Palladium Immobilized onto Functionalized Magnetic Nanoparticles as Robust Catalysts for Amination and Room‐Temperature Ullmann Homocoupling of Aryl Halides: A Walk Around the C−F Bond Activation

Moghaddam, Firouz Matloubi; Pourkaveh, Raheleh; Karimi, Ashkan; Ayati, Seyed Ebrahim

doi:10.1002/ajoc.201800041

Cited by 7 publications

(3 citation statements)

References 29 publications

(26 reference statements)

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“…As related to the remarkable thermal and chemical stability of organofluorine compounds, transition metal-catalyzed C–F bond transformations have been investigated less frequently [ 34 ]. Moghadamm et al reported on the Ullmann homocoupling of unactivated aryl halides, including fluorobenzene, performed by using a novel magnetic heterogeneous palladium catalyst, synthesized by immobilization of palladium onto aminopyridine-functionalized Fe 3 O 4 particles [ 35 ]. Magnetic Fe 3 O 4 nanoparticles, obtained from FeCl 3 and FeCl 2 by co-precipitation, were used for the synthesis of Fe 3 O 4 -silica-coated nanoparticles, which were treated with 3-glycidyl(oxypropyl)trimethoxysilane, followed by the addition of 2-aminopyridine.…”

Section: Resultsmentioning

confidence: 99%

A Novel Insight into the Ullmann Homocoupling Reactions Performed in Heterogeneous Catalytic Systems

Mastalir

Molnár

2023

Molecules

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The Ullmann reaction has been reported to be the first cross-coupling reaction performed by using a transition metal catalyst. This reaction has been initially considered as the copper-catalyzed homocoupling of aryl halides, leading to the formation of symmetrical biaryl compounds via the generation of novel C–C bonds. Although this reaction has been extensively studied in recent decades and valuable results have been achieved, there are still considerable efforts focused on the development of novel catalytic systems, mild reaction conditions, and extended substrate scope. The mechanistic aspects of the Ullmann homocoupling reaction have also been investigated, as related to the introduction of new sustainable strategies and green procedures. The application of recyclable heterogeneous catalysts has been found to overcome most of the limitations associated with the harsh reaction conditions of the original Ullmann reaction. More recently, copper-based catalytic systems have also been replaced by palladium nanoparticles, ionic palladium species, gold nanoparticles, and palladium–gold bimetallic systems. In this review, current results reported on the Ullmann homocoupling reaction are discussed, with an emphasis on the development of novel catalytic systems, which can be efficiently used under heterogeneous conditions.

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Section: Resultsmentioning

confidence: 99%

A Novel Insight into the Ullmann Homocoupling Reactions Performed in Heterogeneous Catalytic Systems

Mastalir

Molnár

2023

Molecules

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“…However, the traditional Ullmann coupling reaction has been carried out under harsh reaction conditions, such as high temperature, extended reaction times, use of toxic solvents, and strong bases [ 13 , 14 ]. Despite extensive research on Ullmann coupling reactions, there remains a significant scope to explore recoverable catalysts, mild reaction conditions, and a wider substrate range in this field [ 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis Hyper-Crosslinked PdFe Bimetallic Polymer as Highly Active Catalyst for Ullmann Coupling Reaction of Chlorobenzene

et al. 2023

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The synthesis of efficient and sustainable heterogeneous Pd-based catalysts has been an active field of research due to their crucial role in carbon–carbon coupling reactions. In this study, we developed a facile and eco-friendly in situ assembly technique to produce a PdFe bimetallic hyper-crosslinked polymer (HCP@Pd/Fe) to use as a highly active and durable catalyst in the Ullmann reaction. The HCP@Pd/Fe catalyst exhibits a hierarchical pore structure, high specific surface area, and uniform distribution of active sites, which promote catalytic activity and stability. Under mild conditions, the HCP@Pd/Fe catalyst is capable of efficiently catalyzing the Ullmann reaction of aryl chlorides in aqueous media. The exceptional catalytic performance of HCP@Pd/Fe is attributed to its robust absorption capability, high dispersion, and strong interaction between Fe and Pd, as confirmed by various material characterizations and control experiments. Furthermore, the coated structure of a hyper-crosslinked polymer enables easy recycling and reuse of the catalyst for at least 10 cycles without any significant loss of activity.

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“…Thus, it is crucial to develop environmentally benign and cost-effective heterogeneous catalysts. Significant efforts have been devoted to the synthesis of catalysts in which Pd is supported on solid matrices such as functional organic polymers (Nasrollahzadeh et al 2020;Rafiee 2019;Karimi et al 2010;Kann 2010;Kumbhar and Salunkhe 2015), silicas (Khodaei and Dehghan 2019), zeolites (Chai et al 2019), carbonaceous materials (Nasrallah and Hierso 2019), and magnetic nanoparticles (Moghaddam et al 2018) (Wang et al 2019;Nasrollahzadeh et al 2017). However, preventing the continuous loss of the catalytic metal from the heterogeneous catalysts during the reactions remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of palladium supported on mesoporous hydroxyapatite from oyster shells for use as efficient, green, and recyclable catalyst for Heck reactions

et al. 2021

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catalyst was synthesized by the immobilization of Pd on hydroxyapatite obtained by the hydrothermal method using naturally abundant oyster shells as the calcium source, ammonium dibasic phosphate as the phosphorus source, and cetyltrimethylammonium bromide as the porogen. The synthesized heterogeneous catalyst was characterized using N 2 -physisorption (adsorptiondesorption) measurements, X-ray diffraction analysis, X-ray photoelectron spectroscopy, inductively coupled plasma mass spectrometry, transmission electron microscopy, and temperature-programmed reduction and desorption measurements. The Pd/HAP catalyst shows high catalytic activity for the cross-coupling reaction between iodobenzene and olefins, resulting in yields greater than 67%. Moreover, the Pd/HAP catalyst could be recycled and reused six times with slight reduction in the yield, and thus, is highly stable and recyclable. In addition, it is suitable for use in Heck cross-coupling reactions between various aryl halides and alkenes. Thus, the synthesized catalyst should find extensive use in synthetic chemistry.

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Palladium Immobilized onto Functionalized Magnetic Nanoparticles as Robust Catalysts for Amination and Room‐Temperature Ullmann Homocoupling of Aryl Halides: A Walk Around the C−F Bond Activation

Cited by 7 publications

References 29 publications

A Novel Insight into the Ullmann Homocoupling Reactions Performed in Heterogeneous Catalytic Systems

A Novel Insight into the Ullmann Homocoupling Reactions Performed in Heterogeneous Catalytic Systems

Facile Synthesis Hyper-Crosslinked PdFe Bimetallic Polymer as Highly Active Catalyst for Ullmann Coupling Reaction of Chlorobenzene

Synthesis of palladium supported on mesoporous hydroxyapatite from oyster shells for use as efficient, green, and recyclable catalyst for Heck reactions

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