- Preparation of ruthenium azido complex containing a Tp ligand and ruthenium-catalyzed cycloaddition of organic azides with alkynes in organic and aqueous media: Experimental and computational studies
-
The catalytic activity of a series of ruthenium azido complexes containing Tp ligands has been evaluated for the cycloaddition of terminal alkynes and azides to give selectively 1,5-disubstituted 1,2,3-triazoles. The complex Tp(PPh3)(EtNH2)RuN3 (2, Tp = HB(pz)3, pz = pyrazolyl) was found to be an effective catalyst for the cycloaddition reactions. In the presence of complex 2, azides reacted with a range of terminal alkynes containing various functionalities to selectively produce 1,5-disubstituted 1,2,3-triazoles. Theoretical calculations support the proposed mechanism.
- Wang, Tsang-Hsiu,Wu, Feng-Ling,Chiang, Guan-Ru,He, Sheng-Ting,Lo, Yih-Hsing
-
-
Read Online
- Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air
-
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
-
supporting information
p. 132 - 136
(2022/01/04)
-
- 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
-
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
-
supporting information
(2021/05/10)
-
- Copper-Catalyzed Decarboxylative Cycloaddition of Propiolic Acids, Azides, and Arylboronic Acids: Construction of Fully Substituted 1,2,3-Triazoles
-
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
-
p. 3576 - 3586
(2020/03/23)
-
- Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles by 1,3-dipolar cycloaddition: Role of Er(OTf)3, ionic liquid and water
-
A simple procedure to obtain 1,5-disubstituted 1,2,3-triazoles, using the Er(OTf)3/[mpy]OTf/H2O catalytic system is described. The reaction proceeds through an eliminative azide–olefin cycloaddition (EAOC) offering a highly regiosele
- Maiuolo, Loredana,Russo, Beatrice,Algieri, Vincenzo,Nardi, Monica,Di Gioia, Maria Luisa,Tallarida, Matteo Antonio,De Nino, Antonio
-
supporting information
p. 672 - 674
(2019/02/03)
-
- Novel synthesis of 1,5-disubstituted-1,2,3-triazolines catalysed by Zepto magnetic microspheres under the influence of a rotating magnetic field
-
The novel reactor has been designed to perform chemical reactions under the influence of a magnetic field generated by alternating magnetic poles as a function of time. The system was successfully employed to synthesize a series of 1,5-disubstituted-1,2,3-triazolines via the regioselective [3 + 2] cycloaddition reactions between alkyl/aryl azides and nitroolefins catalysed by Zepto (para magnetic ultra-blue carboxy functionalized) microspheres (bead diameter 2.5 μm). All of the reactions went smoothly without any adverse effect on nitro, cyano, thienyl, hydroxy, halogens, and ether functions at 25 ± 2 °C and afforded 82%-99% pure products at a magnetic field of 18.99 mT and an exposure time of 180-240 min. The influence of the magnetic force exerted on the magnetic materials was found to enhance the catalytic activity of microspheres. The catalyst could easily be separated by simple centrifugation, which could be reused for at least 15 runs with no loss in activity.
- Sharma, Priyanka,Vallabhapurapu, Srinivasu V.,Ho, Wei H.,Hemmaragala, Nanjundaswamy M.
-
p. 163 - 168
(2019/03/05)
-
- Multi-component reaction-functionalized chitosan complexed with copper nanoparticles: An efficient catalyst toward A3 coupling and click reactions in water
-
A novel bio-nanocomposite nanocatalyst with highly dispersed particles is synthesized through covalent functionalization of chitosan biopolymer by the multicomponent reaction (MCR) strategy. Surface functionalization of chitosan through MCR is led to the
- Shaabani, Ahmad,Shadi, Mehrdad,Mohammadian, Reza,Javanbakht, Siamak,Nazeri, Mohammad Taghi,Bahri, Fereshteh
-
-
- Ag-NHC anchored on silica: An efficient ultra-low loading catalyst for regioselective 1,2,3-triazole synthesis
-
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
-
supporting information
p. 19331 - 19337
(2019/12/24)
-
- Double-functional group 4 - TMS - 5 - I - 1, 2, 3 - triazole class compound and its preparation method and application
-
The invention discloses a bifunctional 4-TMS-5-I-1,2,3-triazole compound as well as a preparation method and application thereof. According to the technical scheme, the bifunctional 4-TMS-5-I-1,2,3-triazole compound is characterized by being prepared at normal temperature, wherein trimethyl silyl acetylene and nitrine serve as raw materials, acetonitrile serves as a solvent, cuprous iodide serves as a catalyst, N-chlorosuccinimide serve as an oxidant, and N-di(isopropyl)ethylamine serves as an alkali. The bifunctional 4-TMS-5-I-1,2,3-triazole compound has a structural formula as shown in the specification, wherein R is as shown in the specification. The invention further discloses a preparation method of the bifunctional 4-TMS-5-I-1,2,3-triazole compound and a method of further synthesizing a 1,5-di-substituted-1,2,3-triazole compound from the bifunctional 4-TMS-5-I-1,2,3-triazole compound which serves as an intermediate. The raw materials are wide in source, are easy to prepare and are low in cost, and the cuprous iodide adopted by reaction serves as the catalyst and the reactant, is very low in cost, is simple and is easy to obtain.
- -
-
Paragraph 0043-0044
(2018/05/16)
-
- CuO-Nanoparticles Catalyzed Synthesis of 1,4-Disubstituted-1,2,3-Triazoles from Bromoalkenes
-
Abstract: A novel and efficient protocol involving commercially available CuO nanoparticles (CNP) as catalyst has been developed for the synthesis of 1,2,3-triazoles. A library of 1,4-disubstituted 1,2,3-triazoles has been constructed with good to excellent yields. Graphical Abstract: SynopsisA novel and efficient protocol involving commercially available CuO nanoparticles (CNP) as catalyst has been developed for the synthesis of 1,2,3-triazoles. A library of 1,4-disubstituted 1,2,3-triazoles has been constructed with good to excellent yields.[Figure not available: see fulltext.].
- Raj, John Paul,Gangaprasad, Dasari,Vajjiravel, Murugesan,Karthikeyan, Kesavan,Elangovan, Jebamalai
-
-
- Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents
-
A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.
- Cui, Fei-Hu,Chen, Jing,Mo, Zu-Yu,Su, Shi-Xia,Chen, Yan-Yan,Ma, Xian-Li,Tang, Hai-Tao,Wang, Heng-Shan,Pan, Ying-Ming,Xu, Yan-Li
-
supporting information
p. 925 - 929
(2018/02/22)
-
- Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study
-
This diagnostic study aims to shed light on the catalytic activity of a library of Cu(ii) based coordination compounds with benzotriazole-based ligands. We report herein the synthesis and characterization of five new coordination compounds formulated as [CuII(L4)(MeCN)2(CF3SO3)2] (1), [CuII(L5)2(CF3SO3)2] (2), [CuII(L6)2(MeCN)(CF3SO3)]·(CF3SO3) (3), [CuII(L6)2(H2O)(CF3SO3)]·(CF3SO3)·2(Me2CO) (4), and [CuI4(L1)2(L1′)2(CF3SO3)2]2·4(CF3SO3)·8(Me2CO) (5), derived from similar nitrogen-based ligands. The homogeneous catalytic activity of these compounds along with our previously reported coordination compounds (6-13), derived from similar ligands, is tested against the well-known Cu(i)-catalysed azide-alkyne cycloaddition reaction. The optimal catalyst [CuII(L1)2(CF3SO3)2] (10) activates the reaction to afford 1,4-disubstituted 1,2,3-triazoles with yields up to 98% and without requiring a reducing agent. Various control experiments are performed to optimize the method and examine parameters such as ligand variation, metal coordination geometry and environment, in order to elucidate the behaviour of the catalytic system.
- Loukopoulos, Edward,Abdul-Sada, Alaa,Csire, Gizella,Kállay, Csilla,Brookfield, Adam,Tizzard, Graham J.,Coles, Simon J.,Lykakis, Ioannis N.,Kostakis, George E.
-
p. 10491 - 10508
(2018/08/17)
-
- Investigation of copper-free alkyne/azide 1,3-dipolar cycloadditions using microwave irradiation
-
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.
-
supporting information
p. 81 - 84
(2017/12/28)
-
- Convergent synthesis of trifunctional molecules by three sequential azido-type-selective cycloadditions
-
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
-
supporting information
p. 3705 - 3708
(2018/04/17)
-
- CuI@UiO-67-IM: A MOF-Based Bifunctional Composite Triphase-Transfer Catalyst for Sequential One-Pot Azide-Alkyne Cycloaddition in Water
-
A CuI-loaded and n-pentadecyl-attached imidazolium salt decorated UiO-67-type metal-organic framework (CuI@UiO-67-IM, 2) based on a new premodified ligand L (n-pentadecyl-attached imidazolium (IM) decorated dicarboxylic acid) and ZrCl4 is reported. Compound 2 can be a bifunctional composite heterogeneous phase-transfer catalyst to promote the azide-alkyne cycloaddition (H2O, air, 80 °C) from corresponding halogenated compounds and sodium azide as a sequential one-pot procedure with high yields and excellent regioselectivity.
- Hu, Yu-Hong,Wang, Jian-Cheng,Yang, Song,Li, Yan-An,Dong, Yu-Bin
-
p. 8341 - 8347
(2017/07/22)
-
- Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
-
Transition-metal-catalyzed or metal-free azide-alkyne cycloadditions are methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide-alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.
- Kim, Woo Gyum,Kang, Mi Eun,Lee, Jae Bin,Jeon, Min Ho,Lee, Sungmin,Lee, Jungha,Choi, Bongseo,Cal, Pedro M. S. D.,Kang, Sebyung,Kee, Jung-Min,Bernardes, Gon?alo J. L.,Rohde, Jan-Uwe,Choe, Wonyoung,Hong, Sung You
-
p. 12121 - 12124
(2017/09/12)
-
- Regioselective synthesis of functionalized 1,2,3-triazoles via oxidative [3+2]-cycloaddition using Zn(OAc)2 - tBuOOH or ZnO nanoparticle as catalyst system in aqueous medium
-
The regioselective synthesis of functionalized pyrazole?1,2,3-triazoles is reported via oxidative [3 + 2]-cycloaddition reactions of azides with β-nitrostyrenes and chalcone derivatives using Zn(OAc)2 - tBuOOH or ZnO nanoparticles as
- Paplal, Banoth,Nagaraju, Sakkani,Sridhar, Balasubramanian,Kashinath, Dhurke
-
p. 115 - 120
(2017/06/20)
-
- C-H arylations of 1,2,3-triazoles by reusable heterogeneous palladium catalysts in biomass-derived γ-valerolactone
-
C-H arylations were accomplished with a user-friendly heterogeneous palladium catalyst in the biomass-derived γ-valerolactone (GVL) as an environmentally-benign reaction medium. The user-friendly protocol was characterized by ample substrate scope and hig
- Tian, Xu,Yang, Fanzhi,Rasina, Dace,Bauer, Michaela,Warratz, Svenja,Ferlin, Francesco,Vaccaro, Luigi,Ackermann, Lutz
-
supporting information
p. 9777 - 9780
(2016/08/04)
-
- A tunable route to oxidative and eliminative [3+2] cycloadditions of organic azides with nitroolefins: CuO nanoparticles catalyzed synthesis of 1,2,3-triazoles under solvent-free condition
-
A regioselective and tunable synthesis of 1,5-disubstituted 1,2,3-triazloles from oxidative and eliminative [3+2] cycloadditions of nitroolefins and organic azides under solvent-free condition in the presence and absence of commercially available CuO nano
- Gangaprasad,Paul Raj,Kiranmye,Sasikala,Karthikeyan,Kutti Rani,Elangovan
-
supporting information
p. 3105 - 3108
(2016/07/06)
-
- Functionalized Silver Nanoparticle Catalyzed [3+2] Cycloaddition Reaction: Greener Route to Substituted-1,2,3-triazolines
-
The [3+2] cycloaddition reaction between nitroolefins and alkyl/aryl azides was studied using functionalized silver nanoparticles (FnAgNPs) of average diameter 23 ± 1 nm as catalyst produced by the plant extract Protorhus longifolia. We found FnAgNPs to c
- Hemmaragala, Nanjundaswamy Marishetty,Abrahamse, Heidi,George, Blassan Plackal Adimuriyil,Gannimani, Ramesh,Govender, Patrick
-
p. 464 - 473
(2016/02/23)
-
- Synthesis, structure, and catalytic properties of copper, palladium and cobalt complexes containing an N,O-type bidentate thiazoline ligand
-
Synthesis of CoIII, CuII and PdII complexes containing 2-(2′-hydroxyphenyl)-2-thiazoline as a bidentate O,N-donor thiazoline ligand (tzol), [Co(tzol)3] (1), [Cu(tzol)2] (2), [Pd(tzol)2] (3) and characterization by various techniques such as IR, mass spectrometry, and elemental analysis are reported. The novel complex 1 was also characterized by X-ray crystallography. The structures of complexes 2 and 3 were analyzed by density functional theory. The representative synthetic procedure involves the reaction of a metal acetate with the thiazoline ligand in methanol. The catalytic activity of complexes 1-3 for azide-alkyne cycloaddition was tested. The reaction conditions for the azide-alkyne cycloaddition were optimized by varying the catalyst loading, temperature, and time of reaction.
- Amini, Mojtaba,Bayrami, Arshad,Marashi, Mohammad Nazari,Arab, Ali,Ellern, Arkady,Woo, L. Keith
-
-
- Copper nanoparticle decorated three dimensional graphene with high catalytic activity for Huisgen 1,3-dipolar cycloaddition
-
A copper nanoparticle decorated three-dimensional graphene nanocomposite was prepared at room temperature by reduction of copper sulfate using l-ascorbic acid as the reducing agent. The synthesized Cu NPs-3D G nanocatalyst exhibited excellent catalytic ac
- Dabiri, Minoo,Kasmaei, Melika,Salari, Parinaz,Movahed, Siyavash Kazemi
-
p. 57019 - 57023
(2016/07/07)
-
- Regioselective copper-diamine-catalyzed C-H arylation of 1,2,4-triazole ring with aryl bromides
-
A convenient methodology for the regioselective C-H arylation of 1,2,4-triazole ring was developed. Using a benchtop stable Cu-diamine catalyst system, C-H functionalization of a simple 1,2,4-triazole substrate with various aryl bromides was regioselectively accomplished at the C5 position of the triazole ring.
- Jamal, Zaini,Teo, Yong-Chua
-
p. 75449 - 75452
(2016/08/24)
-
- A New Simplified Protocol for Copper(I) Alkyne-Azide Cycloaddition Reactions Using Low Substoichiometric Amounts of Copper(II) Precatalysts in Methanol
-
Copper(II) carboxylates are reduced efficiently by methanol in the presence of alkynes and form yellow alkynylcopper(I) polymeric precatalysts that are involved with azides, in the absence of added ligands, in the catalytic cycles that result in the forma
- Buckley, Benjamin R.,Figueres, Maria M. P.,Khan, Amna N.,Heaney, Harry
-
supporting information
p. 51 - 56
(2015/12/26)
-
- Metal-Organic Framework Capillary Microreactor for Application in Click Chemistry
-
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.
-
p. 1692 - 1698
(2016/05/19)
-
- Synthesis of Polysubstituted Imidazoles and Pyridines via Samarium(III) Triflate-Catalyzed [2+2+1] and [4+2] Annulations of Unactivated Aromatic Alkenes with Azides
-
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
-
p. 3229 - 3241
(2015/11/03)
-
- Synthesis of functionalized 1,2,3-triazoles using Bi2WO6 nanoparticles as efficient and reusable heterogeneous catalyst in aqueous medium
-
Synthesis of functionalized triazoles is reported via Bi2WO6 nanoparticle (10 mol%) mediated 1,3-dipolar cycloaddition reactions of β-nitrostyrenes, phenylacetylene and chalcones with azides (80 °C, 2-6 h) in water. The regioselectiv
- Paplal, Banoth,Nagaraju, Sakkani,Palakollu, Veerabhadraiah,Kanvah, Sriram,Kumar, B. Vijaya,Kashinath, Dhurke
-
p. 57842 - 57846
(2015/07/20)
-
- Copper-catalyzed [3 + 2] cycloaddition/oxidation reactions between nitro-olefins and organic azides: Highly regioselective synthesis of NO2-substituted 1,2,3-triazoles
-
A new copper-catalyzed [3 + 2] cycloaddition/oxidation reaction of nitro-olefins with organic azides has been developed to afford 1,4(-NO2),5-trisubstituted 1,2,3-triazoles. This reaction sequence has a broad substrate scope and affords NO2-substituted 1,2,3-triazoles with high regioselectivities and in good to excellent yields. The involved oxidative process overcomes the elimination of HNO2 for general cycloaddition of nitro-olefins with organic azides, which shows a high atom economy and potential applications.
- Chen, Yunfeng,Nie, Gang,Zhang, Qi,Ma, Shan,Li, Huan,Hu, Qinquan
-
supporting information
p. 1118 - 1121
(2015/03/14)
-
- 4-Trimethylsilyl-5-iodo-1,2,3-triazole: A key precursor for the divergent syntheses of 1,5-disubstituted 1,2,3-triazoles
-
Bifunctional 4-trimethylsilyl-5-iodo-1,2,3-triazoles (TMSIT) were reported in this paper, which could be efficiently synthesized directly from readily accessible TMS-alkyne, azide, and copper(I) iodide at room temperature. Using TMSIT as key precursors, a divergent protocol for the preparation of 1,5-disubstituted 1,2,3-triazoles was developed via sequential copper/palladium-catalyzed coupling reactions and desilylation in one pot.
- Li, Lingjun,Shang, Tongpeng,Ma, Xiaonan,Guo, Haiyun,Zhu, Anlian,Zhang, Guisheng
-
p. 695 - 699
(2015/03/14)
-
- Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by Reusable AlCl3 Immobilized on γ-Al2O3
-
(Chemical Equation Presented) There is rapidly growing interest in the synthesis and use of substituted 1,2,3-triazoles. We report an easy and interesting procedure that demonstrates the effectiveness of surface-modified γ-Al2O3, which is reusable, efficient, catalytic, safe, and environmentally acceptable for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via [3 + 2] cycloaddition of phenyl and benzyl azides with a series of aryl nitroolefins in good yields. No adverse effect on substituents such as nitro, cyano, hydroxy, ether linkage, and halogens was observed. The catalyst could easily be recycled and was reused for nine runs without losing its activity.
- Nanjundaswamy, Hemmaragala M.,Abrahamse, Heidi
-
p. 967 - 974
(2015/03/30)
-
- AgN(CN)2/DIPEA/H2O-EG: a highly efficient catalytic system for synthesis of 1,4-disubstituted-1,2,3 triazoles at room temperature
-
A novel, efficient and robust method for silver-catalyzed azide-alkyne cycloaddition (AgAAC) reactions in H2O/Ethylene glycol (EG) at room temperature has been developed. The protocol addresses silver dicyanamide/DIPEA as a highly effective cat
- Ali, Abdul Aziz,Chetia, Mitali,Saikia, Bishwajit,Saikia, Prakash J.,Sarma, Diganta
-
supporting information
p. 5892 - 5895
(2015/11/02)
-
- Cu2+-doped zeolitic imidazolate frameworks (ZIF-8): Efficient and stable catalysts for cycloadditions and condensation reactions
-
Cu2+-doped zeolitic imidazolate framework (ZIF) crystals were efficiently prepared by reaction of Cu(NO3)2, Zn(NO3)2, and 2-methylimidazole in methanol at room temperature. Scanning electron microscopy, transmission electron microscopy and X-ray diffraction showed that the Cu/ZIF-8 particles were nanosized (between ca. 120 and 170 nm) and that the body-centered cubic crystal lattice of the parent ZIF-8 framework is continuously maintained, regardless of the doping percentage. Moreover, thermogravimetric analyses and specific BET surface area measurements demonstrated that the doping does not alter the high stability of ZIF-8 crystals and that the porosity only decreases at a high doping percentage (25% in Cu2+). The Cu/ZIF-8 material showed excellent catalytic activity in the [3 + 2] cycloaddition of organic azides with alkynes and in Friedl?nder and Combes condensations due to the high catalyst surface area and the high dispersion of Cu/ZIF-8 particles. Notably, the Cu/ZIF-8 particles not only exhibit excellent performance but also show great stability in the reaction, allowing their reuse up to ten times in condensation reactions. Our findings explored a simple and powerful way to incorporate metal ions into the backbones of open framework materials without losing their properties.
- Schejn, Aleksandra,Aboulaich, Abdelhay,Balan, Lavinia,Falk, Véronique,Lalevée, Jacques,Medjahdi, Ghouti,Aranda, Lionel,Mozet, Kevin,Schneider, Rapha?l
-
p. 1829 - 1839
(2015/04/27)
-
- Pressure-accelerated azide-alkyne cycloaddition: Micro capillary versus autoclave reactor performance
-
Pressure effects on regioselectivity and yield of cycloaddition reactions have been shown to exist. Nevertheless, high pressure synthetic applications with subsequent benefits in the production of natural products are limited by the general availability o
- Borukhova, Svetlana,Seeger, Andreas D.,Nol, Timothy,Wang, Qi,Busch, Markus,Hessel, Volker
-
p. 504 - 512
(2015/03/04)
-
- Fe3O4@ZIF-8: Magnetically recoverable catalysts by loading Fe3O4 nanoparticles inside a zinc imidazolate framework
-
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
-
supporting information
p. 10136 - 10140
(2015/06/08)
-
- Copper-catalyzed carbon-carbon bond cleavage of primary propargyl alcohols: β-carbon elimination of hemiaminal intermediates
-
The copper-catalyzed cleavage of carbon-carbon bonds in primary propargyl alcohols under oxygen was investigated. This process involves the formation and fragmentation of hemiaminals from aldehydes (oxidized alcohols) and amines. This reaction mechanism was supported by the formation of N-formyl amines and GC experimental results.
- Kang, Ye-Won,Cho, Yu Jin,Ko, Kwang-Youn,Jang, Hye-Young
-
p. 3931 - 3934
(2015/08/03)
-
- CATALYTIC REACTION
-
A catalytic reaction comprises several steps: providing a catalyst, wherein the catalyst is metal or metal oxide particles and at least have {110} crystal plane; using the catalyst when performing a cycloaddition reaction. By using the catalyst with high
- -
-
Paragraph 0039
(2015/10/05)
-
- A metal-free three-component reaction for the regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles
-
A metal-free three-component reaction to synthesize 1,4,5-trisubstituted 1,2,3-triazoles from readily available building blocks,such as aldehydes,nitroalkanes,and organic azides,is described. The process is enabled by an organocatalyzed Knoevenagel condensation of the formyl group with the nitro compound,which is followed by the 1,3-dipolar cycloaddition of the azide to the activated alkene. The reaction features an excellent substrate scope,and the products are obtained with high yield and regioselectivity. This method can be utilized for the synthesis of fused triazole heterocycles and materials with several triazole moieties.
- Thomas, Joice,John, Jubi,Parekh, Nikita,Dehaen, Wim
-
supporting information
p. 10155 - 10159
(2015/03/31)
-
- Multicomponent azide-alkyne cycloaddition catalyzed by impregnated bimetallic nickel and copper on magnetite
-
A new bimetallic catalyst derived from nickel and copper has been used successfully for the first time in the multicomponent reaction of terminal alkynes, sodium azide, and benzyl bromide derivatives. The presence of both metallic species on the surface of magnetite seems to have a positive and synergetic effect. The catalyst loading is the lowest ever published for a catalyst of copper anchored on any type of iron support. The catalyst could be easily removed from the reaction media just by magnetic decantation and it could be reused up to ten times without any negative effect on the initial results. The Royal Society of Chemistry 2014.
- Perez, Juana M.,Cano, Rafael,Ramon, Diego J.
-
p. 23943 - 23951
(2014/06/24)
-
- Ce(OTf)3-catalyzed [3 + 2] cycloaddition of azides with nitroolefins: Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles
-
The first example of rare earth metal-catalyzed [3 + 2] cycloaddition of organic azides with nitroolefins and subsequent elimination reaction is described. In the presence of a catalytic amount of Ce(OTf)3, both benzyl and phenyl azides react with a broad range of aryl nitroolefins containing a range of functionalities selectively producing 1,5-disubstituted 1,2,3-triazoles in good to excellent yields.
- Wang, Ying-Chun,Xie, Yu-Yang,Qu, Hong-En,Wang, Heng-Shan,Pan, Ying-Ming,Huang, Fu-Ping
-
p. 4463 - 4469
(2014/06/09)
-
- A general route to 1,5-disubstituted 1,2,3-triazoles with alkyl/alkyl, alkyl/aryl, aryl/aryl combinations: A metal-free, regioselective, one-pot three component approach
-
An experimentally simple one-pot reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields by combining vinyl sulfones, sodium azide and alkyl bromides, -tosylates, -mesylates or aryl amines, -iodides is reported. The organic az
- Dey, Santu,Pathak, Tanmaya
-
p. 9275 - 9278
(2014/03/21)
-
- A metal-free multicomponent cascade reaction for the regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles
-
About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α-amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see scheme, Ts=4-toluenesulfonyl).
- Cheng, Guolin,Zeng, Xiaobao,Shen, Jinhai,Wang, Xuesong,Cui, Xiuling
-
p. 13265 - 13268
(2014/01/06)
-
- Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: New mechanistic features
-
The first example of rare earth metal-catalyzed cycloaddition of terminal alkynes to azides resulting in the formation of 1,5-disubstituted 1,2,3-triazoles is described. Preliminary studies revealed that the present cycloaddition shows unprecedented mecha
- Hong, Longcheng,Lin, Weijia,Zhang, Fangjun,Liu, Ruiting,Zhou, Xigeng
-
p. 5589 - 5591
(2013/07/25)
-
- Organic synthesis via magnetic attraction: Benign and sustainable protocols using magnetic nanoferrites
-
Magnetic nano-catalysts have been prepared using simple modification of iron ferrites. The nm size range of these particles facilitates the catalysis process, as an increased surface area is available for the reaction; the easy separation of the catalysts by an external magnet and their recovery and reuse are additional beneficial attributes. Glutathione bearing nano-ferrites have been used as organocatalysts for the Paal-Knorr reaction and homocoupling of boronic acids. Nanoferrites, post-synthetically modified by ligands, were used to immobilize nanometals (Cu, Pd, Ru, etc.) which enabled the development of efficient, sustainable and green procedures for azide-alkynes-cycloaddition (AAC) reactions, C-S coupling, O-allylation of phenol, Heck-type reactions and hydration of nitriles.
- Nasir Baig,Varma, Rajender S.
-
p. 398 - 417
(2013/03/14)
-
- A recyclable ruthenium(ii) complex supported on magnetic nanoparticles: A regioselective catalyst for alkyne-azide cycloaddition
-
A magnetically separable ruthenium catalyst was synthesized through immobilizing a pentamethylcyclopentadienyl ruthenium complex on iron oxide nanoparticles. The catalyst is highly active and selective for the synthesis of 1,5-disubstituted 1,2,3-trizoles
- Wang, Dong,Salmon, Lionel,Ruiz, Jaime,Astruc, Didier
-
supporting information
p. 6956 - 6958
(2013/09/02)
-
- Solvent-free Huisgen cyclization using heterogeneous copper catalysts supported on chelate resins
-
Copper catalysts supported on chelate resins bearing iminodiacetate moieties (DIAION CR11) or polyamine moieties (DIAION CR20) as chelating functional groups (12% Cu/CR11 and 7% Cu/CR20, respectively) were developed. 12% Cu/CR11 effectively catalyzed the
- Monguchi, Yasunari,Nozaki, Kei,Maejima, Toshihide,Shimoda, Yutaka,Sawama, Yoshinari,Kitamura, Yoshiaki,Kitade, Yukio,Sajiki, Hironao
-
p. 490 - 495
(2013/03/14)
-
- A new method for the synthesis of 1,5-disubstituted 1,2,3-triazoles via triazolium salt intermediates
-
A new transition metal free procedure for the synthesis of 1,5-disubstituted 1,2,3-triazoles, which proceeds via a triazolium salt intermediate is described. Georg Thieme Verlag KG Stuttgart · New York.
- Koguchi, Shinichi,Izawa, Kazuki
-
p. 3603 - 3608
(2013/02/21)
-
- Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition
-
Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.
- R?hrig, Ute F.,Majjigapu, Somi Reddy,Grosdidier, Aurélien,Bron, Sylvian,Stroobant, Vincent,Pilotte, Luc,Colau, Didier,Vogel, Pierre,Van Den Eynde, Beno?t J.,Zoete, Vincent,Michielin, Olivier
-
scheme or table
p. 5270 - 5290
(2012/08/28)
-
- Coordinatively unsaturated ruthenium complexes as efficient alkyneazide cycloaddition catalysts
-
The performance of 16-electron ruthenium complexes with the general formula Cp*Ru(L)X (in which L = phosphine or N-heterocyclic carbene ligand; X = Cl or OCH2CF3) was explored in azidealkyne cycloaddition reactions that afford the 1,2,3- triazole products
- Lamberti, Marina,Fortman, George C.,Poater, Albert,Broggi, Julie,Slawin, Alexandra M. Z.,Cavallo, Luigi,Nolan, Steven P.
-
experimental part
p. 756 - 767
(2012/03/22)
-