92-91-1Relevant articles and documents
Molecular structures and catalytic activity of palladium complexes derived from lutidine-bridged bis(benzimidazolin-2-ylidene) ligands
Jahnke, Mareike C.,Pape, Tania,Hahn, F. Ekkehardt
, p. 357 - 361 (2007)
Reaction of lutidine-bridged dibenzimidazolium dibromides 1-4 with palladium acetate gives pincer-type palladium complexes of the type [Pd(L)Br]Br [5]Br-[8]Br. Crystals suitable for an X-ray diffraction study have been obtained by slow evaporation of the solvent from dichloromethane/methanol solutions of [7]Br and [8]Br. The crystal structure of [7]+ reveals a pincer topology of the cationic complex with a distorted square-planar coordination geometry at the metal center. From a solution of complex [8]Br, a dinuclear byproduct [9]+ was obtained with two bis(benzimidazolin2-ylidene) ligands coordinating in a bridging fashion. The pincer-type palladium complexes [5]Br[8]Br were tested as precatalysts in Suzuki coupling reactions.
Synthesis, characterization, theoretical calculations and enzymatic activities of novel diimine-dioxime ligand and its homodinuclear Cu(II) complex
Dede, Bülent,?zen, Nurten,G?rgülü, Güven?
, p. 357 - 367 (2018)
A novel ligand [2-(biphenyl-4-yl)-2-(2-(1-(biphenyl-4-yl)-2-(hydroxyimino) ethylideneamino)ethylimino)acetaldehyde oxime] (BPHEO) and its homodinuclear Cu(II) complex [Cu2(L) (H2O) (phen)](ClO4)2 were prepared starting from biphenyl and characterized by different physical techniques. Elemental analysis, ICP-OES, FT-IR, UV–vis molar conductivity, magnetic moment measurements and thermal analyses studies were used for the characterization of the complexes. The free ligand was also characterized by 1H and 13C NMR spectra. Elemental analyses, stoichiometric and spectroscopic data of the metal complex indicated that the metal:ligand ratio of homodinuclear Cu(II) complex was found to be 2:1. The structural and vibrational spectroscopic data of the BPHEO and its homodinuclear Cu(II) complex were calculated and confirmed by DFT method. Chemical shifts (1H and 13C NMR) of the ligand were also calculated using the gauge-independent atomic orbital (GIAO) method. Furthermore the synthesized complex was tested as catalyst for the catalytic oxidation of 3,5-di-tert-butylcatechol to 3,5-di-tert-butylquinone at aerobic medium (catecholase-like activity) and disproportionation of hydrogen peroxide to the water and molecular oxygen in the presence of 1-methylimidazole (catalase-like activity). It was found that the complex showed moderate catalytic activity and suitable as a catalyst for the selected enzymatic reactions.
The synergistic effect of cobalt on a Pd/Co catalyzed Suzuki-Miyaura cross-coupling in water
You, Li-Xin,Liu, Hui-Jie,Cui, Lan-Xin,Ding, Fu,Xiong, Gang,Wang, Shu-Ju,Ren, Bao-Yi,Dragutan, Ileana,Dragutan, Valerian,Sun, Ya-Guang
, p. 18455 - 18458 (2016)
This work introduces the new trimetallic complex CoPd2(HBPDC)2Cl4·(H2O)4(H2BPDC = 2,2′-bipyridine-4,4′-dicarboxylic acid) as a highly efficient and more cost-effective catalyst for a Suzuki-Miyaura reaction proceeding in water, without additives and under aerobic conditions. Catalytic studies revealed a synergistic Co-Pd cooperativity, fostered by ligation through H2BPDC, and accounting for the superior performance of the heterobimetallic complex vs. its Co-free counterpart.
Hybrid organic-inorganic silica materials containing di(2-pyridyl)methylamine-palladium dichloride complex as recyclable catalysts for Suzuki cross-coupling reactions
Trilla, Montserrat,Pleixats, Roser,Man, Michel Wong Chi,Bied, Catherine,Moreau, Joeel J. E.
, p. 2399 - 2403 (2006)
High surface hybrid silica materials containing di(2-pyridyl)methylamine-palladium dichloride complex covalently bonded to the silica matrix were prepared by sol-gel process and successfully tested as reusable catalysts for Suzuki cross-coupling reactions.
(NHC)-Pd(II) complexes with hydrophilic nitrogen ligands: Catalytic properties in neat water
Tuerkmen, Hayati,Goek, Luetfiye,Kani, Ibrahim,Cetinkaya, Bekir
, p. 633 - 642 (2013)
The cleavage reactions of the dimers [(NHC)PdX2]2 with hydrophilic N-donors, L, afforded the mixedligand complexes of the type trans-[(NHC)LPdX2] (X = Cl or Br; NHC = 1,3-dialkylbenzimidazol-2- ylidene (BIm) or bis(imino)a
Synthesis of a porphyrinic polymer for highly efficient oxidation of arylalkanes in water
Zou, Chao,Zhao, Min,Wu, Chuan-De
, p. 116 - 120 (2015)
A highly stable covalent-porphyrinic framework Mn-CPF-1 was synthesized by reaction of cyanuric chloride and tetraphenylamine porphyrin (TAPP) and subsequent metallation. Mn-CPF-1 exhibits remarkable catalytic activity and stability on catalytic oxidation of arylalkanes in water under mild conditions, which is much superior to the homogeneous analog Mn-tetraphenylporphyrin (Mn-TPP) under identical conditions.
Striking dual functionality of a novel Pd?Eu-MOF nanocatalyst in C(sp2)-C(sp2) bond-forming and CO2fixation reactions
Ding, Fu,Dragutan, Ileana,Dragutan, Valerian,Liu, Xue-Gui,Sun, Ya-Guang,Xiong, Gang,Yao, Shan-Xin,You, Li-Xin,Zhao, Bai-Bei
, p. 6368 - 6376 (2020)
Pd nanoparticles were immobilized on a highly porous, hydrothermally stable Eu-MOFviasolution impregnation and H2reduction to yield a novel Pd?Eu-MOF nanocatalyst. This composite was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive spectroscopy (EDS), inductively coupled plasma optical emission spectroscopy (ICP-OES), powder X-ray diffraction (PXRD) and X-ray photoelectron spectroscopy (XPS). Unprecedentedly, the Pd?Eu-MOF nanocatalyst could be applied with excellent results in two strikingly different, mechanistically distinct, reactionsi.e., Suzuki-Miyaura cross-coupling and cycloaddition of CO2to a range of epoxides. Under the best reaction conditions, 98-99% yields have been attained in both catalytic processes. Moreover, in either case the heterogeneous catalyst was easily recovered and efficiently reused for more than four cycles, indicating its high stability and reproducibility. PXRD, TEM and XPS measurements on the recycled catalyst confirmed that it maintained its original structure and morphology; no Pd NP agglomeration was observed.
Palladium and platinum complexes of the new ligands containing P-N and P-O bonds
Iri?li, Sevil,Karaman, Merve,Arda, Nilgün,Dindar, Bircan,Büyükgüng?r, Orhan
, p. 203 - 209 (2014)
A number of applications have been found for the variety complexes of Pd(II) and Pt(II) due to their marked catalytic activities. This study is intended to examine the seven and eight-membered novel complexes which have been prepared by P-N-C-C-O-P and P-
Catalytic activity of k3-X,N,Y-palladium pincer complexes (X, y = O, S) with (thio)phosphoryl-substituted carbamoylmethylphosphine oxide and sulfide ligands in the Suzuki cross-coupling
Vasil'Ev, Andrei A.,Aleksenko, Valentina Yu.,Aleksanyan, Diana V.,Kozlov, Vladimir A.
, p. 344 - 346 (2013)
Palladium pincer complexes with N-{2-[diphenyl(thio)phosphoryl]phenyl} carbamoylmethylphosphine oxide and sulfide ligands provide moderate activity in the Suzuki cross-coupling.
Superb efficient and recycle polymer-anchored systems for palladium catalyzed Suzuki cross-coupling reactions in water
Siga, Fatma,Temel, Hamdi,Aydemir, Murat,Ocak, Yusuf Selim,Pasa, Salih,Baysal, Akin
, p. 172 - 182 (2012)
A set of three new polymer-anchored palladium(II) Schiff base catalysts have been synthesized, characterized and their catalytic activity was investigated in the Suzuki cross-coupling reaction between aryl halides and arylboronic acid in the presence of Cs2CO3 as a base. They show excellent catalytic activity in coupling of aryl bromides or aryl iodide with phenylboronic acid under the optimized reaction conditions in water. Polymer-anchored Pd(II) complexes provided turnover frequency of 29,700 or 58,200 h-1 in Suzuki coupling reactions of phenylboronic acid with p-bromoacetophenone or p-iodobenzene, respectively, which are the highest values ever reported for the Suzuki coupling reactions in water as sole solvent. The catalyst 1 could be used for 15 reaction cycles in the Suzuki coupling of p-acetobromobenzene at 100 °C with no loss of catalytic activity.
Supramolecular immobilization of a perfluoro-tagged Pd-catalyst with dendritic architectures and application in Suzuki reactions
Garcia-Bernabe, Abel,Tzschucke, Carl Christoph,Bannwarth, Willi,Haag, Rainer
, p. 1389 - 1394 (2005)
A new supramolecular complex of a perfluoro-tagged palladium phosphine catalyst to a dendritic core-shell architecture with a perfluoroalkyl shell was used as recoverable catalyst for Suzuki couplings. This homogeneous complex can also serve as a model for related catalysts adsorbed on fluorous silica gel.
Engineering functional group decorated ZIFs to high-performance Pd@ZIF-92 nanocatalysts for C(sp2)-C(sp2) couplings in aqueous medium
You, Li-Xin,Zhao, Bai-Bei,Yao, Shan-Xin,Xiong, Gang,Dragutan, Ileana,Dragutan, Valerian,Ding, Fu,Sun, Ya-Guang
, p. 80 - 87 (2020)
Herein the first ever Pd2+-decorated ZIF-92 nanostructure is readily accessed by post-synthesis modification (PSM) of the zeolitic imidazolate framework ZIF-90. Thus, the imidazolate linker of the ZIF-90 is functionalized with the hydroxyethylimino group, followed by anchoring the palladium catalytically active sites through a tight coordination of Pd2+ ions to both the N and O atoms of ZIF-92. The acquired data (by PXRD, EDS, SEM, XPS, ICP-AES) concerning the crystalline structure, elemental mapping and network configuration of the Pd@ZIF-92 catalyst confirmed its structure, before and after the cross-coupling reactions and following recycling. The Pd@ZIF-92 showed excellent catalytic activity (>99%) and chemoselectivity in Suzuki-Miyaura coupling proceeding in neat water, at very low Pd loading (0.009 mol%). Comparison of its performance with that of many reported Pd nanocatalysts operating in aqueous/protic media testifies to its superiority. The appealing gateway to this innovative, stable, robust, easily recoverable and reusable Pd@ZIF-92 nanostructure recommends its beneficial utilization in C(sp2)-C(sp2) cross-couplings and other sustainable, environmentally-friendly processes.
An efficient clean and sustainable methodology for catalytic C-C coupling process over a Pd-free magnetically recoverable cobalt catalyst
Masteri-Farahani, Majid,Niakan, Mahsa
, (2022/03/27)
The Suzuki and Sonogashira coupling reactions are important processes in organic synthesis. However, to date, these reactions have been extensively examined using Pd-based catalysts in toxic organic solvents. Therefore, developing clean and inexpensive methodologies for these reactions remained a major challenge. Herein, by taking the advantages of thiol-ene click reaction, an easy and robust strategy for surface modification of magnetic graphene oxide with a dendrimer structure was successfully developed. Dendrimer-functionalized magnetic graphene oxide was then applied for the immobilization of Co nanoparticles. Transmission electron microscopy exhibited a homogeneous distribution of Co nanoparticles with the size of about 3 nm. The resultant nanocomposite revealed high efficiency in catalytic Suzuki and Sonogashira reactions in non-hazardous and sustainable deep eutectic solvents (DESs). The DES and catalyst were simply recycled five times with gradual slight decrease in the yield of the reactions. More importantly, the catalyst was magnetically isolated at the end of the recycling process. Overall, the utilization of DES as an environmentally friendly and recoverable reaction medium, as well as replacing the low-cost cobalt catalyst as an alternative to expensive Pd catalyst along with the facile catalyst isolation by employing an external magnetic field, make the present protocol promising from economic and green chemistry points of view for the clean C-C coupling reactions.
Palladium(ii) complexes of 2,2′-tellurobis(: N, N -diphenyl acetamide): Efficient catalysts for Suzuki-Miyaura coupling at room temperature under air
Singh, Ajai K.,Singh, Poornima
, p. 966 - 973 (2022/02/07)
Three complexes, [Pd(L2)2Br2] (C1), [(L2)PdCl(μ-Cl)2PdCl(L2)] (C2), and [Pd(L2)PPh3Cl2](C3) of a tellurium ligand, 2,2′-tellurobis(N,N-diphenylacetamide) ((Ph2NCOCH2)2Te = L2), reported here catalyze Suzuki-Miyaura coupling efficiently at room temperature under aerobic conditions, and the optimum loading of the catalyst is 0.001 mol% of Pd. Oxidative addition of elemental tellurium to 2-bromo-N,N-diphenylacetamide results in bis(N,N-diphenylamidomethyl)tellurium(iv) dibromide ((Ph2NCOCH2)2TeBr2) (L1). The reduction of L1 with aqueous bisulfite results in (Ph2NCOCH2)2Te(= L2). The complexes C1 and C2 were obtained by the reactions of L1 and L2 with Na2PdCl4 at room temperature in dichloromethane and ethanol, respectively. The complex C2 on reaction with triphenylphosphine results in C3. L1, L2, C1, C2, and C3 were characterized by HR-MS, 1H, 13C{1H} and 125Te{1H} NMR and IR spectra. The single crystal structures of all these compounds were determined by X-ray diffraction. The geometry of Pd in all the complexes, C1-C3, is nearly square planar. The scope of C1-C3 for catalysis of Suzuki-Miyaura coupling is reported.
