292625-97-9Relevant articles and documents
A ferrocene based palladacyclic precatalyst for the Suzuki cross-coupling of aryl chlorides
Roca, Francesc X.,Richards, Christopher J.
, p. 3002 - 3003 (2003)
Addition of palladium acetate to 2-(dicyclohexylphosphino)-phenylferrocene gave palladacycle 16 that is a very effective precatalyst for the Suzuki cross-coupling of aryl chlorides at room temperature (1 mol% 16) or 60°C (≥ 0.01 mol% 16).
Synthesis, characterization, and reactivity of palladium(II) complexes containing piperidoimidazolin-2-ylidene
Tuerkmen, Hayati,Kani, Ibrahim
, p. 489 - 493 (2013)
A series of Pd-N-heterocyclic carbene (Pd-NHC) complexes with pyrazine (1) or pyridine (2) and NHC (3) were synthesized and characterized by elemental analysis and spectroscopic methods. In addition, the molecular structure of 3 was determined by X-ray diffraction studies. The effects of these ligands on catalyst activation and the performance of complexes 1-3 were studied on Suzuki-Miyaura reactions of phenylboronic acid with aryl chlorides. Finally, we demonstrated that complex 1 is very adept at re-forming the Kumada-Tamao-Corriu cross-coupling reaction. Copyright
Alkali-metal-mediated manganation(II) of functionalized arenes and applications of ortho-manganated products in Pd-catalyzed cross-coupling reactions with iodobenzene
Blair, Victoria L.,Clegg, William,Conway, Ben,Hevia, Eva,Kennedy, Alan,Klett, Jan,Mulvey, Robert E.,Russo, Luca
, p. 65 - 72 (2008)
Extending the recently introduced concept of "alkali-metal-mediated manganation" to functionalised arenes, the heteroleptic sodium manganate reagent [(tmeda)Na(tmp)(R)Mn(tmp)] (1; TMEDA = N,N,N′,N′-tetra- methylethylenediamine, TMP = 2,2.6,6-tetramethylpiperidide, R = CH 2SiMe3) has been treated with anisole or N,N-diisopropylbenzamide in a 1:1 stoichiometry in hexane. These reactions afforded the crystalline products [(tmeda)Na(tmp)(o-C6H 4OMe)Mn-(tmp)] (2) and [(tmeda)Na(tmp){o(C(O)N(iPr)2C 6H4)Mn(CH2SiMe3)] (3), respectively, as determined from X-ray crystallography studies. On the basis of these products, it can be surmised that reagent 1 has acted, at least partially and ultimately, as an alkyl base in the first reaction liberating the silane Me 4Si, but as an amido base in the second reaction liberating the amine TMPH. Both of these paramagnetic products 2 and 3 have contacted ion-pair structures, the key features of which are six-atom, five-element (NaNMnCCO) and seven-atom, five-element (NaNMnCCCO) rings, respectively. Manganates 2 and 3 were successfully cross-coupled with iodobenzene under [PdCl2(dppf)] (dppf = 1,1′-bis(diphenylphosphino)ferrocene) catalysis to generate unsymmetrical biaryl compounds in yields of 98.0 and 66.2%, respectively. Emphasizing the importance of alkali-metal mediation in these manganation reactions, the bisalkyl Mn reagent on its own fails to metalate the said benzamide, but instead produces the monomeric, donoracceptor complex [Mn(R) 2{(iPr)2-NC(Ph)(=O)}2] (5), which has also been crystallographically characterised. During one attempt to repeat the synthesis of 2, the butoxide-contaminated complex [{(tmeda)Na(R)(OBu)(o-C 6H4OMe)Mn}2] (6) was obtained. In contrast to 2 and 3, due to reduced steric constraints, this complex adopts a dimeric arrangement in the crystal, the centrepiece of which is a twelve atom (NaOCCMnC)2 ring.
Eumelanin as a support for efficient palladium nanoparticle catalyst for Suzuki coupling reaction of aryl chlorides in water
Kim, Young-O,You, Jae Myoung,Jang, Hyung-Seok,Choi, Seo Keong,Jung, Byeong Yun,Kang, Onyu,Kim, Jung Won,Lee, Yoon-Sik
, p. 2149 - 2152 (2017)
Eumelanin-supported palladium (Pd) nanoparticle (NP) catalysts was found to exhibit excellent catalytic activities with high turnover number (TON, 2000) and turnover frequency (TOF, 1000?h?1) for Suzuki cross coupling reaction of aryl chlorides in water. We propose that the amphiphilic property of the eumelanin support helps Pd NPs to catalyse the C–C coupling reaction in water through hydrophobic effect.
Encapsulation of palladium chloride using 2-formylbenzoic acid supported by Fe3O4 nanoparticles modified with SiO2 and propylamine, its characterization and its application for Suzuki coupling reaction
Mostafavi, Hamid,Islami, Mohammad Reza,Momeni Tikdari, Ahmad
, (2018)
A magnetically separable heterogeneous nanocatalyst, Fe3O4@SiO2(CH2)3N―CH―Ar@Pd(0), was simply prepared and characterized using various techniques. The catalytic activity of this nanocatalyst was evaluated via the Suzuki–Miyaura cross-coupling reaction of aryl halides with phenylboronic acid under various experimental conditions such as kind of base, solvent and temperature. This nanocatalyst is completely magnetically recoverable because of the superparamagnetic behaviour of Fe and can be reused with sustained selectivity and activity.
Transition metal catalyzed cross-coupling of aryl Grignard reagents with aryl fluorides via Pd- or Ni-activation of the C-F bond: An efficient synthesis of unsymmetrical biaryls - Application of microwave technology in ligand and catalyst screening
Dankwardt, John W.
, p. 932 - 938 (2005)
Biaryl compounds are prevalent in both nature and in active pharmaceutical ingredients. The palladium and nickel catalyzed cross-coupling of aryl Grignard reagents with aryl fluorides reported herein affords moderate to excellent yields of the corresponding unsymmetrical biaryls. In addition, the first example of a biaryl cross-coupling utilizing unactivated aryl fluorides under phosphine free palladium conditions is reported. Microwave technology allowed rapid optimization of catalyst systems, which identified several ligands for this cross-coupling reaction.
Palladium nanoparticles supported on amino functionalized metal-organic frameworks as highly active catalysts for the Suzuki-Miyaura cross-coupling reaction
Huang, Yuanbiao,Zheng, Zhaoliang,Liu, Tianfu,Lü, Jian,Lin, Zujin,Li, Hongfang,Cao, Rong
, p. 27 - 31 (2011)
Well dispersed Pd nanoparticles supported on amino functionalized metal-organic frameworks MIL-53(Al)-NH2 (Al(OH)[H2N-BDC], H2N-BDC = 2-aminoterephthalic acid, MIL = Materials of Institut Lavoisier) were prepared using a direct anionic exchange approach and subsequent reduction with NaBH4. The Pd/MIL-53(Al)-NH2 catalyst exhibitted high activity and good stability for Suzuki-Miyaura cross-coupling reaction.
Synthesis of Pd immobilized on functionalized hexagonal mesoporous silica (HMS–CPTMS–Cy–Pd) for coupling Suzuki–Miyaura and Stille reactions
Gholamian, Fatemeh,Hajjami, Maryam
, p. 649 - 658 (2019)
In this paper, Pd–cytosine complex immobilized on functionalized hexagonal mesoporous silica (HMS–CPTMS–Cy–Pd) as a novel mesoporous catalyst with high activity for the Stille and Suzuki coupling reactions was successfully fabricated. All products were obtained in good to excellent yields at low time reaction. The prepared catalyst has been characterized using various techniques such as FT-IR, XRD, BET, SEM, EDX-MAP, TGA and ICP. Recovery test confirm that the synthesized catalyst can be able to reuse for several times.
Bentonite clay as an efficient substrate for the synthesis of the super stable and recoverable magnetic nanocomposite of palladium (Fe3O4/Bentonite-Pd)
Bananezhad, Behjat,Islami, Mohammad Reza,Ghonchepour, Ehsan,Mostafavi, Hamid,Tikdari, Ahmad Momeni,Rafiei, Hamid Reza
, p. 192 - 200 (2019)
Bentonite has a potential for the catalytic carrier because their surface and special structure are very suitable for supporting transition metals. This clay as a nontoxic, inexpensive, freely available and abundant natural mineral was used to synthesize magnetic nanocomposite of palladium as a super stable and recoverable green catalyst (Fe3O4/Bentonite-Pd). The catalytic activity of this system was evaluated in the Suzuki cross-coupling reaction. Determination of novel nanoparticles structure was performed using FT‐IR, XRD, VSM, TGA, and SEM–EDX spectral data.
Starch assisted palladium(0) nanoparticles as in situ generated catalysts for room temperature Suzuki-Miyaura reactions in water
Dewan, Anindita,Bharali, Pankaj,Bora, Utpal,Thakur, Ashim Jyoti
, p. 11758 - 11761 (2016)
A simple and efficient methodology for the in situ generation of Pd-nanoparticles in the presence of starch and NaOH at room temperature has been developed. It has been observed that starch played a dual role in controlling the reduction rate of metal ions and the aggregation process of metal atoms in solution. The in situ generated Pd-nanoparticles show excellent catalytic activity in the Suzuki-Miyaura cross coupling reaction of electronically diversified arylbromides and arylboronic acids in pure water at room temperature with low catalyst loading.
