825-55-8Relevant articles and documents
Seven-membered Pd(II) complexes containing symmetric phosphorus ylides: Synthesis, characterization and high catalytic activity toward Suzuki cross-coupling reactions
Sabounchei, Seyyed Javad,Panahimehr, Mohammad,Ahmadi, Mohsen,Akhlaghi, Fateme,Boscovic, Collete
, p. 81 - 90 (2014)
The reaction of 1,2-bis(diphenylphosphino)ethane (dppe) with various ketones in acetone produces the new phosphonium salts [RC(O)CH 2PPh2(CH2)2PPh2CH 2C(O)R]X2 (R = 2-naphtyl, X
Preparation of Co-Pd bimetallic nanoparticles encapsulated in bamboo-like N-doped mesoporous carbon by a facile one-pot method for green Suzuki coupling
Wu, Li,Long, Yu,Ma, Jiantai,Lu, Gongxuan
, p. 3809 - 3821 (2019)
CoPd bimetallic nanoparticles (NPs) were successfully encapsulated in bamboo-like N-doped mesoporous carbon (bNMC) via a facile one-pot method through combination of dissolving chelation and carbonization reactions. The morphology, structure and composition of CoPd-bNMC was verified by detailed characterization including SEM, TEM, EDX, XPS, XRD, N2 adsorption–desorption, VSM, and ICP. The as-prepared CoPd/bNMC showed excellent activity and selectivity for Suzuki coupling under mild and green condition. Though the Pd content of CoPd/bNMC was half of Pd/bNMC, the catalytic performance of CoPd/bNMC was almost the same with Pd/bNMC, which was caused by its special bimetallic alloy structure, high BET surface area and pore volume. Importantly, CoPd/bNMC with magnetic property can be separated using external magnetic field and reused for five consecutive runs in the reaction of Suzuki crossing without significant loss of activity. It was found the Pd content only showed slight loss (2.3?wt.%) after five reused reactions, which was because CoPd bimetallic NPs were inside the bamboo-like N-doped mesoporous carbon.
Easy conversion of nitrogen-rich silk cocoon biomass to magnetic nitrogen-doped carbon nanomaterial for supporting of Palladium and its application
Akbarzadeh, Parisa,Koukabi, Nadiya
, (2021)
In this study, magnetic nitrogen-doped carbon (MNC) was fabricated through facile carbonization and activation of natural silk cocoons containing nitrogen and then combined with Fe3O4 nanoparticles to create a good support material for palladium. Palladium immobilization on the support resulted in the formation of magnetic nitrogen-doped carbon-Pd (MNC-Pd). The prepared heterogeneous catalyst was well characterized using FT-IR, TGA, EDX, FE-SEM, XRD, VSM, and ICP-OES techniques. Thereafter, the synthesis of biaryl compounds was conducted to investigate the catalyst performance via the reaction of aryl halides and phenylboronic acid. Further, the catalyst could be used and recycled for six consecutive runs without any significant loss in its activity.
Recyclable and ligandless suzuki coupling catalyzed by carbon nanotube-supported palladium nanoparticles synthesized in supercritical fluid
Pan, Horng-Bin,Yen, Clive H.,Yoon, Byunghoon,Sato, Masaki,Wai, Chien M.
, p. 3473 - 3478 (2006)
Carbon nanotube-supported palladium nanoparticles prepared by a supercritical fluid deposition method show high activities for catalyzing Suzuki coupling reactions, and the catalysts can be recycled and reused at least six times without losing activity. Copyright Taylor & Francis Group, LLC.
Synthesis, transition metal chemistry and catalytic reactions of ferrocenylbis(phosphonite), [Fe{C5H4P(OC6H 3(OMe-o)(C3H5-p))2}2]
Rao, Sowmya,Mague, Joel T.,Balakrishna, Maravanji S.
, p. 11695 - 11708 (2013)
The new metalloligand ferrocenylbis(phosphonite), [Fe(C5H 4PR2)2 (R = OC6H3(OMe-o) (C3H5-p))], (2), is synthesized by the reaction of bis(dichlorophosphino)ferrocene Fe(C5H4PCl 2)2 (1) with 4-allyl-2-methoxyphenol. The reactions of 2 with H2O2 and elemental sulfur or selenium afforded bischalcogenides, [Fe{C5H4P(E)(OC6H 3(OMe-o)(C3H5-p))2}2] (3, E = O; 4, E = S; 5, E = Se), in good yield. The bis(phosphonite) reacts with group 6 metal carbonyls and group 10 metal dichloride precursors to produce the chelate complexes [{M(CO)4}Fe{C5H4P(OC 6H3(OMe-o)(C3H5-p)) 2}2}] (6, M = Mo; 7, M = W) and [(MCl2) Fe{C5H4P(OC6H3(OMe-o)(C 3H5-p))2}2] (8, M = Pd; 9, M = Pt). The palladium(ii) complex [(PdCl2)Fe{C5H 4P(OC6H3(OMe-o)(C3H 5-p))2}2] (8) is an efficient catalyst for the Suzuki-Miyaura cross-coupling reactions (TON up to 1.5 × 105). The reaction of 2 with one equivalent of [RuCl2(η6-p- cymene)]2 yielded the binuclear complex [{Ru2Cl 4(η6-p-cymene)2}Fe{C5H 4P(OC6H3(OMe-o)(C3H 5-p))2}2] (12) in good yield. Treatment of 2 with copper chloride in a 1:1 or 1:2 molar ratio resulted in the formation of a binuclear complex, [{(CuCl)Fe{C5H4P(OC6H 3(OMe-o)(C3H5-p))2} 2}2] (13), whereas a similar reaction of 2 with CuBr and CuI in a 1:2 or 1:2.5 molar ratio yielded the novel butterfly-like deca-nuclear complexes [Cu5(μ-X)5{Fe{C5H 4P(OC6H3(OMe-o)(C3H 5-p))2}2}2]2 (14, X = Br; 15, X = I). The reaction of 2 with two equivalents of [AuCl(SMe2)] afforded the digold complex [(AuCl)2Fe{C5H 4P(OC6H3(OMe-o)(C3H 5-p))2}2] (16), with the ligand exhibiting bridged-bidentate mode of coordination. Additionally, some complexes were studied by cyclic voltammetry. The crystal structures of complexes 8, 9, 12, 15 and 16 were determined using X-ray diffraction studies.
Synthesis of Substituted Thiophenes through Dehydration and Heterocyclization of Alkynols
Chen, Lu,Chen, Zebin,Huang, Yubing,Ji, Xiaoliang,Li, Jiaming,Li, Jian,Li, Yibiao,Liu, Qiang,Liu, Yang
supporting information, p. 3555 - 3566 (2022/03/14)
A protocol was described for obtaining a variety of substituted thiophenes with functional potential via metal-free dehydration and sulfur cyclization of alkynols with elemental sulfur (S8) or EtOCS2K in moderate-to-good yields. The method provides the base-free generation of a trisulfur radical anion (S3?-) and its addition to alkynes as an initiator. This research broadens the applications of S3?-in the synthesis of sulfur-containing heterocycles.
Synthesis and characterization of palladium nanoparticles immobilized on graphene oxide functionalized with triethylenetetramine or 2,6-diaminopyridine and application for the Suzuki cross-coupling reaction
Mirza-Aghayan, Maryam,Mohammadi, Marzieh,Boukherroub, Rabah
, (2021/11/22)
Graphene oxide (GO) was functionalized with two organic ligands, triethylenetetramine (TETA) or 2,6-diaminopyridine (DAP), followed by palladium nanoparticles (Pd NPs) for the synthesis of Pd NPs/GO-TETA and Pd NPs/GO-DAP nanocomposites, respectively. The two heterogeneous nanocomposites were fully characterized and their efficiency was investigated for C[sbnd]C bond formation for the synthesis of biaryl compounds via the Suzuki cross-coupling reaction of aryl halides with arylboronic acid derivatives. The obtained results indicated that the Pd NPs/GO-TETA nanocomposite was more effective in the Suzuki coupling reaction as compared to Pd NPs/GO-DAP. Thus, the Suzuki cross-coupling reaction of different aryl halides with arylboronic acid derivatives using Pd NPs/GO-TETA nanocomposite catalyst in the presence of Na2CO3 as base in DMF/H2O (1/1) as solvent at 90 °C was carried out to afford the desired biaryl compounds in high to excellent yields (81–100%) and short reaction times (10–90 min). Additionally, Pd NPs/GO-TETA nanocomposite can be recovered and reused for 8 consecutive runs without any apparent loss of its catalytic activity, proving its high stability and potential use in organic transformations.
Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions
Kundu, Abhishek,Dey, Dhananjay,Pal, Subhankar,Adhikari, Debashis
, p. 15665 - 15673 (2021/11/16)
Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
Lipids as versatile solvents for chemical synthesis
Bayer, Annette,Gevorgyan, Ashot,Hopmann, Kathrin H.
supporting information, p. 7219 - 7227 (2021/09/28)
Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis. Suzuki-Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings proceed with quantitative yields in a range of vegetable oils, fish oil, butter and waxes used as solvents. Appropriate methodologies for high-throughput screening and sustainable isolation techniques applicable for vegetable oils and related lipids are presented.
