852657-84-2Relevant academic research and scientific papers
Determining the Origin of Rate-Independent Chemoselectivity in CuAAC Reactions: An Alkyne-Specific Shift in Rate-Determining Step
Seath, Ciaran P.,Burley, Glenn A.,Watson, Allan J. B.
, p. 3314 - 3318 (2017)
We report a kinetic and spectroscopic analysis of alkyne-dependent chemoselectivity in the copper-catalyzed azide–alkyne click (CuAAC) reaction. Studies of six alkyne subtypes reveal that the rate-determining step (RDS) of an aromatic ynamine class is shi
Synthesis of 5-organostibano-1H-1,2,3-triazoles by Cu-catalyzed azide-alkyne cycloaddition and their application in the acyl-induced deantimonation for the preparation of fully substituted 5-acyl-1,2,3-triazoles
Yamada, Mizuki,Matsumura, Mio,Murata, Yuki,Kawahata, Masatoshi,Saito, Kohki,Kakusawa, Naoki,Yamaguchi, Kentaro,Yasuike, Shuji
, p. 2614 - 2622 (2017)
The Cu-catalyzed azide-alkyne cycloaddition by the reaction of various ethynylstibanes with benzylazide in the presence of CuBr (5?mol%) under aerobic conditions led to the formation of trisubstituted 5-organostibano-1H-1,2,3-triazoles. Further, the acyl-induced deantimonation of 5-stibanotriazoles with acyl chlorides in the presence of N,N-dimethyl-4-aminopyridine and triethylamine afforded the corresponding trisubstituted 5-acyltriazoles in moderate-to-good yields.
CuO–NiO bimetallic nanoparticles supported on graphitic carbon nitride with enhanced catalytic performance for the synthesis of 1,2,3-triazoles, bis-1,2,3-triazoles, and tetrazoles in parts per million level
Gajurel, Sushmita,Dam, Binoyargha,Bhushan, Mayank,Singh, L. Robindro,Pal, Amarta Kumar
, (2021/12/09)
The unification of CuCl2·2H2O and NiCl2·6H2O with the support of graphitic carbon nitride yielded to form an efficient, synergistic, bimetallic nano-catalyst CuO–NiO@g-C3N4. FT-IR, SEM, TEM
Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air
Ji, Jian,Guan, Cong,Wei, Qinghua,Chen, Xuwen,Zhao, Yun,Liu, Shunying
supporting information, p. 132 - 136 (2022/01/04)
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%).
Copper(I)-chitin biopolymer based: An efficient and recyclable catalyst for click azide–alkyne cycloaddition reactions in water
Bahsis, Lahoucine,Ablouh, El-Houssaine,Hachim, Mouhi Eddine,Anane, Hafid,Taourirte, Moha,Julve, Miguel,Stiriba, Salah-Eddine
, (2021/04/27)
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
vvComplexation of copper ion-containing immobilized ionic liquid in designed hierarchical-functionalized layered double hydroxide nanoreactor for azide–alkyne cycloaddition reaction
Afzali, Elham,Akbarzadeh, Azim,Mirjafary, Zohreh,Saeidian, Hamid
, (2021/08/25)
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.
Homogeneous and noncovalent immobilization of NHC-Cu catalyzed azide-alkyne cycloaddition reaction
Zhang, Xiangjie,Wang, Bingyang,Lu, Yanmei,Xia, Chungu,Liu, Jianhua
, (2021/02/26)
A series of new pyrene tagged nitrogen heterocyclic carbene copper (NHC-Cu) molecular complexes were synthesized and characterized by 1H- and 13C-NMR, high resolution ESI-mass spectrometry (HR-MS). The corresponding NHC-Cu complex was immobilized onto the surface of multi-walled carbon nanotubes (MWNTs) by using π-π stacking interaction, the noncovalent immobilization catalytic material MWNTs@NHC-Cu were characterized by FT-IR, XRD, XPS, thermogravimetry (TGA) and TEM. The new NHC-Cu complexes were tested both in the homogeneous phase and once immobilized onto multi-walled carbon nanotubes support for the azide-alkyne cycloaddition reaction. Both were active in the two-component click cycloaddition reaction of terminal alkynes and organic azides and three-component cycloaddition reaction that employs various terminal alkynes, NaN3 and organic halides with the advantage of excellent yields, low catalyst dosage, short reaction time. The MWNTs@NHC-Cu catalyst could be separated from the reaction system at the end of the reaction and reused in another catalytic cycle, but with loss of product yield.
A new amido-phosphane as ligand for copper and silver complexes. Synthesis, characterization and catalytic application for azide-alkyne cycloaddition in glycerol
Guedes Da Silva, M. Fátima C.,Mahmoud, Abdallah G.,Pombeiro, Armando J. L.
, p. 6109 - 6125 (2021/05/19)
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
Copper immobilized on biomimetic assembled calcium carbonate/carboxymethylcellulose hybrid: a highly active recoverable catalyst for CuAAC reactions
Zhang, Mingjuan,Xu, Jinxi,Zhang, Tianzhu,Li, Yiqun
, p. 3883 - 3898 (2021/05/11)
A novel copper immobilized on biomimetic assembled carboxymethylcellulose/calcium carbonate hybrid (CuII@CMC/CaCO3) as an efficient heterogeneous catalyst for the synthesis of 1,2,3-triazoles has been described herein. The fabrication of CuII@CMC/CaCO3 is accomplished through a bioinspired mineralization process using sodium carboxymethylcellulose (CMC-Na) as the template and ion exchange agent, while the metathesis, nucleation, assemble, hybridization, and immobilization of Cu(II) occurred by successful treatment with CaCl2, Na2CO3, and CuSO4 in water at room temperature. The resultant CuII@CMC/CaCO3 hybrid was well characterized by various analyses such as FT-IR, XRD, SEM, EDX, EDX-mapping, TEM, and TGA techniques. In the presence of low copper loading of CuII@CMC/CaCO3 hybrid, benzylic halides, azide, and alkynes proceeded smoothly to afford 1,4-disubstituted 1,2,3-triazoles in high yields. The catalyst can be conveniently recovered from the reaction mixture by filter and reused for at least 5 consecutive runs with a slight drop in its catalytic activity. The remarkable activity and stability of the catalyst may be attributed to the coordination of both carboxyl and hydroxyl groups of the hybrid of CMC/CaCO3.
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
Xu, Zhian,Xu, Jinxi,Li, Yiqun
, (2021/07/06)
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
