1657-50-7Relevant academic research and scientific papers
On the involvement of palladium nanoparticles in the Heck and Suzuki reactions
Tsvelikhovsky, Dmitry,Popov, Inna,Gutkin, Vitaly,Rozin, Alina,Shvartsman, Azariya,Blum, Jochanan
, p. 98 - 102 (2009)
We describe two different pathways by which palladium-catalyzed Heck and Suzuki coupling reactions take place. When sol-gel entrapped palladium acetate was used as a catalyst, the reactions proceed by the formation of metallic nanoparticles. Such particle
Bimetallic Ni–Pd Synergism—Mixed Metal Catalysis of the Mizoroki-Heck Reaction and the Suzuki–Miyaura Coupling of Aryl Bromides
Kashid, Abhijit A.,Patil, Dharmaraj J.,Mali, Ramling D.,Patil, Vijay P.,Neethu,Meroliya, Heena K.,Waghmode, Shobha A.,Iyer, Suresh
, p. 353 - 358 (2021)
Abstract: A combination of Pd and Ni complexes activated aryl bromides for the thermal Mizoroki-Heck reaction and Suzuki coupling giving high yields in short reaction times. A thermal redox mechanism probably occurs whereby Ni complex transfers electron and reduces the Pd (II) to Pd (0) which then takes the reactants through the standard protocol of oxidative-addition, migratory insertion and reductive elimination, typical for the Mizoroki-Heck reaction and the Suzuki coupling. Graphic Abstract: [Figure not available: see fulltext.]
Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids
Deshmukh,Rajagopal,Srinivasan
, p. 1544 - 1545 (2001)
Heck reaction proceeds at ambient temperature (30 °C) with considerably enhanced reaction rate (1.5-3 h) through the formation of Pd-biscarbene complexes and stabilized clusters of zero-valent Pd nanoparticles in ionic liquids under ultrasonic irradiation.
Mizoroki-Heck carbon-carbon cross-coupling reactions by water-soluble palladium (II) complexes in neat water
Makhubela, Banothile C. E.,Matsinha, Leah C.,Moyo, Pamela S.
supporting information, (2021/08/03)
Water-soluble palladium complexes were synthesized, characterized, tested as (pre)catalyst for Mizoroki-Heck carbon-carbon cross-coupling reactions in water. Cross-coupling of aryl iodides and bromides with methyl and ethyl acrylates was achieved at 140 °
METHODS OF ARENE ALKENYLATION
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Page/Page column 18; 21-22; 42-43; 46, (2021/11/26)
The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).
Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent
Karimi, Sabah,Masteri-Farahani, Majid,Niakan, Mahsa,Shekaari, Hemayat
, (2020/10/02)
Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.
Bimetallic nano alloy architecture on a special polymer: Ni or Cu merged with Pd for the promotion of the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling
Patil, Vijay P,Kashid, Abhijit A,Solanki, Bhanupratap S,Kharul, Ulhas K,Iyer, Suresh
, (2021/02/12)
Abstract: Novel Ni-Pd and Cu-Pd bimetallic nano alloys was designed and heterogenized on the highly robust ABPBI [poly(2,5-benzimidazole)] polymer in high yields using NaBH4 as reducing agent. These were versatile ligand free catalysts for the Mizoroki–Heck reaction and Suzuki–Miyaura coupling. The bimetallic Ni-Pd-ABPBI catalyst for the Mizoroki–Heck reaction of 4-iodo anisole could be recycled 5 times with high yields. Aryl bromides could also be activated for the Mizoroki–Heck reaction using Cu-Pd-ABPBI NP catalysts, with moderate yields. Graphic abstract: Synopsis Novel bimetallic Ni-Pd and Cu-Pd nano alloys, heterogenized on the robust ABPBI [poly(2,5-benzimidazole)] polymer using NaBH4 as reducing agent, is described. These were versatile ligand free, noble metal conservative catalysts, for the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling. Aryl bromides were activated for the Mizoroki–Heck reaction using the Cu-Pd-ABPBI catalyst.[Figure not available: see fulltext.]
Immobilizing palladium on melamine-functionalized magnetic nanoparticles: An efficient and reusable phosphine-free catalyst for Mizoroki–Heck reaction
Aryanasab, Fezzeh,Shabanian, Meisam,Laoutid, Fouad,Vahabi, Henri
, (2021/02/22)
A highly efficient and stable heterogeneous catalyst was successfully prepared by anchoring palladium(0) onto melamine-functionalized Fe3O4 magnetic nanoparticles (MNPs-Mel-Pd). With the aid of amine functional groups, melamine was covalently bonded on epoxy functionalized magnetic nanoparticles and then Pd(0) was immobilized on this support with high dispersion. The prepared nanocatalyst exhibits excellent catalytic activity for C-C cross coupling (Mizoroki–Heck) of various aryl halides (iodide, bromides, and chrlorides) with olefins under mild reaction condition in relatively short reaction times. The synthesized nanocatalyst was characterized using Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), and X-ray photoelectron spectroscopy (XPS) techniques. The loading level of Pd in MNPs-Mel-Pd catalyst was measured to be 1.26 × 10?3 mol g?1 by atomic absorption spectroscopy (AAS). In addition, the catalyst can be easily separated and recovered from the reaction mixture by using an external magnet. The heterogeneity of the catalyst was confirmed by the hot filtration test, which was reused for at least six times under the optimized conditions without any significant loss of its activity.
Transition-Metal-Free Matsuda-Heck Type Cross-Coupling and Mechanistic Evidence for a Radical Mechanism
Bergès, Julien,Zaid, Yassir,Tlili, Anis,Sotiropoulos, Jean-Marc,Taillefer, Marc
supporting information, p. 1559 - 1563 (2021/02/27)
The Matsuda-Heck reaction, usually performed with palladium catalysts, can be carried out under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This system allows the selective and direct synthesis of stilbenes from aryldiazonium salts under mild temperature (20 °C). Mechanistic studies suggest a radical pathway in which the DMF acts as the initiator of the overall process.
Synthesis, crystal structure, and catalytic activity of bridged-bis(N-heterocyclic carbene) palladium(II) complexes in selective Mizoroki-Heck cross-coupling reactions
El Ali, Bassam,Fettouhi, Mohammed,Iali, Wissam,Mansour, Waseem,Suleiman, Rami
, (2021/08/09)
A series of three 1,3-propanediyl bridged bis(N-heterocyclic carbene)palladium(II) complexes (Pd-BNH1, Pd-BNH2, and Pd-BNH3), with + I effect order of the N-substituents of the ligand (isopropyl > benzyl > methoxyphenyl), was the subject of a spectroscopic, structural, computational and catalytic investigation. The bis(NHC)PdBr2 complexes were evaluated in Mizoroki-Heck coupling reactions of aryl bromides with styrene or acrylate derivatives and showed high catalytic efficiency to produce diarylethenes and cinnamic acid derivatives. The X-ray structure of the most active palladium complex Pd-BNH3 shows that the Pd(II) center is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromide ligands in cis position, resulting in a distorted square planar geometry. The NMR data of Pd-BNH3 are consistent with a single chair-boat rigid conformer in solution with no dynamic behavior of the 8-membered ring palladacycle in the temperature range 25–120 °C. The catalytic activities of three Pd-bridged bis(NHC) complexes in the Mizoroki-Heck cross-coupling reactions were not found to have a direct correlation with +I effect order of the N-substituents of the ligand. However, a direct correlation was found between the DFT calculated absolute softness of the three complexes with their respective catalytic activity. The highest calculated softness, in the case of Pd-BNH3, is expected to favor the coordination steps of both the soft aryl bromides and alkenes in the Heck catalytic cycle.
