Suzuki–Miyaura cross-coupling of aryl iodides and phenylboronic acid over palladium-free CeO2 catalysts

Diez, Alejandra Silvina; Graziano-Mayer, Marilyn; Radivoy, Gabriel; Volpe, María Alicia

doi:10.1016/j.apcata.2014.05.020

Cited by 15 publications

(11 citation statements)

References 56 publications

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“…No obvious enhancement in yield was observed by prolonging the reaction time (Table S1, entry 3) or by using a mixed solvent of water and ethanol (Table S1, entry 4). This illustrates that CeO 2 has catalytic activity, but not as the primary catalytic active site required for the Suzuki–Miyaura reaction . Next, we conducted the reaction using Fe 3 O 4 @SiO 2 ‐Pd catalyst with the same solvent, and obtained the desired result, with excellent yield, within three hours (Table S1, entry 5–7).…”

Section: Resultsmentioning

confidence: 97%

“…This illustrates that CeO 2 has catalytic activity,b ut not as the primary catalytic active site required for the Suzuki-Miyaura reaction. [58] Next, we conducted the reactionu sing Fe 3 O 4 @SiO 2 -Pd catalystw ith the same solvent, and obtained the desired result, with excellent yield, within three hours (Table S1,e ntry 5-7). Based on these results, it is clear that the cross-coupling reaction was primarily catalyzed by Pd NPs.…”

Section: Resultsmentioning

confidence: 99%

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Magnetic Core–Shell to Yolk–Shell Structures in Palladium‐Catalyzed Suzuki–Miyaura Reactions: Heterogeneous versus Homogeneous Nature

Zhang

Fan

et al. 2016

ChemPlusChem

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This study describes a comparative investigation on the heterogeneous versus homogeneous nature of the Pd‐catalyzed Suzuki–Miyaura cross‐coupling reaction mechanism with specific magnetic hierarchical core–shell and yolk–shell structures. The hierarchical core–shell Fe3O4@SiO2‐Pd@mCeO2 (m=mesoporous) catalyst contains a core of nonporous silica‐sheltered magnetite (Fe3O4) nanoparticles (NPs), a transition layer of active palladium (Pd) NPs, and an outer shell of porous ceria (CeO2). The magnetic yolk–shell Fe3O4@h‐Pd@mCeO2 (h=hollow) catalyst was prepared by selectively etching the nonporous silica interlayers. Notably, the results of the hot‐filtration heterogeneity test, the effect of Pd concentration, and solid‐phase poisoning, indicate that the two kinds of catalysts function in Pd‐catalyzed Suzuki–Miyaura cross‐coupling reactions through different catalytic mechanisms. Moreover, both catalysts demonstrated better catalytic activity than the Fe3O4@SiO2‐Pd catalyst. This finding can be ascribed to the outermost CeO2 shell having a high concentration of trivalent cerium and oxygen vacancies, which gives rise to the increased electron density of Pd NPs, and a faster rate‐determining step in the oxidative addition reaction for the Suzuki reaction. In addition, we propose a feasible mechanism elucidating the synergistic effect between the supporting CeO2 and active species.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Magnetic Core–Shell to Yolk–Shell Structures in Palladium‐Catalyzed Suzuki–Miyaura Reactions: Heterogeneous versus Homogeneous Nature

Zhang

Fan

et al. 2016

ChemPlusChem

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“…11 In addition to this, ceria has been effectively used as catalyst in various coupling reactions. 12 In continuation, we report the direct C-H arylation reactions using magnetic supported CeO 2 nanoparticles. To the best of our knowledge, use of magnetically separable nano CeO 2 -Fe 3 O 4 catalyst for direct C-H arylation reaction is not yet reported.…”

Section: Introductionmentioning

confidence: 98%

Magnetically separable nano CeO2: a highly efficient catalyst for ligand free direct C–H arylation of heterocycles

Shelkar

Balsane

Nagarkar

2015

Tetrahedron Letters

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“…Keen revision of the literature regarding the heterogeneous catalysts used in Suzuki coupling reaction show that, different types of transition metals were used to catalyse Suzuki coupling reaction. For instance, Volpe and co-workers [3] reported that a series of ceria catalysts used in Suzuki cross-coupling reaction between 4-iodotoluene and phenylboronic acid. The reaction was carried out at 150 ℃, under nitrogen atmosphere and DMF as the solvent which resulting in corresponding biphenyl in high selectivity percentage ( Table 1, Entry 1).…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Novel Efficient Pd-free Catalyst for Suzuki C-C Coupling Reaction

Al-Zhrani¹,

Ahmed²,

Aazam³

et al. 2019

Preprint

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Suzuki cross-coupling reaction has developed one of the furthermost effectual approaches for the synthesis of biaryls or substituted aromatic moieties from aryl halides and arylboronic acids with a palladium-catalyst in the past two era’s. Herein, Pd-free layered double hydroxide containing nickel catalysts were prepared by co-precipitation method under ultrasonic irradiation and N2 atmosphere with different molar ratios of Ni: Mg: Al and coded as (1NiLDHs-Dr), (1.5NiLDHs-Dr) and (2NiLDHs-Dr). A series of reduced catalysts under 5%H2/N2 at different temperatures were coded as 1NiLDHs-R200, 1.5NiLDHs-R200 and 2NiLDHs-R200. As-synthesized 2NiLDHs-Dr was the superlative catalyst when coupling different aryl halides with different boronic acids derivatives. Deep investigation of all catalysts was done using different techniques such as inductively coupled plasma optical emission spectroscopy (ICP-OES), x-ray photoelectron spectroscopy (XPS), powder x-ray diffraction (XRD), thermogravimetric analyses (TGA), Fourier transfer infrared (FTIR), scanning electron microscope (SEM) connected with energy dispersive x-ray (EDX) and N2-physisorption at -196 ℃. The results attained verified that ɑ-Ni(OH)2 was fashioned for 2NiLDHs-Dr catalyst and the enclosure of nickel ions in the cationic sheet of layered structure were responsible for the fascinating catalytic efficacy rather than the basic nature of material. The Ni-containing LDHs catalysts encourage forthcoming studies in Pd-free catalyzed C-C coupling reactions.

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Suzuki–Miyaura cross-coupling of aryl iodides and phenylboronic acid over palladium-free CeO2 catalysts

Cited by 15 publications

References 56 publications

Magnetic Core–Shell to Yolk–Shell Structures in Palladium‐Catalyzed Suzuki–Miyaura Reactions: Heterogeneous versus Homogeneous Nature

Magnetic Core–Shell to Yolk–Shell Structures in Palladium‐Catalyzed Suzuki–Miyaura Reactions: Heterogeneous versus Homogeneous Nature

Magnetically separable nano CeO2: a highly efficient catalyst for ligand free direct C–H arylation of heterocycles

Microwave Assisted Novel Efficient Pd-free Catalyst for Suzuki C-C Coupling Reaction

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