720-75-2Relevant articles and documents
Palladium nanoparticles in carbon thin film-lined SBA-15 nanoreactors: Efficient heterogeneous catalysts for Suzuki-Miyaura cross coupling reaction in aqueous media
Zhi, Jian,Song, Depeng,Li, Zhiwen,Lei, Xia,Hu, Aiguo
, p. 10707 - 10709 (2011)
Embedding Pd nanoparticles in carbon thin film-lined SBA-15 nanoreactors provides highly efficient catalysts for heterogeneous cross coupling reactions in aqueous media. No leaching or aggregation of Pd nanoparticles was found in these nanoreactors after reusing them several times. The carbon thin film lining of these nanoreactors was further confirmed with small molecular arene probing experiments.
A Thiol-Functionalized UiO-67-Type Porous Single Crystal: Filling in the Synthetic Gap
Wong, Yan-Lung,Diao, Yingxue,He, Jun,Zeller, Matthias,Xu, Zhengtao
, p. 1462 - 1468 (2019)
Thiol groups (-SH) offer versatile reactivity for functionalizing metal-organic frameworks, and yet thiol-equipped MOF solids remain underexplored due to synthetic challenges. Building on the recent breakthrough using benzyl mercaptan as the sulfur source and AlCl3 for uncovering the thiol function, we report on the thiol-equipped linker 3,3′-dimercaptobiphenyl-4,4′-dicarboxylic acid and its reaction with Zr(IV) ions to form a UiO-67-type MOF solid with distinct functionalities. The thiol-equipped UiO-67 scaffold shows substantial stability toward oxidation, e.g., it can be treated with 30% H2O2 to afford oxidation of the thiol to the strongly acidic sulfonic function while maintaining the ordered porous MOF structure. The thiol groups also effectively take up palladium(II) ions from solutions to allow for comparative studies on catalytic activities and to help elucidate how the spatial configuration of the thiol groups can be engineered to impact the performance of heterogeneous catalysis in the solid state. Comparative studies on the stability in the solventless (activated) state also help to highlight the steric factor in stabilizing UiO-67-type frameworks.
Palladium supported on mesoporous silica via an in-situ method as an efficient catalyst for Suzuki-Miyaura coupling reactions
Wang, Peiyu,Zhang, Guoheng,Liu, Liwei,Jiao, Haiyan,Deng, Xiaoyan,Zheng, Xiaoping
, p. 365 - 369 (2014)
Palladium-containing SBA-15 (Pd/SBA-15) was synthesized via an in situ approach. In this procedure, the hydrophobic solvent (CHCl3) was used as a transport medium to inject the Pd precursor (Pd(acetylacetonate) 2) directly into the inner core of the surfactant micelles. The resulting nanocomposite with 1.46 wt% Pd loading was achieved with highly dispersed and uniform palladium nanoparticles. The Pd/SBA-15 nanocomposite exhibited excellent catalytic activities and reuse ability in air for the Suzuki-Miyaura coupling reactions.
Transition-metal-free Suzuki-type coupling reactions
Leadbeater, Nicholas E.,Marco, Maria
, p. 1407 - 1409 (2003)
No metal required: The first transition-metal-free Suzuki-type coupling reaction was carried out in water by using tetrabutylammonium bromide (TBAB) as an additive (see scheme). Products were obtained in high yields with a wide range of aryl bromide substrates.
Nickel-Catalyzed Carbonylation of Difluoroalkyl Bromides with Arylboronic Acids
Zhao, Hai-Yang,Gao, Xing,Zhang, Shu,Zhang, Xingang
, p. 1031 - 1036 (2019)
A nickel-catalyzed carbonylative difluoroalkylation reaction with arylboronic acids under 1 atm of CO has been developed. The reaction proceeds under mild reaction conditions with high efficiency and high functional group tolerance. Preliminary mechanistic studies reveal that the arylacyl nickel complex is the key intermediate to circumvent the formation of labile fluoroacyl nickel, and bimetallic oxidative addition is likely the key step to facilitate the catalytic cycle.
Recycling Oryza sativa wastes into poly-imidazolium acetic acid-tagged nanocellulose Schiff base supported Pd nanoparticles for applications in cross-coupling reactions
Elshaarawy, Reda F. M.,Yahya, Rana
, (2021/12/22)
A green and sustainable heterogeneous nanocatalyst for the Suzuki reaction was fabricated by refining rice straw to ionic nanocellulose Schiff base (NCESB) which was employed for bio-reduction of Pd(II) into Pd nanoparticles (Pd NPs) and immobilization of these NPs to fabricate the desired nanocatalyst (NCESB@Pd). The TEM image revealed well-dispersed PdNPs with sizes of 5–23 nm. The new nanocatalyst displayed amazing activity in catalyzing coupling reactions of a wide range of halobenzenes with phenylboronic acid at 50 °C (reaction time 15–60 min) and even at room temperature (reaction time 120 min). The NCESB@Pd nanocatalyst exhibited excellent recyclability (up to five catalytic runs) without a significant loss of its activity or identity. Therefore, the new ionic nanocatalyst may open a new window for a novel generation of ionic low-cost green and highly effective nanocatalysts for organic transformation reactions.
Irradiation with UV Light Accelerates the MigitaKosugiStille Coupling Reaction in Air
Ishikawa, Takumi,Iwai, Tomohiro,Masai, Hiroshi,Murata, Mako,Terao, Jun
supporting information, p. 124 - 126 (2022/02/14)
The Migita-Kosugi-Stille coupling reaction is a powerful method for the formation of carboncarbon bonds but often requires high temperatures that are not tolerated by all substrates. Herein, we report that irradiation with UV light accelerates this coupling reaction at room temperature in air in the presence of the commercially available PdCl2(PPh3)2 catalyst. This UVlight- assisted coupling reaction requires the presence of molecular oxygen, with mechanistic studies revealing that singlet oxygen is most likely involved in the reaction.
2-Phosphinoimidazole Ligands: N-H NHC or P-N Coordination Complexes in Palladium-Catalyzed Suzuki-Miyaura Reactions of Aryl Chlorides
Martinez, Erin E.,Larson, Alexandra J. S.,Fuller, Sydney K.,Petersen, Kathryn M.,Smith, Stacey J.,Michaelis, David J.
supporting information, p. 1560 - 1564 (2021/05/29)
We report the synthesis of two palladium 2-(dialkylphosphino)imidazole complexes and demonstrate their activity as catalysts for Suzuki-Miyaura reactions with (hetero)aryl chlorides at room temperature. Our mechanistic studies demonstrate that these palladium complexes exist as an equilibrium mixture between the P-N coordinated and N-H NHC forms of ligand. Our studies suggest that the N-H NHC form may be important for high catalytic activity in Suzuki-Miyaura reactions with aryl chlorides. These reactions proceed at or near room temperature in good to excellent yields. Heteroaryl chlorides are also reactive at lower catalyst loadings.
