605-02-7Relevant articles and documents
Palladium-catalyzed coupling of aryl halides with arylhalosilanes in air and water
Huang, Taisheng,Li, Chao-Jun
, p. 403 - 405 (2002)
In the presence of a palladium catalyst, various aryl halides reacted with arylhalosilanes in aqueous media and under an air atmosphere to give the corresponding unsymmetrical aryl-aryl coupling products conveniently.
One-pot Solvent-free Catalytic Dimerization Reaction of Phenylacetylene to 1-Phenylnaphthalene
Taherpour, Avat,Taban, Sepehr,Yari, Ako
, p. 1523 - 1530 (2015)
In this study, we report a smooth one-pot, solvent-free catalytic dimerization of phenylacetylene (1) to 1-phenylnaphthalene (2) by Cu/C at room temperature in good yield (～100%). In the computational study, the structure of the 1-phenylnaphthalene was optimized by DFT-B3LYP/6-31Gmethod. The rotation barrier around C-C of the phenyl and naphthalene parts of the molecule and its UV-Visible spectrum were calculated. The modelling of the mechanism of production of 2 from 1 was performed with and without Cu/C catalyst. The data of EDS and SEM of the Cu/C catalyst surface are also reported.
Solid-supported palladium nano and microparticles: An efficient heterogeneous catalyst for ligand-free Suzuki-Miyaura cross coupling reaction
Das, Pralay,Sharma, Dharminder,Shil, Arun K.,Kumari, Avnesh
, p. 1176 - 1178 (2011)
Solid-supported nano and microparticles of Pd(0) (SS-Pd) were prepared and used as a heterogeneous catalysts for Suzuki-Miyaura cross coupling reactions of aryl halides (chloro, bromo and iodo) and phenyl boronic acid under mild and ligand-free conditions. Scanning electron microscope (SEM) and UV-vis based studies were performed to observe the distribution of nano and microparticles of palladium over solid surface and their oxidation states. In addition, the catalyst could be reused up to seven runs without significant loss of activity and stable enough under moist conditions.
Deposited zirconocene chloride on silica-layered CuFe2O4 as a highly efficient and reusable magnetically nanocatalyst for one-pot Suzuki-Miyaura coupling reaction
Zeynizadeh, Behzad,Sepehraddin, Farhad
, p. 70 - 77 (2018)
The novel core-shell magnetically nanoparticles of CuFe2O4@SiO2@ZrCp2Clx (x: 0–2) were synthesized and used as a highly efficient catalyst for Suzuki-Miyaura coupling reaction of various aryl halides with phenylboronic acid. The reactions were carried out in PEG-400 (70 °C) to afford biaryls in high to excellent yields. The core-shell nanocomposite was easily separated from the reaction by an external magnet and reused for 5 times without significant loss of its catalytic activity. Characterization of the zirconocene nanocomposite was carried out by FT-IR, SEM, EDX, XRD, ICP-OES, AGFM, TGA and BET analyses.
Combination of polymer and halloysite chemistry for development of a novel catalytic hybrid system
Sadjadi, Samahe,Malmir, Masoumeh,Pourmohammad, Nargess,Ahmadi, Shervin,Heravi, Majid M.
, p. 4349 - 4366 (2019)
Abstract: A covalent hybrid of halloysite-poly(methyl methacrylate-co-maleic anhydride) was prepared and applied for the immobilization of Pd nanoparticles. The hybrid system, Pd@Hal-Gua-Poly, was then characterized via TEM, TGA, ICP, BET, FTIR and XRD and successfully used as a heterogeneous catalyst for promoting two main Pd-catalyzed reactions, i.e. hydrogenation of nitro-arenes and Suzuki coupling reaction under mild and eco-friendly conditions. The study of recyclability of the catalyst confirmed high recyclability and low Pd leaching of Pd@Hal-Gua-Poly. Moreover, the hot-filtration test showed the heterogeneous nature of the catalysts. Notably, the comparison of the activity of the catalyst with that of Pd@Hal and Pd@Poly confirmed the superior catalytic activity of the former, indicating that the hybridization of Hal and Poly could lead to the improvement of the catalytic activity. Graphical abstract: [Figure not available: see fulltext.].
Stereo- and Regio-specific Photochemical Cycloaddition of Furan to Benzonitrile and Phenylacetylene
Gilbert, Andrew,Rodwell, Paul
, p. 1057 - 1058 (1985)
Benzonitrile and phenylacetylene undergo exclusive regio- and stereo-specific 2,6-, 2',5'-photocycloaddition of furan: excited state interaction between the substituent and furan is considered to orient the addends and direct the reaction of this specific mode of attack.
Silver(I), mercury(II) and palladium(II) complexes of functionalized N-heterocyclic carbenes: Synthesis, structural studies and catalytic activity
Liu, Qing-Xiang,Li, Hui-Long,Zhao, Xiao-Jun,Ge, Shu-Sheng,Shi, Meng-Chao,Shen, Gang,Zang, Yan,Wang, Xiu-Guang
, p. 437 - 445 (2011)
A series of NHC silver(I), mercury(II) and palladium(II) complexes, [(1,3-diethylbimy)6Ag4I3]I (2), [(1-benzyl-3-picolylbimy)Ag2Br2]n (3), [(1-benzyl-3-picolylbimy)HgI(CH2CN)]2 (4), {[(1-picolyl-3-npropylbimy)2Hg][Hg2I6]} n (5) and [(1,3-dipicolylbimy)PdCl]Cl (6), as well as one anionic complex [1,3-diethylbimidazolium]2[HgI4] (1) (bimy = benzimidazol-2-ylidene), have been prepared and characterized. Interestingly, a wind wheel-like Ag4I3 arrangement in 2 is formed, 1D polymeric chain containing 12-membered macrometallocycles and quadrangle Ag 2Br2 units in 3 is generated, and the α-carbon atom of deprotonated acetonitrile ([CH2CN]-) in 4 participates in coordination with mercury(II) atom. In the crystal packings of complexes 1-6, 2D supramolecular layers or 3D supramolecular architectures are formed via intermolecular weak interactions, including π-π interactions, hydrogen bonds, C-H?π contacts, weak Hg?I bonds and I?I bonds. Additionally, the catalytic activity of the NHC palladium(II) complex 6 in Suzuki-Miyaura cross-coupling reaction was studied.
Electrostatic Grafting of a Palladium N-Heterocyclic Carbene Catalyst on a Periodic Mesoporous Organosilica and its Application in the Suzuki-Miyaura Reaction
Rajabi, Fatemeh,Schaffner, Dirk,Follmann, Sascha,Wilhelm, Christian,Ernst, Stefan,Thiel, Werner R.
, p. 3513 - 3518 (2015)
A periodic mesoporous organosilica material functionalized with a Pd N-heterocyclic carbene complex was synthesized by applying an electrostatic grafting method. The resulting hybrid material was characterized by solid-state 29Si and 13C cross-polarization magic-angle spinning NMR spectroscopy, XRD, thermogravimetric analysis, and BET measurements. The hybrid was applied as a catalyst for the Suzuki-Miyaura cross-coupling between aryl chlorides and phenylboronic acid under heterogeneous and aerobic conditions. The supported catalyst exhibited excellent activity and stability and it could be reused at least six times without any loss of activity. Atomic absorption spectroscopy detected no Pd contamination in the products, and leaching tests verified that the reaction was truly heterogeneous. Palladium plus pores: Ionic interactions allow a palladium N-heterocyclic carbene (NHC) complex to be anchored on the surface of a sulfonated periodic mesoporous organosilica material. The resulting heterogeneous Pd-NHC catalyst is highly active in the Suzuki-Miyaura coupling of aryl chlorides under mild and aerobic conditions.
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.
Ring Contraction of Tropylium Ions into Benzenoid Derivatives
Crocker, Reece D.,Dinh, An H.,Lyons, Demelza J. M.,Mai, Binh Khanh,Nguyen, Thanh Vinh,Ton, Nhan N. H.
supporting information, p. 2520 - 2525 (2022/04/12)
We report a method to convert substituted tropylium ions into benzenoid derivatives.
MeOTf-catalyzed formal [4?+?2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion
Chen, Chao,Xi, Chanjuan,Zhang, Zeyu,Zou, Song
supporting information, (2021/12/30)
MeOTf-catalyzed formal [4 + 2] annulation of styrene oxides with alkynes to afford polysubstituted naphthalenes has been realized, which undergoes sequential electrophilic cyclization/ring expansion. A range of substrates were tolerated in the formation of naphthalene derivatives with high regioselectivity in satisfactory yields. The reaction could also be carried out on gram scale.
