643-58-3Relevant articles and documents
Instantaneous carbon-carbon bond formation using a microchannel reactor with a catalytic membrane
Uozumi, Yasuhiro,Yamada, Yoichi M. A.,Beppu, Tomohiko,Fukuyama, Naoshi,Ueno, Masaharu,Kitamori, Takehiko
, p. 15994 - 15995 (2006)
Instantaneous catalytic carbon-carbon bond forming reactions were achieved in a microchannel reactor having a polymeric palladium complex membrane. The catalytic membrane was constructed inside the microchannel via self-assembling complexation at the interface between the organic and aqueous phases flowing laminarly, where non-cross-linked polymer-bound phosphine and ammonium tetrachloropalladate dissolved, respectively. A palladium-catalyzed coupling reaction of aryl halides and arylboronic acids was performed using the microchannel reactor to give quantitative yields of biaryls within 4 s of retention time in the defined channel region. Copyright
Suzuki reactions in water catalyzed by an active and reusable PMO-type Pd(II) organometal catalyst with cage-like mesoporous structure
Zhu, Fengxia,Li, Hexing
, p. 2151 - 2157 (2012)
A novel Pd(II) organometal catalyst with three-dimensional (3D) cage-like Ia3d cubic mesoporous structure and high surface area was prepared. In comparison with the corresponding catalyst with two-dimensional (2D) P6mm hexagonal mesoporous structure, the as-prepared catalyst exhibited higher activities in the water-medium Suzuki coupling reactions owing to the diminished diffusion limit. It showed comparable efficiencies with the Pd(PPh 3)2Cl2 homogeneous catalyst and could be easily recycled and reused for five times without significant loss of activity.
Efficient visible-light-driven Suzuki coupling reaction over Co-doped BiOCl/Ce-doped Bi2O2CO3composites
Zhao, Dan-Xia,Lu, Guo-Ping,Cai, Chun
, p. 1823 - 1833 (2021)
Suzuki coupling reaction is a widely practiced protocol in organic synthesis for the formation of C-C bonds. The conventional process for this reaction usually involves high temperatures and noble metals. Hence, the development of a green, cost-effective photocatalytic system is an attractive and challenging strategy for the reaction. Here, we report a modified palladium-free Co-doped BiOCl/Ce-doped Bi2O2CO3(CBCB) composite, which shows high photocatalytic activity under white LED irradiation. At room temperature, an excellent yield (91%) of the desired cross-coupling product biphenyl was obtained in environmentally friendly solvents. Density functional calculations, together with the experimental results, show that the presence of Co and Ce ions results in the appearance of some impurity levels near the Fermi level of pure BiOCl and Bi2O2CO3, which decreases their forbidden bandwidth, thus ensuring higher light absorption and superior electronic conductivity. Moreover, the intimate interfacial contact between Co-doped BiOCl and Ce-doped Bi2O2CO3planes has a significant impact on the separation and transfer of photoinduced charge carriers, which ultimately leads to a remarkable increase in visible-light-driven photocatalytic activity.
Recyclable Pd(0)-Pd(II) composites formed from Pd(II) dimers with NHC ligands under Suzuki-Miyaura conditions
Górna, Marta,Szulmanowicz, Micha? S.,Gniewek, Andrzej,Tylus, W?odzimierz,Trzeciak, Anna M.
, p. 92 - 99 (2015)
Dimeric complexes of the type [Pd(μ-X)X(NHC)]2 were employed in the Suzuki-Miyaura cross-coupling leading to 2-methylbiphenyl. The excellent activity of the studied dimers is perfectly illustrated by a TOF of up to 106 h-1. Mechanistic investigations with the application of TEM, XPS, and mercury poisoning tests provided an insight into the nature of the catalytic process. Accordingly, the reduction of the dimeric palladium complex [Pd(μ-X)X(NHC)]2 resulted in the formation of a composite containing Pd(0) nanoparticles protected by a layer of a Pd(II) species such as anions [PdBr4]2- or [PdBr3(NHC)]-. The in situ formation of Pd(0)-Pd(II) composites resulted in the high stability of the catalytic system, which was active in ten subsequent recycles without any additional protection.
Orthometallated palladium trimers in C-C coupling reactions
B?aszczyk, Izabela,Gniewek, Andrzej,Trzeciak, Anna M.
, p. 44 - 52 (2012)
A series of trimeric palladium complexes of the [Pd3(μ-Cl) 4(P-C)2] (P-C = orthometallated aryl phosphite) formula have been prepared and structurally characterized using 31P NMR and ESI-MS methods. The structure of [Pd3(μ2-Cl) 4{k2-P,C-P(O-o-CH3C6H 3)(O-o-CH3C6H4)2} 2], 1c, was determined by X-ray diffraction. It is compared with the structure of the dimeric complex [Pd2(μ-Cl)2{k 2-P,C-P(O-m-CH3C6H3)(O-m-CH 3C6H4)2}2], 3b. The trimeric palladium complexes very efficiently catalyzed the Suzuki-Miyaura and Hiyama reactions in ethane-1,2-diol and the Sonogashira cross-coupling in ionic liquids. The mercury test confirmed the homogeneous pathway of the Suzuki-Miyaura reaction, although Pd(0) nanoparticles were observed by TEM in the post-reaction mixture.
A palladium Chugaev carbene complex as a modular, air-stable catalyst for Suzuki-Miyaura cross-coupling reactions
Moncada, Adriana I.,Khan, Masood A.,Slaughter, LeGrande M.
, p. 1399 - 1403 (2005)
A new Chugaev-type palladium carbene complex was prepared via a convenient metal-templated route and fully characterized by X-ray crystallography, NMR, and IR. This complex proved effective as a precatalyst for Suzuki-Miyaura cross-coupling reactions of a range of aryl bromides, even under aerobic conditions, and its modular synthesis should allow for further catalyst fine-tuning.
Suzuki-Miyaura Cross-Coupling Reaction with Potassium Aryltrifluoroborate in Pure Water Using Recyclable Nanoparticle Catalyst
Kawase, Misa,Matsuoka, Kyosuke,Shinagawa, Tsutomu,Hamasaka, Go,Uozumi, Yasuhiro,Shimomura, Osamu,Ohtaka, Atsushi
, p. 57 - 61 (2021/11/13)
This paper describes the Suzuki Miyaura cross-coupling reaction of aryl bromides with potassium aryltrifluoroborates in water catalyzed by linear polystyrene-stabilized PdO nanoparticles (PSPdONPs). The reaction of aryl bromides having electron-withdrawing groups or electron-donating groups took place smoothly to give the corresponding coupling product in high yields. The catalyst recycles five times without significant loss of catalytic activity although a little bit increase in size of PdNPs was observed after the reaction.
Nickel(II) complexes with N,O-donor thiopseudourea ligands: Syntheses, structures, and catalytic applications in Kumada–Corriu cross-coupling reactions
Shakunthala, Kinche,Srivastava, Ankit Kumar,Babu, G. Narendra,Keesara, Srinivas,Pal, Samudranil
, (2021/04/19)
Synthesis, characterization, and physical properties of benzyl-N′-(4-R-benzoyl)-N-(2,6-diisopropylphenyl)carbamimidothioates, HL1 (R = H) and HL2 (R = Cl), and their nickel(II) complexes having the general molecular formula [Ni(L1/2)2] (1 and 2) have been reported. Elemental analysis, magnetic susceptibility, solution electrical conductivity, and various spectroscopic (IR, UV–Vis, and 1H NMR) measurements were used to characterize HL1, HL2, and the two complexes (1 and 2). The molecular structures of all four compounds were determined by single-crystal X-ray crystallographic studies. The structures of HL1 and HL2 showed the imino-ketone form of both compounds. In each of 1 and 2, the six-membered chelate ring forming iminolate-O and azomethine-N donor two (L1/2)? ligands form a square-planar trans-N2O2 coordination environment around the metal center. The spectroscopic characteristics of HL1, HL2, 1, and 2 are consistent with their molecular structures. Both complexes were successfully employed as efficient catalysts in Kumada–Corriu C-C cross-coupling reactions of aryl bromides with phenylmagnesium bromide. The reactions provided biaryl products in good to excellent yields with a good substrate scope.
Fe3O4-SAHPG-Pd0 nanoparticles: A ligand-free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and C-H activation of pyrimidine cores
Azizollahi, Hamid,Eshghi, Hossein,García-López, José-Antonio
, (2020/09/17)
This paper reports a green magnetic quasiheterogeneous efficient palladium catalyst in which Pd0 nanoparticles have been immobilized in self-assembled hyperbranched polyglycidole (SAHPG)-coated magnetic Fe3O4 nanoparticles (Fe3O4-SAHPG-Pd0). This catalyst has been used for effective ligandless Pd catalyzed Suzuki–Miyaura coupling reactions of different aryl halides with substituted boronic acids at room temperature and in aqueous media. Herein, SAHPG is used as support; it also acts as a reducing agent and stabilizer to promote the transformation of PdII to Pd0 nanoparticles. Also, this environmental friendly quasiheterogeneous catalyst is employed for the first time in the synthesis of new pyrimido[4,5-b]indoles via oxidative addition/C-H activation reactions on the pyrimidine rings, which were obtained with higher yield and faster than when Pd(OAc)2 was used as the catalyst. Interestingly, the above-mentioned catalyst could be recovered in a facile manner from the reaction mixture by applying an external magnet device and recycled several times with no significant decrease in the catalytic activity.
