1008-88-4Relevant articles and documents
Newly-generated Al(OH)3-supported Pd nanoparticles-catalyzed Stille and Kumada coupling reactions of diazonium salts, (Het)aryl chlorides
Li, Xing,Zhu, Tingting,Shao, Zhongqi,Li, Yingjun,Chang, Honghong,Gao, Wenchao,Zhang, Yongli,Wei, Wenlong
, p. 69 - 75 (2016)
A ligand-free Pd/Al(OH)3 nano-catalyst which is prepared by one-pot three-component method using Pd(PPh3)4, tetra (ethylene glycol), and aluminum tri-sec-butoxide exhibits excellent catalytic activity in Stille cross-couplings of (Het)aryl chlorides, arenediazonium tetrafluoroborate salts with phenyltributylstannane, respectively, and Kumada couplings of (Het)aryl chlorides with various Grignard reagents. More importantly, these two processes show excellent functional group compatibility with moderate to good yields and they are also versatile with respect to not only (Het)aryl chlorides, but also diazonium salts, and heteroaryl Grignard reagents. The nano-catalyst could also be recycled and reused 5 times without loss of activity and decrease of yield.
Nickel catalyzed cross-coupling and amination reactions of aryl nitriles
Miller, Joseph A.,Dankwardt, John W.,Penney, Jonathan M.
, p. 1643 - 1648 (2003)
Aryl nitriles have been found to participate in cross-coupling and amination reactions via nickel-catalyzed activation of the C-CN bond. With the development of these synthetically useful transformations, aryl nitriles can now be considered along with ary
Pd(OAc)2-catalyzed fluoride-free cross-coupling reactions of arylsiloxanes with aryl bromides in aqueous medium
Shi, Shengyin,Zhang, Yuhong
, p. 5927 - 5930 (2007)
(Chemical Equation Presented) Mild conditions have been developed to achieve the Pd-(OAc)2-catalyzed fluoride-free cross-coupling between the aryl bromides and arylsiloxanes in good to high yields in aqueous medium. The success of the reactions requires the presence of poly(ethylene glycol) (PEG) and 3 equiv of sodium hydroxide. The product was easily separated with ethyl ether extraction, and the catalytic system can be reused eight times with high efficiency.
Three Different Reactions, One Catalyst: A Cu(I) PNP Pincer Complex as Catalyst for C-C and C-N Cross-Couplings
Mastalir, Matthias,Pittenauer, Ernst,St?ger, Berthold,Allmaier, Günter,Kirchner, Karl
, p. 2178 - 2181 (2017)
An air-stable, thermally robust, and well-defined Cu(I) PNP pincer complex based on the 2,6-diaminopyridine scaffold is described. This complex is an active catalyst for the cross-couplings of a range of aryl and heteroaryl (including benzoxazole, thiazole, pyridine, and thiophene) halides with different organomagnesium reagents, alkynes, and aryl-amines giving excellent to good isolated yields.
N-heterocyclic carbene-Pd(II) complex based on theophylline supported on Fe3O4@SiO2 nanoparticles: Highly active, durable and magnetically separable catalyst for green Suzuki-Miyaura and Sonogashira-Hagihara coupling reactions
Esmaeilpour, Mohsen,Sardarian, Ali Reza,Firouzabadi, Habib
, p. 22 - 34 (2018)
In this paper, a novel heterogeneous palladium catalyst was synthesized by anchoring N-heterocyclic carbene-Pd(II) complex based on theophylline on magnetic Fe3O4@SiO2 nanoparticles. The synthesized magnetic composite was characterized by fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA), vibration sample magnetometry (VSM), transmission electron microscopy (TEM), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), N2 adsorption-desorption isotherm analysis (BET), UV–vis spectroscopy and elemental analysis. Also, loading content of palladium on the catalyst was measured by inductive coupled plasma (ICP) analysis. The synthesized catalyst was used successfully for the Suzuki cross-coupling reactions of various aryl halides (I, Br, Cl) with phenylboronic acids. This reaction was best performed in water as a green solvent in the presence of just 0.37–0.5 mol% of the catalyst at 60 °C. Also, we have reported this recyclable catalytic system as a stable phosphine-free Pd catalyst for the Sonogashira cross-coupling of aryl halides (I, Br, Cl) with terminal aromatic and aliphatic alkynes under solvent-free conditions. All coupling reactions proceeded with good to excellent yields. The catalyst showed good stability and was recovered and reused for eight reaction cycles without a significant loss in its catalytic activity. Also, the leaching of the catalyst has been examined by a hot filtration test and ICP-AES analysis.
C-C coupling reactions of aryl bromides and arylsiloxanes in water catalyzed by palladium complexes of phosphanes modified with crown ethers
Gordillo, Alvaro,De Jesus, Ernesto,Lopez-Mardomingo, Carmen
, p. 3517 - 3520 (2006)
The complexes [PdCl2L2], where L is a crown-ether-containing triarylphosphane, catalyze the formation of biaryls from arylsiloxanes and aryl bromides with high yields In water as solvent and under air. The water-insoluble catalysts [PdCl2(PhCN)2] and [PdCl 2(PPh3)2] are also efficient, although they decompose more quickly to form black Pd0.
A pyridine-bridged bis-benzimidazolylidene pincer nickel(ii) complex: Synthesis and practical catalytic application towards Suzuki-Miyaura coupling with less-activated electrophiles
Tu, Tao,Mao, Han,Herbert, Christian,Xu, Mizhi,Doetz, Karl Heinz
, p. 7796 - 7798 (2010)
A novel robust pyridine-bridged bis-benzimidazolylidene nickel pincer complex 3 accessible from inexpensive, commercially available precursors efficiently catalyzes the first practical Suzuki-Miyaura cross-coupling reactions with various less-reactive electrophiles ArX (X = Br, Cl, OTs and OMs) and even tolerates electron-rich, sterically demanding and heterocyclic arenes in the presence of catalytic amounts of PPh3. The Royal Society of Chemistry.
A Polystyrene-Cross-Linking Tricyclohexylphosphine: Synthesis, Characterization and Applications to Pd-Catalyzed Cross-Coupling Reactions of Aryl Chlorides
Arashima, Junya,Iwai, Tomohiro,Sawamura, Masaya
, p. 411 - 415 (2019)
A polystyrene-cross-linking tricyclohexylphosphine (PS-TCP) was synthesized through radical emulsion polymerization of 4-tert-butylstyrene as a monomer and tris(trans-4-styrylcyclohexyl)phosphine as a threefold cross-linker. The PS-TCP showed enhanced ligand performance compared to the corresponding polystyrene-triphenylphosphine hybrid PS-TPP and tricyclohexylphosphine in Pd-catalyzed Suzuki–Miyaura and Buchwald–Hartwig reactions of aryl chlorides.
Leaving Group Ability in Nucleophilic Aromatic Amination by Sodium Hydride-Lithium Iodide Composite
Chiba, Shunsuke,Ong, Derek Yiren,Pang, Jia Hao,Takita, Ryo,Watanabe, Kohei
, p. 393 - 398 (2020)
The methoxy group is generally considered as a poor leaving group for nucleophilic substitution reactions. This work verified the superior ability of the methoxy group in nucleophilic amination of arenes mediated by the sodium hydride and lithium iodide through experimental and computational approaches.
Facile synthesis of highly active Pd-Cu nanowires catalyst through a simple wet-chemical strategy for ligand-free Suzuki cross coupling reaction
Lv, Jing-Jing,Wang, Zheng-Jun,Feng, Jiu-Ju,Qiu, Renhua,Wang, Ai-Jun,Xu, Xinhua
, p. 188 - 193 (2016)
The construction and design of nanomaterials are important for improving their performance. Here we present a simple one-pot wet-chemical method for the preparation of alloyed Pd-Cu nanowires using octylphenoxypolyethoxyethanol (NP-40) as structure-directing and stabilizing agents. The obtained nanocrystals display outstanding catalytic activity for ligand-free Suzuki cross coupling reaction under mild conditions, and can be easily recovered and reused for at least 5 consecutive cycles without showing significant loss of catalytic activity.
