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Synthesis and Characterization of Magnetic Zeolite Y-Palladium-Nickel Ferrite by Ultrasonic Irradiation and Investigating Its Catalytic Activity in Suzuki-Miyaura Cross-Coupling Reactions.

ABSTRACT: Zeolite faujasite is widely used as a catalyst in many industrial catalytic applications. In this study, synthesis and characterization of magnetic zeolite Y-palladium-nickel ferrite were studied. First, palladium nanoparticles were combined with nickel ferrite and then placed on zeolite Y by ultrasonic treatment. The structure and morphology of the synthesized magnetic zeolite Y-palladium-nickel ferrite were characterized using Fourier transform infrared, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray, vibrating sample magnetometer, and inductively coupled plasma optical emission spectroscopy analysis. Also, we investigated the catalytic activity of this prepared zeolite in Suzuki-Miyaura coupling reaction between phenylboronic acid and aryl halides. Our study shows that magnetic zeolite Y-palladium-nickel ferrite is a suitable catalyst for Suzuki-Miyaura coupling reaction. Short reaction time, high yield, and easy reusability are the advantages of using this catalyst in carbon-carbon cross-coupling reactions.

SUBMITTER: Dehghani M

PROVIDER: S-EPMC6647955 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters.

Project description:Transition-metal-catalyzed transformations of amino acids and peptides could provide a powerful method for their site-selective modification. Here, we report non-decarbonylative Pd-catalyzed Suzuki-Miyaura reactions of phenyl ester derivatives of aspartic acid to form aryl-amino ketones. These products are potentially important in the synthesis of pharmaceuticals, and our methodology represents a new route to access molecules of this type.

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Differences in the Performance of Allyl Based Palladium Precatalysts for Suzuki-Miyaura Reactions.

Project description:Palladium(II) precatalysts are used extensively to facilitate cross-coupling reactions because they are bench stable and give high activity. As a result, precatalysts such as Buchwald's palladacycles, Organ's PEPPSI species, Nolan's allyl-based complexes, and Yale's 1-tert-butylindenyl containing complexes, are all commercially available. Comparing the performance of the different classes of precatalysts is challenging because they are typically used under different conditions, in part because they are reduced to the active species via different pathways. However, within a particular class of precatalyst, it is easier to compare performance because they activate via similar pathways and are used under the same conditions. Here, we evaluate the activity of different allyl-based precatalysts, such as (η3-allyl)PdCl(L), (η3-crotyl)PdCl(L), (η3-cinnamyl)PdCl(L), and (η3-1-tert-butylindenyl)PdCl(L) in Suzuki-Miyaura reactions. Specifically, we evaluate precatalyst performance as the ancillary ligand (NHC or phosphine), reaction conditions, and substrates are varied. In some cases, we connect relative activity to both the mechanism of activation and the prevalence of the formation of inactive palladium(I) dimers. Additionally, we compare the performance of in situ generated precatalysts with commonly used palladium sources such as tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3), bis(acetonitrile)dichloropalladium(II) (Pd(CH3CN)2Cl2), and palladium acetate. Our results provide information about which precatalyst to use under different conditions.

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Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions.

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Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki-Miyaura Coupling Reactions.

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Bis(dialkylphosphino)ferrocene-Ligated Nickel(II) Precatalysts for Suzuki-Miyaura Reactions of Aryl Carbonates.

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DFT Investigation of Suzuki-Miyaura Reactions with Aryl Sulfamates Using a Dialkylbiarylphosphine-Ligated Palladium Catalyst.

Project description:Aryl sulfamates are valuable electrophiles for cross-coupling reactions because they can easily be synthesized from phenols and can act as directing groups for C-H bond functionalization prior to cross-coupling. Recently, it was demonstrated that (1-tBu-Indenyl)Pd(XPhos)Cl (XPhos = 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) is a highly active precatalyst for room-temperature Suzuki-Miyaura couplings of a variety of aryl sulfamates. Herein, we report an in-depth computational investigation into the mechanism of Suzuki-Miyaura reactions with aryl sulfamates using an XPhos-ligated palladium catalyst. Particular emphasis is placed on the turnover-limiting oxidative addition of the aryl sulfamate C-O bond, which has not been studied in detail previously. We show that bidentate coordination of the XPhos ligand via an additional interaction between the biaryl ring and palladium plays a key role in lowering the barrier to oxidative addition. This result is supported by NBO and NCI-Plot analysis on the transition states for oxidative addition. After oxidative addition, the catalytic cycle is completed by transmetalation and reductive elimination, which are both calculated to be facile processes. Our computational findings explain a number of experimental results, including why elevated temperatures are required for the coupling of phenyl sulfamates without electron-withdrawing groups and why aryl carbamate electrophiles are not reactive with this catalyst.

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Nickel-catalyzed Suzuki-Miyaura couplings in green solvents.

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| S-EPMC3768281 | biostudies-literature

Nickel-catalyzed Suzuki-Miyaura cross-couplings of aldehydes.

Project description:Transition-metal-catalyzed cross-couplings have been extensively used in the pharmaceutical and agrochemical industries for the construction of diverse C-C bonds. Conventional cross-coupling reactions require reactive electrophilic coupling partners, such as organohalides or sulfonates, which are not environmentally friendly and not naturally abundant. Another disadvantage associated with these transformations is the need for an exogenous base to facilitate the key transmetalation step, and this reagent inevitably induces side reactions and limits the substrate scope. Here, we report an unconventional Suzuki-type approach to the synthesis of biaryls, through nickel-catalyzed deformylative cross coupling of aldehydes with organoboron reagents under base-free conditions. The transformation tolerates structurally diverse (hetero)aryl substituents on both coupling partners and shows high reactivity and excellent functional group tolerance. Furthermore, the protocol was carried out on gram scale and successfully applied to the functionalization of complex biologically active molecules. Mechanistic investigations support a catalytic cycle involving the oxidative addition of the nickel into the aldehyde C(acyl)-H bond with subsequent hydride transfer, transmetalation, decarbonylation and reductive elimination processes.

| S-EPMC6488620 | biostudies-literature

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