p. 4047 - 4054
(2014/04/17)
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- Selective formation of 1,4-disubstituted triazoles from ruthenium-catalyzed cycloaddition of terminal alkynes and organic azides: Scope and reaction mechanism
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The catalytic activity of a series of ruthenium complexes lacking cyclopentadienyl ligands has been evaluated for the cycloaddition of terminal alkynes and azides to give selectively 1,4-disubstituted 1,2,3-triazoles. The complex RuH(η2-BH
- Liu, Pei Nian,Li, Juan,Su, Fu Hai,Ju, Kun Dong,Zhang, Li,Shi, Chuan,Sung, Herman H. Y.,Williams, Ian D.,Fokin, Valery V.,Lin, Zhenyang,Jia, Guochen
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experimental part
p. 4904 - 4915
(2012/09/22)
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- Ligand-assisted, copper(II) acetate-accelerated azide-alkyne cycloaddition
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Polytriazole ligands such as the widely used tris[(1-benzyl-1H-1,2,3- triazol-4-yl)methyl]amine (TBTA), are shown to assist copper(II) acetate-mediated azide-alkyne cycloaddition (AAC) reactions that involve nonchelating azides. Tris(2-{4-[(dimethylamino)
- Michaels, Heather A.,Zhu, Lei
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supporting information; experimental part
p. 2825 - 2834
(2012/06/05)
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- Non-magnetic and magnetic supported copper(I) chelating adsorbents as efficient heterogeneous catalysts and copper scavengers for click chemistry
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Novel supported chelating adsorbents bearing diverse multidentate nitrogenated ligands with strong copper(I) affinities are easily prepared in non-magnetic and magnetic variants using silica and silica-coated magnetite nanoparticles as suitable supports a
- Megia-Fernandez, Alicia,Ortega-Munoz, Mariano,Lopez-Jaramillo, Javier,Hernandez-Mateo, Fernando,Santoyo-Gonzalez, Francisco
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supporting information; experimental part
p. 3306 - 3320
(2011/02/23)
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- The sequential Sonogashira-click reaction: A versatile route to 4-aryl-1,2,3-triazoles
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Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.
- Loerincz, Krisztian,Kele, Peter,Novak, Zoltan
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experimental part
p. 3527 - 3532
(2010/02/28)
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- CYCLOADDITION OF AZIDES AND ALKYNES
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This invention provides a process which comprises contacting, in a reaction zone, at least one organic azide, at least one alkyne, and at least one N-heterocyclic carbene copper compound in which the ligands are either (i) a halide and an N-heterocyclic c
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Page/Page column 8
(2009/04/24)
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- [(NHC)2Cu]X complexes as efficient catalysts for azide-alkyne click chemistry at low catalyst loadings
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(Chemical Equation Presented) La click, c'est chic! A catalytic system based on an [(NHC)2Cu]X complex (NHC=N-heterocyclic carbene) was developed for the [3+2] cycloaddition of azides with alkynes under click conditions (see scheme). This syste
- Diez-Gonzlez, Silvia,Nolan, Steven P.
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supporting information; experimental part
p. 8881 - 8884
(2009/05/26)
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