1694-19-5Relevant articles and documents
Synthesis of magnetically recyclable Fe3O4@[(EtO)3Si–L1H]/Pd(II) nanocatalyst and application in Suzuki and Heck coupling reactions
Keypour, Hassan,Saremi, Shokoufeh Ghahri,Noroozi, Mohammad,Veisi, Hojat
, (2017)
A Pd(II) Schiff base complex as an efficient and highly heterogeneous catalyst was developed by immobilization of a palladium complex on the surface of modified Fe3O4 magnetite nanoparticles. These surface-modified nanoparticles were characterized using various techniques such as transmission electron microscopy, X-ray diffraction, thermogravimetric analysis, vibrating sample magnetometry, elemental analysis and Fourier transform infrared spectroscopy. The palladium catalyst exhibited efficient catalytic activity in Suzuki and Heck coupling reactions. This method has notable advantages such as excellent chemoselectivity, mild reaction conditions, short reaction times and excellent yields. The yields of the products were in the range 85–100%. Also, the nanocatalyst can be easily recovered with a permanent magnet and reused at least five times without noticeable leaching or loss of its catalytic activity. Copyright
Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions
Lau, Phei Li,Allen, Ray W. K.,Styring, Peter
, p. 2886 - 2897 (2013)
The palladium metal catalysed Heck reaction of 4-iodoanisole with styrene or methyl acrylate has been studied in a continuous plug flow reactor (PFR) using supercritical carbon dioxide (scCO2) as the solvent, with THF and methanol as modifiers.
Stereoselective Base-Catalyzed 1,1-Silaboration of Terminal Alkynes
Gu, Yiting,Duan, Yaya,Shen, Yangyang,Martin, Ruben
, p. 2061 - 2065 (2020)
A base-catalyzed reaction that enables stereoselective 1,1-silaboration of terminal alkynes is described. This method not only offers a new strategy to functionalize simple and readily accessible alkynes beyond 1,2-difunctionalization, but also provides a
New fragmentation and rearrangement reactions of the azetidine ring promoted by AlEt2Cl
Alcaide, Benito,Salgado, Nati R.,Sierra, Miguel A.
, p. 467 - 470 (1998)
Azetidines 6 prepared by AlH2Cl reduction of easily available β-lactams 5 react with AlEt2Cl in CH2Cl2 solution at room temperature to yield, through new fragmentation or rearrangement reactions of the azetidine ring, either, olefins 7 or bicyclic fused pyrrolidines 8, depending on the nature of the group bonded to C2 of the four membered ring.
[60]Fullerene-Based Pd(0) Complexes of Phosphorus Ylides as Efficient Nanocatalyst for Homo- and Heterogeneous Mizoroki–Heck Coupling Reactions
Sabounchei, Seyyed Javad,Hashemi, Ali,Hosseinzadeh, Marjan,Salehzadeh, Sadegh,Maleki, Farahnaz
, p. 2319 - 2331 (2017)
Abstract: This work reports the synthesis and catalytic properties of new mono- and bidentate palladium(0)-[60]fullerene complexes, prepared by reaction of α-keto stabilized phosphorus ylides [Ph2P(CH2)nPPh2=C(H)C(O)C6H4-p-R] (n = 1, R = Ph, NO2, (Y1, Y2); n = 2, R = Ph, NO2, (Y3, Y4)), C60 and Pd(dba)2 (dibenzylideneacetone (dba)). Two coordination modes were observed: bidentate P,C-coordinated in the case of [(η ?C60)Pd(κ2 ?Y1)] (1) and [(η2?C60)Pd(κ2?Y2)] (2) and monodentate P-coordinated for [(η2?C60)Pd(Y3)2] (3) and [(η2?C60)Pd(Y4)2] (4) complexes. All complexes have been fully characterized by 1H, 13C and 31P NMR spectroscopic methods and other conventional techniques such as IR, thermogravimetry, inductively coupled plasma optical emission spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy and transmission electron microscopy analysis. Also, the catalytic activity of [60]fullerene-based nanocatalyst 2 in homo- and heterogeneous Mizoroki–Heck coupling reactions of various aryl chlorides with styrene was evaluated. The results implied that the both reactions exhibit their beneficial aspects such as high activity for homogeneous catalysis and facile separation and reusability for heterogeneous one. Furthermore, DFT studies of geometry-optimized monodentate and bidentate structures for 1 and 3 were calculated at the BP86/LANL2DZ and B3LYP/LANL2MB levels of theory to understand the origin of the observed coordination modes. Graphical Abstract: [Figure not available: see fulltext.].
A macrocyclic Pd(II)-Ni(II) complex in Heck and Suzuki reactions
Mieczyńska, Ewa,Lisowski, Jerzy,Trzeciak, Anna M.
, p. 145 - 149 (2015)
A heterodinuclear Pd(II)-Ni(II) macrocyclic Schiff base complex was applied as a catalyst for Heck and Suzuki cross-coupling reactions. In reaction of 4-bromoanisole with styrene, 4-methoxy-trans-stilbene was formed as the main product with a yield of up to 87%. In the Suzuki coupling of 4-bromoanisole with PhB(OH)2in a 2-propanol/water solution, up to 96% of the product was obtained. Analyses of the post-reaction mixtures confirmed the high stability of the macrocyclic Pd(II)-Ni(II) complex under the reaction conditions. The partial decomposition of the complex started at the Ni(II) site.
Development of Hierarchical Polymer@Pd Nanowire-Network: Synthesis and Application as Highly Active Recyclable Catalyst and Printable Conductive Ink
Mir, Sajjad Husain,Ochiai, Bungo
, p. 213 - 218 (2016)
A facile one-pot approach for preparing hierarchical nanowire-networks of hollow polymer@Pd nanospheres is reported. First, polymer@Pd hollow nanospheres were produced through metal-complexation-induced phase separation with functionalized graft copolymer
Oxadiazoline and ketoimine palladium(II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reactions in supercritical carbon dioxide
Fernandes, Ricardo R.,Lasri, Jamal,DaSilva, M. Fatima C. Guedes,Palavra, Antonio M. F.,Dasilva, Jose A. L.,Dasilva, Joao J. R. Frausto,Pombeiro, Armando J. L.
, p. 1153 - 1160 (2011)
The [2+3] cycloaddition of nitriles (RCN) with 2,2-dimethyl-3,4-dihydro-2H- pyrrole 1-oxide, in the presence of palladium dichloride (PdCl2) gives the corresponding 2,3-dihydro[1.2.4]oxadiazole (Δ4-1,2,4- oxadiazoline) palladium(II)
Imidazole, pyrimidine and diazepine containing heteroaryl-substituted heterocyclic salts as efficient ligand precursors for Mizoroki-Heck coupling reaction: Synthesis, structural characterization and catalytic activities
G?k, Yetkin,Akko, Senem,Akkurt, Mehmet,Tahir, Muhammad Nawaz
, p. 1767 - 1774 (2014)
The nine new heteroaryl-substituted imidazolidinium (1a-c), pyrimidinium (2a-c) and diazepinium (3a-c) salts as N-heterocyclic carbene (NHC) precursors were synthesized in good yields and entirely characterized using elemental analyses and conventional sp
Synthesis, characterization of N-heterocyclic carbene metallacrown palladium complex and catalytic activities in Suzuki and Heck coupling reaction
Wang, Jun-Wen,Gao, Lin-Ying,Meng, Fan-Hui,Jiao, Jing,Ding, Ling-Yan,Zhang, Li-Fang
, p. 119 - 128 (2012)
A series of new N-heterocyclic carbene Metllacrown palladium complexes with a highly flexible polyether-bridged chain (CH2OCH2) n (n = 1-3) have been synthesized by the reaction of the corresponding silver complexes and PdCl2(CH3CN) 2 in acetonitrile. Complexes 7a,b-9a,b have been structurally characterized. A single-crystal X-ray study of palladium complex 1,1-(oxy-1,2-ethanediyl)bis[3-(1-naphthalenemethyl) imidazol-2-ylidene] palladium hexafluorophosphate 7a adopt a cis configuration. They exhibited excellent catalytic activity in Suzuki-Miyoura and Heck coupling of aryl bromide in the presence of KOH. Graphical abstract: A series of new N-heterocyclic carbene metallacrown palladium (II) complexes have been synthesized. These palladium complexes show excellent catalytic activity in Suzuki and Heck coupling reaction.[Figure not available: see fulltext.]
Palladium and Bimetallic Palladium-Nickel Nanoparticles Supported on Multiwalled Carbon Nanotubes: Application to Carbon-Carbon Bond-Forming Reactions in Water
Ohtaka, Atsushi,Sansano, José M.,Nájera, Carmen,Miguel-García, Izaskun,Berenguer-Murcia, ángel,Cazorla-Amor?s, Diego
, p. 1841 - 1847 (2015)
Palladium and bimetallic Pd-Ni nanoparticles (NPs) protected by polyvinylpyrrolidone were prepared by the reduction-by-solvent method and deposited on multiwalled carbon nanotubes (MWCNTs). The catalytic activity of these NPs to carbon-carbon bond-forming reactions was studied by using 0.1 mol% Pd loading, at 120°C for 1 h and water as a solvent under ligand-free conditions. The Suzuki-Miyaura reaction took place quantitatively for the cross-coupling of 4-bromoanisole with phenylboronic acid, better than those obtained with potassium phenyltrifluoroborate, with Pd50Ni50/MWCNTs as a catalyst and K2CO3 as a base and TBAB as an additive, with good recyclability during 4 cycles with some Ni leaching. The Hiyama reaction of 4-iodoanisole with trimethoxyphenylsilane, under fluoride-free conditions using 50% aqueous NaOH solution, was performed with Pd/MWCNTs as a catalyst in 83% yield with low recyclability. For the Mizoroki-Heck reaction 4-iodoanisole and styrene gave the corresponding 4-methoxystilbene quantitatively with Pd50Ni50/MWCNTs using K2CO3 as a base and TBAB as an additive although the recycle failed. In the case of the Sonogashira-Hagihara reaction, Pd/MWCNTs had to be used as a catalyst and pyrrolidine as a base for the coupling of 4-iodoanisole with phenylacetylene under copper-free conditions. The corresponding 4-methoxytolane was quantitatively obtained allowing the recycling of the catalyst during 3 cycles. From black to green: The catalytic activity of palladium and bimetallic Pd-Ni nanoparticles deposited on multiwalled carbon nanotubes as a catalyst for cross-coupling reactions in water under ligandless conditions is disclosed. These reaction conditions represent an environmentally friendly alternative to those previously reported for reactions in organic solvents.
Synthesis and microwave-assisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenylmoieties in heck and suzuki cross-coupling reactions
Yilmaz, Uelkue,Sireci, Nihat,Deniz, Selma,Kuecuekbay, Hasan
, p. 414 - 420 (2010)
A mixture of bis-benzimidazole salts (1-7), Pd(OAc)2 and K 2CO3 in DMF - H2O catalyzes, in high yield, the Suzuki and Heck cross-coupling reactions assisted by microwave irradiation in a short time. In particular, the yields of the Heck and Suzuki reactionswith aryl bromideswere found to be nearly quantative. The synthesized bis-benzimidazole salts (1-7) were identified by 1H-13C NMR, IR spectroscopic methods and micro analysis. Copyright
Phosphine-Functionalized Chitosan Microparticles as Support Materials for Palladium Nanoparticles in Heck Reactions
Biajoli, André F. P.,Fajardo, André R.,Lemos, Thalia S. A.,de Souza, Jaqueline F.
, (2022/01/11)
Herein, we investigated the activation and stabilization of Pd nanoparticles using microparticles of chitosan-functionalized with phosphine moieties. The catalytic activity of the prepared material was assessed in a series of Heck reactions, which demonst
Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes
Zhang, Kena,Provot, Olivier,Alami, Mouad,Tran, Christine,Hamze, Abdallah
, p. 1249 - 1261 (2022/02/07)
This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis
Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
Kumaki, Wataru,Kinoshita, Hidenori,Miura, Katsukiyo
, (2022/03/07)
Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.
