2920-38-9Relevant articles and documents
Vink et al.
, p. 710 (1972)
PVP-stabilized palladium nanoparticles electrochemically obtained as effective catalysts in aqueous medium Suzuki-Miyaura reaction
Uberman, Paula M.,Martin, Sandra E.,Perez, Luis A.,Lacconi, Gabriela I.
, p. 245 - 253,9 (2012)
In this paper the synthesis of stable palladium nanoparticles (PdNPs) by electrochemical methods at room temperature is reported. Direct electroreduction of H2PdCl4 aqueous solution in the presence of poly-(N-vinyl-2-pirrolydone) (PVP) onto platinum electrodes was performed by the application of a constant current density pulse. By simultaneous stirring of the electrolyte, the NPs formed on the electrode surface were stabilized with PVP in the solution. The resulting PdNPs were characterized by transmission electron microscopy and the total content of palladium was analytically determined by atomic absorption measurements. The average size of the NPs (in the range of 10-22 nm) was tuned by changing the current density applied. The PdNPs prepared by this methodology exhibited highly efficient catalytic activity on Suzuki-Miyaura coupling reaction in aqueous medium. Particularly high turnover numbers (TON up to 104-105) were achieved by these PVP-stabilized PdNPs with aryl iodides and bromides.
Fe3O4@SiO2@ l -arginine@Pd(0): A new magnetically retrievable heterogeneous nanocatalyst with high efficiency for C-C bond formation
Ghorbani-Choghamarani, Arash,Azadi, Gouhar
, p. 247 - 252 (2016)
The surface of Fe3O4@SiO2 nanoparticles was modified using l-arginine as a green and available amino acid to trap palladium nanoparticles through a strong interaction between the metal nanoparticles and functional groups of the amino acid. The proposed green synthetic method takes advantage of nontoxic reagents through a simple procedure. Characterization of Fe3O4@SiO2@l-arginine@Pd(0) was done using Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, vibrating sample magnetometry and inductively coupled plasma analysis. The catalytic activity of Fe3O4@SiO2@l-arginine@Pd(0) as a new nanocatalyst was investigated in C-C coupling reactions. Waste-free, use of green medium, efficient synthesis leading to high yield of products, eco-friendly and economic catalyst, excellent reusability of the nanocatalyst and short reaction time are the main advantages of the method presented.
LIQUID CRYSTALLINE 4-ALKYLAMINO-4 prime -CYANOBIPHENYLS.
Ruoliene,Adomenas,Tubelyte,Seskauskas,Grozhik
, p. 211 - 216 (1981)
A number of mesomorphic 4-alkylamino-4 prime -alkylamino-4 prime -cyanobiphenyls were synthesized. These compounds melt at higher temperatures and form nematic and smectic. A state with higher thermal stability than that of analogaous 4-alkoxy-4 prime -cyanobiphenyls. 4-Octylamino-4 prime -cyanobiphenyl is characterized by a significantly higher dielectric anisotropy in comparison with its 4-octyloxy analog, in the nematic state, but not in the smectic state. Density data and refractometric indices of several 4 substituted 4 prime -cyanobiphenyls are presented; refractometric data confirm higher polarizability of 4-alkylamino-4 prime -cyanobiphenyls as compared with their 4-alkoxy analogs.
Effect of Alkyl Structures on the Anti-stacking and Anchoring of Pd/Diamine-Functionalized Graphene Nanoparticles in Application in Suzuki Reaction
Tian, Yinbing,Tang, Zijie,Ru, Yu,Wang, Yuanyuan,Dai, Liyi
, p. 2745 - 2754 (2021)
Three diamines (1,8-diaminooctane/p-phenylenediamine/biphenylenediamine) with different alkyl groups were used to synthesize the functionalized graphene networks. Pd as the common metal catalyst was used to explore the effects of alkyl types of diamines on anti-stacking, metal anchoring ability of functional graphene and hence the catalytic performance. The results were discussed by characterization of the material and its catalytic properties. All catalysts showed excellent catalytic performance on the Suzuki cross-coupling reaction with a high yield of up to 100%. The p-phenylenediamine and biphenylenediamine functionalized graphene with larger specific surface area was beneficial to improve the stability of the graphene catalyst and maintain good catalytic activity after 5 cycles. The Pd nanoparticles in 1,8-octanediamine materials have smaller size and a smaller loading with the same or even better catalytic performance than p-phenylenediamine, biphenylenediamine materials, due to the stronger electron donating ability of N of octanediamine than that of p-phenylenediamine.
The recyclable cyclopalladated ferrocenylimine self-assembly catalytic film and investigation of its role in the mechanism of heterogeneous catalysis
Fu, Zhihua,Li, Tiesheng,He, Xiaohang,Liu, Jie,Wu, Yangjie
, p. 26413 - 26420 (2014)
An efficient, reusable and stable catalyst nano-sheet film (Si-CDI-Pd) was developed, in which cyclopalladated ferrocenylimines were grafted onto silicon, glass and quartz surfaces by covalent bonds. Water contact angle, ultraviolet-visible spectroscopy (UV-Vis), X-ray photoelectron spectroscopy (XPS), atomic force microscopy (AFM), low-angle X-ray diffraction (LAXD) and cyclic voltammetry (CV) were used to characterize the structural and compositional information of the modified surfaces. The immobilized catalyst films were tested for the Suzuki-Miyaura reaction and displayed high activity for the preparation of various biaryls at elevated temperatures in neat water without ligands. It also presented good stability and reusability. It can be reused at least 8 times with little Pd leaching into the crude product. The reasonable and feasible reaction mechanism of the heterogeneous Suzuki-Miyaura reaction based on the results of AFM, XPS, and CV tests of different reaction times were explored in detail, in which a cycle of PdII to Pd 0 and Pd0 to PdII on the surface was clearly detected and illustrated. In this approach, Pd0 on the surface of nano-sheet films as an active surface to catalyze the coupling reaction of aromatic halides and borophenylic acid proceeded via a mechanism of surface-catalyzed process.
A fluorous ethylenediamine promoted direct C-H arylation of unactivated arenes with aryl halides
Zhu, Yi-Wei,Shi, Yi-Xin
, p. 10 - 13 (2016)
A novel and recyclable fluorous ethylenediamine was prepared. Together with potassium tert-butoxide, the fluorous ethylenediamine showed a good activity in promoting the coupling of aryl halides with benzene derivatives without the aid of transition-metal catalysts. Furthermore, a chain homolytic aromatic substitution mechanism was proposed in this paper.
An efficient palladium and bis(2-pyridylmethyl)amine-based system for Suzuki-Miyaura cross-coupling under aqueous and aerobic condition
Yu, Jianjun,Wang, Limin,Liu, Mingtao,Qiu, Jun,Shen, Qiang,Fang, Lei,Tang, Jun
, p. 1114 - 1118 (2012)
A novel PdCl2/bis(2-pyridylmethyl)amine-based ligand (1) catalytic system, which is water-soluble and air-stable, has been successfully synthesized and applied for Suzuki-Miyaura cross-coupling reaction. In the presence of catalytic amount of PdCl2/1 system, arylboronic acids can couple with a wide range of aryl halides, including aryl bromides and aryl chlorides. The reactions proceed under mild conditions to give excellent yields, and a wide range of functionalities is tolerated.
(π-Allyl)Pd complexes containing N-heterocyclic carbene and pseudohalogen ligands - Synthesis, reactivity toward organic isothiocyanates and isocyanides, and their catalytic activity in suzuki-miyaura cross-couplings
Kim, Hyun-Kyung,Lee, Jung-Hyun,Kim, Yong-Joo,Nu Zheng, Zhen,Lee, Soon W.
, p. 4958 - 4969 (2013)
Dinuclear (π-allyl)palladium chlorides, [(π-allyl)Pd(μ-Cl)] 2, were cleaved by N-heterocyclic carbenes (NHCs) to give mononuclear (π-allyl)palladium-NHC chlorides, [(π-allyl)Pd(Cl)(NHC)] (1-6) [NHC = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPR), 1,3-bis(2,6- diisopropylphenyl)-4,5-dihydroimidazol-2-ylidine (SIPR), 1,3-bis(2,4,6- trimethylphenyl)imidazol-2-ylidene (IMes)]. Complexes 1-6 were subsequently treated with aqueous NaN3, KSCN, KOCN, and CF3COOAg to produce the corresponding mononuclear (π-allyl)palladium-NHC pseudohalogen complexes, [(π-allyl)Pd(X)(NHC)] (X = N3, NCS, SCN, NCO, CF 3COO) (7-30). These products could also be obtained by treating dinuclear pseudohalogen-bridged Pd complexes, [(π-allyl)Pd(μ-X)] 2, which were prepared by replacing the μ-Cl ligand in [(π-allyl)Pd(μ-Cl)]2, with aqueous NaN3, KSCN, KOCN, or CF3COOAg, followed by cleavage with the NHCs. Reactions of [(π-allyl)Pd(N3)(NHC)] with organic isothiocyanates (R-NCS) or CH3O(CO)C≡CO(CO)CH3 resulted in selective 1,3-dipolar cycloaddition into the Pd-azido bond to give heterocyclic compounds. By contrast, analogous reactions of [(η3-allyl)Pd(N 3)(IPr)] with an organic isocyanide (R-NC: R = tert-butyl, benzyl) gave the adduct [(η3-allyl)Pd(N3)(IPr)]·(R-NC) as the only product or a mixture of the adduct and a dipolar cycloaddition product, [(η3-allyl)Pd{CN4(R)}(IPr)], depending on the isocyanides used. Finally, a series of (π-allyl)Pd-NHC pseudohalogen complexes, [(π-allyl)Pd(X)(NHC)], exhibited high catalytic activity in Suzuki-Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids. A series of (π-allyl)palladium complexes containing N-heterocyclic carbene and pseudohalogen ligands are prepared and their reactivity toward organic isothiocyanates and isocyanides is studied. Suzuki-Miyaura cross-coupling reactions of aryl chlorides with aryl boronic acid catalyzed by these (π-allyl)palladium complexes are reported. Copyright
Functional group compatible palladium-catalyzed cross-coupling reactions between aryllithium and aryl halide mediated by a five-membered cyclic silyl ether
Son, Eun-Cheol,Tsuji, Hayato,Saeki, Tomoyuki,Tamao, Kohei
, p. 492 - 494 (2006)
A functional group compatible palladium-catalyzed cross-coupling reaction between aryllithiums and aryl halides mediated by a five-membered cyclic silyl ether as a precursor for an activated arylsilane has been developed. The reaction proceeds under mild conditions without the addition of a fluoride salt or a base to activate the silyl reagent.
Color-coded ligands: Tracking the catalyst using highly pigmented porphyrazine ligands in biphasic reactions
Tshivhase, Mmboneni,Williams, D. Bradley G.
, p. 7023 - 7026 (2015)
We demonstrate the concept that highly colored imidazolium porphyrazine ligands and complexes may be useful for visualizing the location of a catalyst and/or ligand. This was analytically demonstrated by the application of UV-vis spectrophotometry to detect the ligand and ICP-OES spectroscopy for quantification of the Pd in the biphasic systems. In the first instance, a toluene/water system was used, in which the complex and ligand preferred the organic phase. Water-soluble substrates were made to react under these conditions by employing the complexes as catalysts in Heck and Suzuki C-C bond forming reactions. In the second instance, an ionic liquid containing biphasic mixture was used, in which the ligand/catalyst was retained in the ionic liquid. Catalyst recycling experiments were met with limited success.
Sulfur-containing palladacycles: Efficient phosphine-free catalyst precursors for the Suzuki cross-coupling reaction at room temperature
Zim, Danilo,Gruber, Adriane S.,Ebeling, Gunter,Dupont, Jairton,Monteiro, Adriano L.
, p. 2881 - 2884 (2000)
Cyclopalladated compounds derived from the ortho-metalation of benzylic tert-butyl thioethers are excellent catalyst precursors for the Suzuki cross-coupling reaction of aryl bromides and chlorides with phenylboronic acid under mild reaction conditions. A broad range of substrates and functional groups are tolerated in this protocol, and highly catalytic activity is attained.
Ligandless C-C bond formation via Suzuki-Miyaura reaction in micelles or water-ethanol solution using PdPtZn and PdZn nanoparticle thin films
Hoseini, S. Jafar,Zarei, Atiyeh,Rafatbakhsh Iran, Hajar
, p. 489 - 494 (2015)
PdPtZn and PdZn nanoparticle (NP) thin films were synthesized by the reduction of [PdCl2(cod)], [PtCl2(cod)] (cod = cis,cis-1,5-cyclooctadiene) and [Zn(acac)2] (acac = acetylacetonate) complexes at an oil-water interface. The structure and morphology of the as-prepared NPs were characterized with X-ray diffraction, transmission electron microscopy and energy dispersive analysis of X-rays. Catalytic activity of the prepared NPs was investigated in the Suzuki-Miyaura cross-coupling reaction in H2O-EtOH and various micellar media systems such as cetyltrimethylammonium bromide (cationic surfactant), sodium dodecylsulfate (anionic surfactant) and Pluronic P123 (non-ionic surfactant). PdPtZn and PdZn thin films exhibited higher catalytic activity compared to Pd thin film in the Suzuki-Miyaura coupling reaction due to the appropriate interaction between palladium, platinum and zinc metals. PdPtZn and PdZn nanoparticle thin films were synthesized by the reduction of [PdCl2(cod)], [PtCl2(cod)] and [Zn(acac)2] complexes at an oil-water interface. Catalytic activity of the nanoparticles was investigated in Suzuki-Miyaura cross-coupling reactions in various micellar systems or water-ethanol solution.
Graphene oxide supported Au nanoparticles as an efficient catalyst for reduction of nitro compounds and Suzuki-Miyaura coupling in water
Fakhri, Parisa,Nasrollahzadeh, Mahmoud,Jaleh, Babak
, p. 48691 - 48697 (2014)
This paper reports on the synthesis of graphene oxide supported Au nanoparticles and their application as a separable catalyst for ligand-free Suzuki-Miyaura coupling reactions in water and reduction of nitro compounds. The catalyst was characterized using powder XRD, BET, FT-IR, Raman, SEM and EDS. This method has the advantages of high yields, simple methodology, and elimination of ligand, organic solvent and homogeneous catalysts and easy work up. Interestingly, the novel catalyst could be recovered in a facile manner from the reaction mixture and recycled several times without any significant loss of catalytic activity. This journal is
Bis-cyclopentadienyl nickel (Nickelocene): A convenient starting material for reactions catalyzed by Ni(O) phosphine complexes
Leadbeater
, p. 7539 - 7541 (2001)
-
-
Dahl,Lewis
, p. 1307 (1965)
-
Activation of aryl chlorides in water under phase-transfer agent-free and ligand-free Suzuki coupling by heterogeneous palladium supported on hybrid mesoporous carbon
Duan, Linlin,Fu, Rao,Xiao, Zhiguang,Zhao, Qingfei,Wang, Jian-Qiang,Chen, Shangjun,Wan, Ying
, p. 575 - 586 (2015)
In this study, heterogeneous palladium catalysts supported on ordered mesoporous cobalt oxide-carbon nanocomposites were applied to the water-mediated Suzuki coupling reaction of chlorobenzene and phenylboronic acid and exhibited a high yield of biphenyl (49%) under mild reaction conditions free of phase-transfer agents and ligands. Product yields in the reaction of aryl chlorides containing electron-withdrawing groups attached to their benzene ring can reach approximately 90%. Thiol-functionalized mesoporous silica, which can trap soluble Pd species, was used to confirm the negligible leaching in solution and therefore heterogeneous reaction. This heterogeneous catalyst is stable, showing unobvious activity loss after 10 catalytic runs. Characterization by X-ray diffraction, transmission electron microscopy, X-ray photoelectron spectroscopy, X-ray absorption fine structure analysis, and N2 sorption techniques revealed intercalated CoO nanoparticles inside a carbon matrix with uniform mesopore sizes (～3 nm), high surface area (～504 m2/g), and large pore volumes (～0.38 cm3/g). Additionally, very small Pd clusters consisting of approximately three atoms and Pd-O bonds formed on the interface between CoO and Pd nanoparticles. The unsaturated coordinative Pd may be responsible for the activation of chlorobenzene in the absence of any additives or ligands. Uniform mesopores and the hydrophobic nature of the carbon support may also facilitate the mass transfer of the reactant molecules and enrichment inside pores. For comparison, the catalytic activities of Pd catalysts supported on pristine mesoporous carbon and carbon embedded with nickel oxide nanoparticles were also tested.
Suzuki-Miyaura coupling in the presence of (2,2,2-triferrocenylethyl)diphenylphosphane
Garabatos-Perera, Jose Ramon,Butensch?n, Holger
, p. 357 - 360 (2008)
The electron rich and sterically bulky title phosphane was prepared and efficiently applied in the palladium catalyzed Suzuki-Miyaura cross-coupling reaction. With electron rich aryl chlorides and bromides the yields and reaction times were significantly improved by microwave heating.
Di- and Tetranuclear Palladium(II) Complexes Containing C,N-Bidentate Furoylhydrazone for Suzuki–Miyaura Reactions
Qian, Hengyu,Zhang, Tongyan,Song, Liping,Yu, Shuyan,Yuan, Qi,Sun, Luyan,Zhang, Dengfeng,Yin, Zhigang,Dai, Yongxia
, p. 1337 - 1342 (2017)
Furoylhydrazones of general formula 4-R–C6H4–CH=NNH–CO–2-C4H3O [R = H (HL1) and OCH3 (HL2)] have been conveniently prepared from furan-2-carbohydrazide. The reaction of HL1 with Li2[PdClsu
Silk?Fibroin-Supported Palladium Catalyst for Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides
Albano, Gianluigi,Farinola, Gianluca M.,Giannini, Cinzia,Musio, Roberta,Omenetto, Fiorenzo G.,Rizzo, Giorgio,Sibillano, Teresa
, (2022/02/03)
Recently, we have reported the preparation of a silk fibroin-supported Palladium catalyst (Pd/SF) and its use in the Suzuki-Miyaura cross-coupling of aryl iodides. Since its synthetic applicability and structural features are still far from being fully ex
'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction
Ding, Chengrong,Guan, Chenfei,Miao, Huihui,Zhang, Guofu,Zhao, Yiyong
supporting information, p. 3560 - 3564 (2022/03/07)
An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is
