324-74-3Relevant articles and documents
A water-soluble pyridyl-triazole ligand for aqueous phase palladium catalyzed Suzuki-Miyaura coupling
Amadio, Emanuele,Scrivanti, Alberto,Beghetto, Valentina,Bertoldini, Matteo,Alam, Md. Mahbubul,Matteoli, Ugo
, p. 21636 - 21640 (2013)
An environmentally friendly water-soluble ligand has been prepared by "clicking" 2-(azidomethyl)pyridine with but-3-ynyl sodium sulphate. In situ combination of the new ligand with [Pd(η3-C 3H5)Cl]2 (Pd:ligand =
Palladium Separation by Pd-Catalyzed Gel Formation via Alkyne Coupling
Yang, Xiaojiao,Chen, Jinfan,Hu, Liangsheng,Wei, Jianyu,Shuai, Maobin,Huang, Deshun,Yue, Guozong,Astruc, Didier,Zhao, Pengxiang
, p. 7386 - 7394 (2019)
Selective entrapment of precious metals from industrial wastes containing various metals is a most challenging branch of environmental science. Developed methods like solvent or solid-phase extraction, ion exchange, co-precipitation, membrane filtration, and adsorption rely on chelation, electrostatic attraction, or ion exchange, and these methods present limited selectivity and require post-treatment for further application. Herein, an original concept is reported involving the utilization of the superior catalytic properties of Pd selectively for efficient entrapment of Pd from other metals. Specifically, side chains of poly(vinyl alcohol) (PVA) functionalized with alkynyl groups are catalytically dimerized using Pd(II), which forms gels. The Pd(II) ions are coordinatively encapsulated into the gel networks, while the other metal ions are excluded from the networks, thus allowing the separation and immobilization of Pd. The entrapped Pd(II) is also reduced to Pd(0) nanoparticles (PdNPs) forming PdNPs@alkyne-PVA aerogels that exhibit a high catalytic activity for the Suzuki-Miyaura cross-coupling reaction. PdNPs@alkyne-PVA aerogels are further carbonized to PdNPs@C networks for the efficient electrochemical hydrogen evolution reaction. This method provides an effective way not only to selectively separate Pd but also to utilize the entrapped Pd resources for multiple catalyses without further post-treatment of the entrapped Pd source.
Palladacycle from cyclometalation of the unsubstituted cyclopentadienyl ring in ferrocene: Synthesis, characterization, theoretical studies, and application to suzuki-miyaura reaction
Qian, Hengyu,Yin, Zhigang,Zhang, Tongyan,Yan, Shihai,Wang, Quanling,Zhang, Chunxia
, p. 6241 - 6246 (2014)
The ferrocenylimines of general formula [(η5-C5H5)Fe(η5-C5H4)-CH2N=CH-C(R)=CH-C6H5] with R = H (2a) and CH3 (2b) were conveniently prepared from ferrocenylmethylamine. Reaction of 2a,b with lithium tetrachloropalladate in methanol in the presence of anhydrous sodium acetate resulted in the formation of the di-μ-chloro-bridged heteroannular cyclopalladated complexes 3a,b via the unsubstituted ferrocenyl C-H bond activation of the related ligands. Treatment of 3a,b with triphenylphosphine gave Pd{[(η5-C5H4)Fe(η5-C5H4)CH2N=CH-CH=CH-C6H5]}ClPPh3 (4a) and Pd{[(η5-C5H4)Fe(η5-C5H4)-CH2N=CH-C(CH3)=CH-C6H5]}ClPPh3 (4b), respectively. The crystal structures of 4a,b confirmed the formation of a carbon-palladium bond by using a carbon atom in the unsubstituted cyclopentadienyl ring. Additionally, theoretical studies using density functional theory calculations were carried out in order to account for the regioselectivity of cyclometalation. As for the catalysts, using 0.1% of palladacycles 4a,b in the presence of K3PO4·7H2O as base exhibited excellent yields in the Suzuki-Miyaura coupling reaction of aryl bromides with phenylboronic acid.
Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction
Andrews, Stephen P.,Stepan, Antonia F.,Tanaka, Hirohisa,Ley, Steven V.,Smith, Martin D.
, p. 647 - 654 (2005)
The utility of a series of palladium-containing perovskite catalysts in the Suzuki reaction is described; turnover numbers of up to 400,000 are reported. A detailed investigation into the mode of action of these catalysts encompassing kinetic studies, catalyst poisoning, microscopy and three-phase tests demonstrate that these heterogeneous materials are pre-catalysts that operate by a solution-phase mechanism.
Cross-coupling reactions catalyzed by P, O chelate palladium complexes at room temperature
Guo, Mengping,Jian, Fangfang,He, Ren
, p. 9017 - 9020 (2005)
A new catalytic system based on P, O chelate palladium complexes for cross-coupling reactions is described. These catalysts have all shown high activity and selectivity under mild reaction condition.
A mesoporous "shell-in-shell" structured nanocatalyst with large surface area, enhanced synergy, and improved catalytic performance for Suzuki-Miyaura coupling reaction
Liu, Baocang,Niu, Yuefang,Li, Yan,Yang, Fan,Guo, Jiamin,Wang, Qin,Jing, Peng,Zhang, Jun,Yun, Guohong
, p. 12356 - 12359 (2014)
A novel mesoporous "shell-in-shell" structured nanocatalyst (@Pd/meso-TiO2/Pd@meso-SiO2) with large surface area, enhanced synergy, and improved catalytic performance is created for catalyzing Suzuki-Miyaura coupling and 4-nitrophenol reduction reactions. This journal is
Palladium nanoparticles immobilized over Strawberry fruit extract coated Fe3O4 NPs: A magnetic reusable nanocatalyst for Suzuki-Miyaura coupling reactions
Hemmati, Saba,Yousefi, Mohammad,Salehi, Mirmehdi Hashemi,Amiri, Mahdis,Hekmati, Malak
, (2020)
This paper develops a green method for in situ decorated of palladium nanoparticles over Fe3O4 nanoparticles, by utilizing Strawberry fruit extract and ultrasound irradiations, with no use of any toxic reducing agent. The structure's characterization is represented via diverse analytical methods such as FT-IR, FE-SEM, TEM, WDX, ICP, EDS and XXPS. Catalytic efficiency of magnetic Fe3O4@Strawberry/Pd nanocatalyst is investigated in production of different biphenyls with good turnover frequencies (TOF) and turnover numbers (TON) through Suzuki coupling reactions. Furthermore, the catalyst could be recovered and reused 7 runs without considerable palladium leaching or alteration in its performance.
In situ generated and stabilized Pd nanoparticles by N2,N4,N6-tridodecyl-1,3,5-triazine-2,4,6-triamine (TDTAT) as a reactive and efficient catalyst for the Suzuki-Miyaura reaction in water
Iranpoor, Nasser,Rahimi, Sajjad,Panahi, Farhad
, p. 3084 - 3090 (2016)
In situ generated Pd nanoparticles in the presence of N2,N4,N6-tridodecyl-1,3,5-triazine-2,4,6-triamine (TDTAT) were found to be an efficient catalyst for the Suzuki-Miyaura coupling reaction in water. It seems that TDTAT not only acts as a ligand for stabilization of the produced nanoparticles, but also as a surfactant to facilate the reaction in water, and reduces Pd(ii) to Pd(0). The TEM analysis of the reaction mixture showed that Pd nanoparticles with an average size of ～5 nm are produced, which act as an efficient catalyst in the Suzuki-Miyaura coupling reaction.
Magnetic Core–Shell to Yolk–Shell Structures in Palladium-Catalyzed Suzuki–Miyaura Reactions: Heterogeneous versus Homogeneous Nature
Li, Yinle,Zhang, Zhuqing,Fan, Tao,Li, Xiaoguang,Ji, Jin,Dong, Pei,Baines, Robert,Shen, Jianfeng,Ye, Mingxin
, p. 564 - 573 (2016)
This study describes a comparative investigation on the heterogeneous versus homogeneous nature of the Pd-catalyzed Suzuki–Miyaura cross-coupling reaction mechanism with specific magnetic hierarchical core–shell and yolk–shell structures. The hierarchical core–shell Fe3O4@SiO2-Pd@mCeO2 (m=mesoporous) catalyst contains a core of nonporous silica-sheltered magnetite (Fe3O4) nanoparticles (NPs), a transition layer of active palladium (Pd) NPs, and an outer shell of porous ceria (CeO2). The magnetic yolk–shell Fe3O4@h-Pd@mCeO2 (h=hollow) catalyst was prepared by selectively etching the nonporous silica interlayers. Notably, the results of the hot-filtration heterogeneity test, the effect of Pd concentration, and solid-phase poisoning, indicate that the two kinds of catalysts function in Pd-catalyzed Suzuki–Miyaura cross-coupling reactions through different catalytic mechanisms. Moreover, both catalysts demonstrated better catalytic activity than the Fe3O4@SiO2-Pd catalyst. This finding can be ascribed to the outermost CeO2 shell having a high concentration of trivalent cerium and oxygen vacancies, which gives rise to the increased electron density of Pd NPs, and a faster rate-determining step in the oxidative addition reaction for the Suzuki reaction. In addition, we propose a feasible mechanism elucidating the synergistic effect between the supporting CeO2 and active species.
The air-stable and highly efficient P, N-chelated palladium(II) complexes as catalysts for the Suzuki cross-coupling reaction at room temperature
Guo, Mengping,Jian, Fangfang,He, Ren
, p. 2033 - 2036 (2006)
Two air-stable P, N-chelated palladium(II) complexes have been evaluated as highly efficient and simple catalysts for Suzuki cross-coupling reaction between aryl bromides and arylboronic acids. They exhibit high activity and selectivity at room temperature.
