135-70-6Relevant academic research and scientific papers
Polyamine anchored palladium catalyst for suzuki-miyaura and one-pot O-alkylation-suzuki reactions
Patel, Krupa N.,Bedekar, Ashutosh V.
, p. 1710 - 1717 (2015)
Polymer anchored amine-palladium complexes were screened as catalysts for Suzuki-Miyaura coupling reactions of aryl halides. The robust, recyclable catalyst was effective in this reaction of aryl bromides and iodides. Aryl bromide was found to undergo selective Suzuki-Miyaura reaction with phenyl boronic acid, even in presence of styrene. The catalyst system was further employed for one-pot O-alkylation-Suzuki reaction to prepare alkoxy biaryl systems in good conversions.
Porous aromatic framework with mesopores as a platform for a super-efficient heterogeneous Pd-based organometallic catalysis
Jing, Li-Ping,Sun, Jin-Shi,Sun, Fuxing,Chen, Peng,Zhu, Guangshan
, p. 3523 - 3530 (2018)
A strategy using a mesoporous amine-tagged porous aromatic framework (PAF70-NH2) to immobilize a palladium (Pd)-based molecular catalyst has been developed. The resulting immobilized catalyst PAF70-Pd, in which the framework is entirely constructed by phenyl rings linked with stable carbon-carbon bonds, has high structural rigidity and stability. Compared with the known porous organic material immobilized Pd-based catalysts, PAF70-Pd has the highest Pd content so far. Moreover, PAF70-Pd has extremely high catalytic activity with good size selectivity and very easy recyclability in catalyzing the Suzuki-Miyaura coupling reaction. In the current system, the catalyst loading could be as low as 0.001 mol% and the TOF value could go up to 28800 h-1 which is far higher than those of the known porous organic material immobilized Pd-based catalysts. In order to elucidate the particularly high catalytic efficiency of PAF70-Pd, we prepared PAF1-Pd from PAF1-NH2 for comparison. PAF1-Pd has a higher Pd content than PAF70-Pd. However, due to the absence of large enough mesopores in PAF1-NH2, PAF1-Pd has almost no catalytic activity under the same conditions, which definitely demonstrated that the intrinsic mesoporosity of PAF70-NH2 plays a crucial role in the superb catalytic efficiency of PAF70-Pd. This strategy to immobilize Pd-based molecular catalysts has very good expansibility to be applied in the immobilization of different organometallic catalysts into the pores of PAFs, which also has very high potential in the chemical and pharmaceutical industry.
Electrochemical synthesis of PdII polynuclear complexes based on biquinolyl-containing polymers and their catalytic activity in the Suzuki reaction
Magdesieva,Nikitin,Abdullin,Polyakova,Yakimanskiy,Goikhman,Podeshvo
, p. 1423 - 1430 (2009)
Electrochemical dissolution of sacrificial Pd anode was used to synthesize novel polynuclear PdII complexes with ligands based on polyamic acids containing in the main chain biquinolyl groups capable of coordination to the metal ions. The synthesized polymeric complexes exhibit high catalytic activity in the Suzuki reaction. The reaction can be run under mild conditions, at 40 °C and with a sufficiently high product yield at a catalyst concentration of 0.05 mol.% (with respect to the starting aryl halide). The polymeric ligand allows immobilization of the catalyst on the graphite fabric with high specific surface area that enhances the catalyst turnover number and promotes its recycling.
Microwave-assisted Suzuki coupling on a KF-alumina surface: Synthesis of polyaryls
Basu, Basudeb,Das, Pralay,Bhuiyan, Md. Mosharef H.,Jha, Satadru
, p. 3817 - 3820 (2003)
A range of conjugated polyaryls has been synthesized through one-pot microwave assisted palladium-catalyzed consecutive Suzuki coupling reactions on a KF-alumina surface with notable features including rapid reaction times, solvent-free conditions, high yields, atom economic and air-insensitive reactions.
Stable ferrocenyl-NHC Pd(II) complexes: Evidence of C-H ?H/π interaction and M-O bonding in solution
Azpiroz, Ramón,Sharma, Pankaj,Javier Pérez-Flores,Gutierrez, René,Espinosa-Pérez, Georgina,Lara-Ochoa, Francisco
, p. 196 - 206 (2017)
New air stable palladium(II)-NHC complexes where carbene ligand is substituted with a bulky ferrocenylmethyl and pyranylmethyl groups viz. PdI(Phpy){FcCH2-C3H2N2-Me} (3), PdI2{FcCH2-C3H2N2-C6H11O} (4) and PdI2{FcCH2-NHC}(L) (5–10) (NHC = C3H2N2-Me or C6H11O; L = pyridine, imidazole and thiazole) are reported. The presence of C-H?H/π interactions has been confirmed for complex 3 by NOE interaction and multinuclear NMR experiments. In addition, for this complex, a quantum chemical analysis was performed using PM3 semi-empirical calculations to find the possible conformers. The conformation with minimal energy confirms the NMR interpretation for complex 3. The M-O bond in complex 4 was ruptured by the reaction of an extra pyridine ligand to afford PdI2{FcCH2-C3H2N2-C6H11O}(py) (5) which was synthetized differently by reacting NHC ligand, Pd(OAc)2 and pyridine. Molecular structure of complex 5 was determined by X-ray diffraction. The catalytic activity of these complexes was checked in Suzuki-Miyaura reaction. Complex 5 exhibits excellent conversions and selectivities (up to 99%).
An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks
Adams, Kirsty,Ball, Anthony K.,Birkett, James,Brown, Lee,Chappell, Ben,Gill, Duncan M.,Lo, P.K. Tony,Patmore, Nathan J.,Rice, Craig R.,Ryan, James,Raubo, Piotr,Sweeney, Joseph B.
, p. 396 - 401 (2017)
Heterocyclic architectures offer powerful creative possibilities to a range of chemistry end-users. This is particularly true of heterocycles containing a high proportion of sp3 -carbon atoms, which confer precise spatial definition upon chemical probes, drug substances, chiral monomers and the like. Nonetheless, simple catalytic routes to new heterocyclic cores are infrequently reported, and methods making use of biomass-accessible starting materials are also rare. Here, we demonstrate a new method allowing rapid entry to spirocyclic bis-heterocycles, in which inexpensive iron(III) catalysts mediate a highly stereoselective C-C bond-forming cyclization cascade reaction using (2-halo)aryl ethers and amines constructed using feedstock chemicals readily available from plant sources. Fe(acac) 3 mediates the deiodinative cyclization of (2-halo)aryloxy furfuranyl ethers, followed by capture of the intermediate metal species by Grignard reagents, to deliver spirocycles containing two asymmetric centres. The reactions offer potential entry to key structural motifs present in bioactive natural products.
Steering Surface Reaction Dynamics with a Self-Assembly Strategy: Ullmann Coupling on Metal Surfaces
Zhou, Xiong,Wang, Chenguang,Zhang, Yajie,Cheng, Fang,He, Yang,Shen, Qian,Shang, Jian,Shao, Xiang,Ji, Wei,Chen, Wei,Xu, Guoqin,Wu, Kai
, p. 12852 - 12856 (2017)
Ullmann coupling of 4-bromobiphenyl thermally catalyzed on Ag(111), Cu(111), and Cu(100) surfaces was scrutinized by scanning tunneling microscopy as well as theoretical calculations. Detailed experimental evidence showed that initial formation of organom
N-Heterocyclic Carbene–Palladium Complex onto Graphene Oxide and Poly (ethylene glycol) (PEG) Applied as Superior Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water
Heravi, Majid M.,Asadi, Shima,Hoseini Chopani, Seyede Mahdiye,Jaderi, Elham
, (2020)
Using polymeric nanocomposites incorporated Pd to promote C-C coupling reactions has been found as one of the most successful strategies. In this paper we apply graphene oxide (GO) as an efficient surface immobilized by water-soluble poly (ethylene glycol)-imidazole followed by introduction of PdCl2 salt to obtain the desired catalyst. Catalytic performance of this composite was investigated in the Suzuki–Miyaura cross-coupling reaction under mild reaction conditions and superior results were obtained. The hydrophilic nature of the catalyst and well distribution of Pd lead to superior catalytic activity in water media. Moreover, the Suzuki–Miyaura reaction proceed successfully with excellent yield and short reaction time without any loss of activity even after seven consecutive reaction cycles.
Rapid Access to Bi- and Tri-Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions
Wern, Caroline,Ehrenreich, Christian,Joosten, Dominik,Stein, Thorsten vom,Buchholz, Herwig,K?nig, Burkhard
, p. 5644 - 5656 (2018)
Syntheses of 1,2-, 1,3-, 1,4-, 1,8-, 2,4-, 3,4-, 4,8-, 1,2,4-, 1,2,8- and 1,3,4-functionalized dibenzofurans in few steps with good to excellent yields starting from dibenzofuran-1-ol or -4-ol are presented. These rapidly accessible bi- or tri-functionalized building blocks are of great interest for the synthesis of bioactive substances or functional material development. Furthermore, for intermediates containing both a bromine and a triflate moiety, a selective mono-substitution by means of Suzuki–Miyaura reaction (SMR) is described.
Homocoupling of arylboronic acids and potassium aryltrifluoroborates catalyzed by protein-stabilized palladium nanoparticles under air in water
Prastaro, Alessandro,Ceci, Pierpaolo,Chiancone, Emilia,Boffi, Alberto,Fabrizi, Giancarlo,Cacchi, Sandro
, p. 2550 - 2552 (2010)
Palladium nanoparticles stabilized primarily within the protein cavity of a highly thermostable Dps protein (DNA binding protein from starved cells) from the thermophilic bacterium Thermosynechoccus elongatus provide an efficient catalyst for the homocoupling of boronic acids and potassium aryltrifluoroborates in water under aerobic phosphine-free conditions. Symmetrical biaryls have been isolated in good to excellent yields. Potassium aryltrifluoroborates give similar or better results than the corresponding arylboronic acids.
