80221-14-3Relevant academic research and scientific papers
Stereo- and regioselective gold(i)-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines
Cacchi, Sandro,Fabrizi, Giancarlo,Fochetti, Andrea,Ghirga, Francesca,Goggiamani, Antonella,Iazzetti, Antonia
supporting information, p. 527 - 532 (2019/01/24)
The gold-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines affords stereoselectively Z-enamine products with excellent regioselectivity. The reaction proceeds with moderate to excellent yields and accommodates a diverse range of functional groups on alkynes (ether, bromo, trifluoromethyl, acetyl, and carbomethoxy) and anilines (ether, bromo, chloro, and carbethoxy). The stereochemistry of the obtained enamines is complementary to that reported in previous studies. A plausible explanation for the observed selectivity was attained by means of NMR experiments.
Visible-light induced copper(i)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes
Charpe, Vaibhav Pramod,Hande, Aniket A.,Sagadevan, Arunachalam,Hwang, Kuo Chu
supporting information, p. 4859 - 4864 (2018/11/21)
Visible light mediated copper catalysed denitrogenative oxidative coupling of 2-hydrazinopyridines with terminal alkynes to form 2-(alkyl/arylethynyl) pyridines in the presence of O2 at room temperature is reported with 42 examples. This is the first report on visible light stimulated N2 elimination by an in situ generated copper(ii) superoxo/peroxo complex. N2 and water are the only by-products. The green chemistry metrics evaluation signifies that the current method is ecofriendly and economically feasible. This method allows the green synthesis of mGluR5 receptor antagonists, 2-methyl-6-(phenylethynyl)pyridine (MPEP) and 2-((3-methoxyphenyl)ethynyl)-6-methylpyridine (M-MPEP).
Sonogashira couplings catalyzed by collaborative (N-heterocyclic carbene)-copper and -palladium complexes
Gallop, Christopher W. D.,Chen, Ming-Tsz,Navarro, Oscar
supporting information, p. 3724 - 3727 (2014/08/05)
A general protocol for the Sonogashira reaction using a 100:1 combination of (N-heterocyclic carbene)-Cu and (N-heterocyclic carbene)-Pd complexes is presented. Catalyst loadings of 1 mol % (NHC)-Cu and 0.01 mol % (NHC)-Pd allow for the coupling of aryl bromides and aryl alkynes, in air and in a non-anhydrous solvent, in high yields.
Dimethylaminoalkyl chalcogenolate palladium(II) complexes as an efficient copper-and phosphine-free catalyst for Sonogashira reaction
Khairnar, Bhikan J.,Dey, Sandip,Jain, Vimal K.,Bhanage, Bhalchandra M.
supporting information, p. 716 - 719 (2014/01/23)
N,N-Dimethylaminoalkyl chalcogenolate Pd(II) complexes [PdCl(E a∩NMe2)]n has been investigated as a moisture/air-stable and robust catalyst for Sonogashira cross-coupling reaction in the absence of copper and phosphine ligand. The dimeric palladium(II) complex of selenium containing ligand shows the best catalytic activity as compared with monomeric and trimeric complexes. The variety of functional groups are tolerated under optimized catalytic systems and provide excellent yields of the products.
Palladium nanoparticles supported on natural nanozeolite clinoptilolite as a catalyst for ligand and copper-free C-C and C-O cross coupling reactions in aqueous medium
Baghbanian, Seyed Meysam,Yadollahy, Horieh,Tajbakhsh, Mahmood,Farhang, Maryam,Biparva, Pourya
, p. 62532 - 62543 (2015/02/19)
In this article, Pd0-nanoparticles supported on natural nanozeolite clinoptilolite (CP) were successfully synthesized, and the catalytic activity of the nanocatalyst was investigated in C-C and C-O coupling reactions, namely the Sonogashira and Ullmann condensation reactions in an aqueous medium. The nanocatalyst was characterized by various techniques such as powder-XRD, BET, SEM, TEM, HRTEM, TEM-EDS, ICP-OES and XPS. From an electron microscopy (SEM) study it can be inferred that the particles are mostly spherical or of ellipsoidal shape and have diameters ranging from 25 to 80 nm. A HRTEM study reveals that Pd0-nanoparticles supported on nanozeolite CP have an average diameter of ～10 nm. The supported palladium nanoparticles showed excellent catalytic activity in the synthesis of aryl alkynes and diaryl ethers in high yields. In addition, the nanocatalyst could be recycled and reused several times without significant loss of catalytic activity.
Palladium-poly(3-aminoquinoline) hollow-sphere composite: Application in sonogashira coupling reactions
UlIslam, Rafique,Mahato, Sanjit K.,Shukla, Sudheesh K.,Witcomb, Michael J.,Mallick, Kaushik
, p. 2453 - 2461 (2013/08/23)
We report on the use of palladium acetate for the synthesis of a palladium-based polymer composite material as a catalyst for Sonogashira cross-coupling reactions for aryl and heteroaryl of iodides and bromides.
N-heterocyclic carbene adducts of cyclopalladated ferrocenylchloropyrimidine: Synthesis, structural characterization and application in the Sonogashira reaction
Xu, Chen,Lou, Xin-Hua,Wang, Zhi-Qiang,Fu, Wei-Jun
, p. 519 - 523 (2012/10/29)
Three N-heterocyclic carbene (NHC) adducts of cyclopalladated ferrocenylchloropyrimidine, 2-4 [PdCl{[(n5-C5H 5)]Fe[(n5-C5H3)-N2C 4H2-Cl]}(NHCs)] have been prepared by reaction of the chloride-bridged palladacyclic dimer 1 [PdCl{[(n5-C5H 5)]Fe[(n5-C5H3)-N2C 4H2-Cl]}]2 with the corresponding imidazolium salts. These complexes were characterized by elemental analysis, IR, ESI-MS and NMR. The use of these complexes as catalysts for the Sonogashira reaction was examined. Complex 4 proved to be an efficient catalyst for the Sonogashira reaction of aryl bromides and some activated aryl chlorides under copperand amine-free conditions. Typically, using 0.1-2 mol % of catalyst in the presence of 1.5 equivalents of CsOAc as base in dimethylacetamide at 120 °C provided coupling products in good yields. Springer Science+Business Media B.V. 2012.
[Cu(acac)2]·H2O-catalyzed sonogashira-type couplings of aryl halides and terminal alkynes
Li, Tingyi,Qu, Xiaoming,Xie, Guanlei,Mao, Jincheng
experimental part, p. 1325 - 1330 (2012/06/04)
Highly selective coupling of aryl halides with terminal alkynes can be conducted using low-cost and readily available [Cu(acac)2] ·H2O under palladium- and amine-free conditions. This protocol makes the typical Sonogashira reaction more practical and useful (TBAB=tetrabutyl ammonium bromide; DMSO=dimethyl sulfoxide; see scheme). Copyright
Nitrogen heteroaromatic cations by [2+2+2] cycloaddition
Cikova, Martina,Kolivoska, Viliam,Cisarova, Ivana,Saman, David,Pospisil, Lubomir,Teply, Filip
supporting information; experimental part, p. 450 - 462 (2011/02/28)
A modular approach to the construction of monocationic quaternary N-heteroaromatic frameworks was developed capitalizing on a direct pyridine-type nitrogen quaternization followed by metal-catalyzed [2+2+2] cycloaddition with gaseous acetylene. The flexib
Highly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides
Lee, Dong-Hwan,Jung, Ji-Young,Jin, Myung-Jong
experimental part, p. 2024 - 2029 (2011/02/22)
Silica gel-supported β-ketoiminatophosphane-Pd complex (Pd@SiO 2) was shown to be a highly active and long-lived catalyst for aqueous Suzuki, Stille and Sonogashira coupling reactions of heteroaryl chlorides. A wide range of heteroaryl chlorides could be efficiently coupled with different nucleophilic partners in the presence of only 0.5 mol% catalyst and under mild conditions. This is one of the most powerful heterogeneous catalysts for the couplings of diverse heteroaryl chlorides. Furthermore, the catalyst could be reused with almost consistent activity. The Royal Society of Chemistry 2010.
