1625-92-9Relevant academic research and scientific papers
Immobilized palladium nanoparticles within polymers as active catalysts for Suzuki-Miyaura reaction
Chen, Ting,Mao, Fei,Qi, Zhengliang,Li, Yan,Chen, Rizhi,Wang, Yong,Huang, Jun
, p. 16899 - 16903 (2016)
A highly active and reusable catalyst Pd@PNP was developed for Suzuki-Miyaura reaction of aryl chlorides and bromides with aryl boronic acids, and the corresponding biphenyl compounds were obtained in good to excellent yields. Triphenylphosphine and palladium nanoparticles were immobilized in situ in the polymer formed from Pd catalyzed coupling of tris(4-bromophenyl)amine and benzene-1,4-diboronic acid. The immobilized triphenylphosphine enhanced the activity and the stability of the catalyst Pd@PNP, and the catalyst Pd@PNP can be reused at least 5 times with good activity. Functional groups, such as methoxyl, nitrile, tert-butyl, nitro, acyl and formyl groups, were well tolerated under the reaction conditions, and the corresponding products were obtained in high yields.
Novel polymer incarcerated palladium with phosphinated polymers: Active catalyst for Suzuki-Miyaura coupling without external phosphines
Nishio, Ryo,Sugiura, Masaharu,Kobayashi, Shu
, p. 4831 - 4834 (2005)
(Chemical Equation Presented) Immobilization of a palladium catalyst with use of new phosphinated polymers was carried out utilizing the polymer incarcerated (PI) method. This phosphinated PI Pd catalyst showed excellent activity in Suzuki-Miyaura couplin
One-pot preparation of magnetic N-heterocyclic carbene-functionalized silica nanoparticles for the Suzuki-Miyaura coupling of aryl chlorides: Improved activity and facile catalyst recovery
Yang, Hengquan,Wang, Yunwei,Qin, Yong,Chong, Yanzhu,Yang, Qiaozhen,Li, Guang,Zhang, Li,Li, Wei
, p. 1352 - 1361 (2011)
Based on a reverse micelle strategy, we successfully synthesized new magnetic silica nanoparticles functionalized with a bulky N-heterocyclic carbene (N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, denoted as IPr) precursor through the co-condensation of IPr-bridged organosilane and tetraalkoxysilane in a one-pot reaction. TEM and SEM investigations revealed that the particle sizes of the synthesized materials were uniformly distributed in the range 15-30 nm, and could be tuned by varying the amount of siliceous precursors. FT-IR and XPS characterizations showed that the IPr ligand was successfully incorporated onto magnetic silica nanoparticles. Such materials show good coordination capability toward Pd(acac)2 (acac = acetylacetonate), leading to a higher loading in comparison with magnetic silica nanoparticles (without functionalization). This Pd-loaded material is active toward the Suzuki-Miyaura couplings of challenging aryl chlorides under relatively mild conditions (at 80°C). An 81% yield for biphenyl was achieved in the presence of 0.32 mol% of Pd within 8 h, using iso-propyl alcohol as a solvent and KOtBu as a base. The activity of the functionalized nanoparticles is much higher than that of mesoporous silica-based catalysts, as well as a commercial Pd/C catalyst. This catalyst can be easily isolated by using a magnetic field and directly used in the next reaction cycle without significant loss of its activity.
Highly active PdCu/graphene catalyst for an efficient Suzuki cross-coupling reaction
M., Xiaojing,Gao, Lingfeng,Weng, Zhentao,Yang, Hua,Sun, Xu
, p. 20525 - 20529 (2020)
A graphene supported Pd-Cu bimetallic catalyst (Pd-Cu/G) has been successfully fabricated by a simple one-pot solvothermal reaction. X-ray diffraction (XRD) analysis as well as morphology characterization demonstrated that Pd-Cu nanoparticles (NPs) are uniformly distributed on the graphene nanosheets. When adopted as the catalyst for the Suzuki cross-coupling reaction, this hybrid exhibited excellent catalytic activity (99.9% conversion) as well as desirable selectivity (99.9%). After recycling five times, the high yield and selectivity were well maintained, illustrating the high durability of this catalyst. This journal is
Polyfluorinated phosphine ligands in the room temperature Suzuki cross-coupling reactions
Yekta, Shahla,Cheung, Lawrence,Yudin, Andrei K.
, p. 8048 - 8051 (2007)
Polyfluorinated phosphine ligands can be obtained by regioselective nucleophilic aromatic substitution on tetrafluoronaphthalene derivatives. The ligand efficiency has been demonstrated in the room temperature Suzuki coupling reactions of aryl bromides an
Studies on the functionalization of MWNTs and their application as a recyclable catalyst for CC bond coupling reactions
Kim, Eunsuk,Jeong, Han Saem,Kim, B. Moon
, p. 71 - 74 (2014)
Functionalization of multi-walled carbon nanotubes (MWNTs) was studied using various anchoring methods. Among them, nitrene chemistry was employed as the method of choice to preserve desirable physical properties of MWNTs. Using this method, synthesis of carboxyl-functionalized carbon nanotubes (CNTs) was achieved, and then transition metals were incorporated on the linker-MWNT via reductive methods using hydrazine monohydrate. Among various reducing reagents, the use of hydrazine hydrate allowed us to load palladium uniformly. After immobilization of palladium on CNT, its role as a catalyst for CC bond coupling reaction (Suzuki reaction) was examined. The catalysts could be retrieved upon completion of the reaction by filtration and drying; the recycled catalysts could then be used in further reactions up to seven times before any loss in catalytic activity was observed. Further studies revealed that the Pd leached out of the MWNT may be responsible for the reactivity.
The catalytic ability of various transition metals in the direct functionalization of aromatic C-H bonds
Li, Hu,Sun, Chang-Liang,Yu, Miao,Yu, Da-Gang,Li, Bi-Jie,Shi, Zhang-Jie
, p. 3593 - 3597 (2011)
From noble to normal: Many transition-metal complexes have shown a remarkable ability to catalyze the cross-coupling of aryl halides with arenes (see scheme). The formation of biaryls has thus been achieved using inexpensive, readily available, and sometimes nontoxic transition-metal complexes. Not only "noble" transition metals, but also many of the "normal" transition metals are able to promote the direct transformation of C-H bonds.
Solid-phase synthesis of biphenyls and terphenyls by the traceless multifunctional cleavage of polymer-bound arenesulfonates
Cho, Chul-Hee,Park, Heon,Park, Min-Ah,Ryoo, Tae-Yong,Lee, Yoon-Sik,Park, Kwangyong
, p. 3177 - 3181 (2005)
Nickel-catalyzed reactions between polymer-bound arene-sulfonates and aryl Grignard reagents produce unfunctionalized biphenyls and terphenyls in good yields through reductive cleavage/cross-coupling of the C-S bond. This novel traceless multifunctional cleavage strategy appears to be a powerful tool for the preparation of large oligophenyl libraries, because it allows the introduction of diversity concomitantly with the release of the target compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
A self-supported palladium-bipyridyl catalyst for the Suzuki-Miyaura coupling in water
Osako, Takao,Uozumi, Yasuhiro
, p. 505 - 514 (2010)
A self-supported palladium catalyst (PdCI2BPy-Cu) was prepared via construction of a metal-organic framework (MOF) of a bipyridyl-palladium complex bearing carboxylic groups and a copper(II) linker. PdCI2BPy-Cu efficiently catalyzed the Suzuki-Miyaura coupling of phenyl halides with arylboronic acids in water under atmospheric conditions to afford the corresponding biaryl products in high yield. The catalyst was reused four times without loss of catalytic activity.
Intermetallic ZrPd3?embedded nanoporous ZrC as an efficient and stable catalyst of the Suzuki cross-coupling reaction
Lu, Yangfan,Ye, Tian-Nan,Park, Sang-Won,Li, Jiang,Sasase, Masato,Abe, Hitoshi,Niwa, Yasuhiro,Kitano, Masaaki,Hosono, Hideo
, p. 14366 - 14374 (2020)
The Suzuki cross-coupling reaction, which is generally catalyzed by Pd-based materials, is a practical approach to create C?C bonds. Although heterogeneous catalysts, including metal-loaded and intermetallic catalysts, afford simple reaction conditions and catalyst reusability, it is challenging to achieve high catalytic activity, durability, and Pd-atom economy together in a single catalyst. Herein, we report the successful preparation of Pd?ZrC, a Pd-based catalyst with the described desirable features. In it, a-few-nanometer-sized nanoparticles of intermetallic ZrPd3 are uniformly dispersed on the surface of nanoporous ZrC with a surface area of 340?450 m2 g?1. As a result of the presence of electron-rich Pd sites and the material’s strong electron-donating ability, Pd?ZrC achieved high catalytic performance in Suzuki cross-coupling reactions at room temperature. Because a low Pd content (1 wt %) is sufficient to produce highly catalytically active Pd?ZrC, this material represents a great improvement in terms of Pd-atom economy over previously reported catalysts. Moreover, no catalytic degradation was noted over up to the presented 15 reaction cycles as the active Pd sites were stabilized in the ZrPd3 lattice. These results indicate that Pd?ZrC has the advantages of both metal-loaded and intermetallic catalysts, providing an approach to enhance the degree of freedom for designing heterogeneous catalysts.
