6301-56-0Relevant academic research and scientific papers
Palladium phosphine complex catalysts immobilized on silica via a tripodal linker unit for the Suzuki-Miyaura coupling reactions of aryl chlorides
Fukaya, Norihisa,Onozawa, Syun-Ya,Ueda, Masae,Miyaji, Takayuki,Takagi, Yukio,Sakakura, Toshiyasu,Yasuda, Hiroyuki
, p. 7 - 12 (2014)
Silica-immobilized palladium phosphine complex catalysts bearing a tripodal linker unit were tested for their ability to facilitate the Suzuki-Miyaura coupling reactions of aryl chlorides. The catalyst containing the tripodal linker with a trimethylsilyl capping group on the residual surface silanol groups displayed better catalytic activities and lower palladium and phosphorus leaching levels than the catalysts bearing a conventional trialkoxy-type linker.
Synthesis of alkyl biphenyl-4-carboxylates by reaction of biphenyl with carbon tetrachloride and alcohols in the presence of Fe2(CO)9
Bayguzina,Erokhina,Khusnutdinov
, (2017)
Alkyl biphenyl-4-carboxylates have been synthesized with high selectivity by multicomponent reaction of biphenyl with carbon tetrachloride and aliphatic alcohols in the presence of iron-containing catalysts.
Synthesis of Pd/SiO2 nanobeads for use in suzuki coupling reactions by reverse micelle sol-gel process
Kim, Mijong,Heo, Eunjung,Kim, Aram,Park, Ji Chan,Song, Hyunjoon,Park, Kang Hyun
, p. 588 - 593 (2012)
Pd/SiO2 nanobeads containing tiny Pd clusters with a diameter of about 2 nm were prepared via a sol-gel process for SiO2 by using a water-in-oil microemulsion with Pd complexes and subsequent hydrogen reduction by heat treatment. The Pd/SiO2 nanostructures were employed in Suzuki coupling reactions with various substrates, and they served as good catalysts in these reactions.
PEG modification effect of silica on the Suzuki-Miyaura coupling reaction using silica-immobilized palladium catalysts
Onozawa, Shun-Ya,Fukaya, Norihisa,Saitou, Kaori,Sakakura, Toshiyasu,Yasuda, Hiroyuki
, p. 866 - 871 (2011)
The Pd phosphine complex catalysts immobilized onto polyethylene glycol (PEG)-modified silica were prepared in order to clarify the effect of the PEG modification on the Suzuki-Miyaura coupling reaction in organic solvents. For the reaction of ethyl p-bro
Heterogeneous High-Loading Hyperbranched Polyglycidol with Peripheral NHC–Pd Complex: Synthesis and Application as Catalyst in Suzuki Coupling Reaction
Anjali,Sreekumar
, p. 1952 - 1964 (2019)
Abstract: A new polymer-supported highly functionalized dendritic polyether with peripheral NHC–Pd complex was developed by the simple anionic ring opening polymerization of glycidol on bis(3-hydroxypropyl) amine grafted Merrifield resin and its subsequent functional modification of hydroxyl group to NHC–Pd complex. The polymeric material had high stability and swelling capacity in a wide range of solvents, even in water. Similar to supported higher generation dendrimer, the newly developed system showed high palladium content with uniformly distributed and well isolated metal nanocentres. The palladium content was found to be 2.02?mmol/g which was comparatively higher than other heterogeneous NHC–Pd based catalysts and the polymer was used as heterogeneous palladium catalyst for Suzuki coupling reaction. Various factors affecting the catalyst’s performance were studied. The high availability and increased accessibility of catalytic sites, stability and dendrimer like property of the polymeric support, reusability, better resistance to metal leaching, easy synthesis etc. are the important features of this newly synthesized catalytic system. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron
Qiu, Di,Li, Songyi,Yue, Guanglu,Mao, Jinshan,Xu, Bei,Yuan, Xinyu,Ye, Fei
, (2021/11/04)
The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.
[Pd(4-R3Si-IPr)(allyl)Cl]/K2CO3/EtOH: A highly effective catalytic system for the Suzuki-Miyaura cross-coupling reaction
Choe, Yoong-Kee,Choi, Jun-Chul,Faried, Miftah,Fukaya, Norihisa,Lee, Vladimir Ya.,Matsumoto, Kazuhiro,Mizusaki, Tomoteru,Putro, Wahyu S.,Seo, Yuto,Takagi, Yukio
, (2021/10/05)
A series of R3Si-NHC-Pd complexes 1Pd-7Pd was successfully tested as a pre-catalyst for the Suzuki-Miyaura cross-coupling reaction of aryl chlorides and arylboronic acid derivatives to form a wide range of valuable biphenyl products. Use of the readily available weakly basic potassium carbonate as a base and the highly polar protic ethanol as the reaction solvent gave the target coupling products in good-to-excellent yields. The experimental data pointed to the crucial importance of the preliminary pre-catalyst activation step [i.e., the conversion of Pd(II) to Pd(0)], which is remarkably facilitated by the electron-donating trialkylsilyl groups on the NHC ligands of 1Pd–7Pd, thereby rendering them superior compared to the commercially available IPr-Pd complexes. Computational analysis revealed the mechanism of the Pd(II)→Pd(0) activation step, demonstrating the critical role of the reaction solvent and the base in the preference of our 1Pd–7Pd pre-catalysts, for which this step is both thermodynamically and kinetically more feasible.
Aminomethylpyridinequinones as new ligands for PEPPSI-type complexes
Gajda, Roman,Poater, Albert,Brotons-Rufes, Artur,Planer, Sebastian,Wo?niak, Krzysztof,Grela, Karol,Kajetanowicz, Anna
, p. 138 - 156 (2021/03/22)
A set of six new catalysts possessing quinone moieties in a pyridine ligand was synthesized and fully characterized by standard analytical techniques, including X-Ray crystallography. The results obtained in Suzuki and Mizoroki–Heck cross-coupling reactions catalyzed by quinone-based compounds were comparable to these obtained in the presence of the original PEPPSI complex designed by Organ. DFT calculations allow to see the structural and electronic factors to describe their similarity. On the other hand, steric maps and NCI plots were the tools to have a more global view of the systems studied, leaving the sphere of reactivity around the metal.
Charge Neutral [Cu2L2] and [Pd2L2] Metallocycles: Self-Assembly, Aggregation, and Catalysis
Ko?odziejski, Micha?,Brock, Aidan J.,Kurpik, Gracjan,Walczak, Anna,Li, Feng,Clegg, Jack K.,Stefankiewicz, Artur R.
supporting information, p. 9673 - 9679 (2021/06/30)
A range of morphologically distinct metallosupramolecular Cu(II) and Pd(II) complexes has been constructed, based on the tritopic ligand 1,1′,1″-(benzene-1,3,5-triyl)tris(4,4-dimethylpentane-1,3-dione) (H3L). By control of the reaction conditions, it is possible to generate distinct coordination assemblies possessing either macrocyclic or polymeric structures and more importantly distinct activity in catalysis of the Suzuki-Miyaura cross-coupling.
Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone
Valentini, Federica,Ferlin, Francesco,Lilli, Simone,Marrocchi, Assunta,Ping, Liu,Gu, Yanlong,Vaccaro, Luigi
supporting information, p. 5887 - 5895 (2021/08/23)
Herein we report a simple protocol for the valorisation of a common urban biowaste. The lignocellulosic biomass obtained after the pre-treatment of pine needle urban waste is efficiently transformed into a low-cost support (PiNe) for the immobilization of Pd nanoparticles. The final Pd/PiNe heterogeneous catalyst features a small particle size (4.5 nm) and a metal loading (9.9 wt%) comparable with most commercially available and generally used counterparts. In this contribution, we tested the catalytic efficiency of the Pd/PiNe system in two representative cross-couplings, Heck and Hiyama reactions, and compared the results obtained with commercial Pd/C catalyst. The good reactivity in the biomass-derived solvent (GVL) confirms that the Pd/PiNe heterogeneous catalyst is a valid system that can be integrated into a waste valorization chain within a circular economy approach. In addition, the efficiency of the catalyst has also been extended to perform the challenging consecutive Hiyama-Heck reaction to afford differently substituted (E)-1,2-diarylethenes.
