Ullmann homocoupling of aryl iodides catalyzed by gold nanoparticles stabilized on magnetic mesoporous silica

Rostamizadeh, Shahnaz; Estiri, Hamid; Azad, Mohammad

doi:10.1007/s13738-017-1050-z

Cited by 11 publications

(4 citation statements)

References 27 publications

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“…So far, there have been rather few reports on the Ullmann homocoupling reactions catalyzed by gold nanoparticles [ 75 , 76 ]. The preparation of highly dispersed gold nanoparticles, supported on a magnetic mesoporous silica material, has been reported by Rostamizadeh et al [ 77 ]. The synthesis procedure of the catalyst, reported in a previous paper, included the preparation of (α-Fe 2 O 3 )-MCM41 from a mixture of a magnetic Fe 3 O 4 colloid, sodium silicate, and cetyltrimethylammonium bromide (CTABr), followed by calcination.…”

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 More recently, copper-based catalytic systems have also been replaced by palladium nanoparticles, ionic palladium species, gold nanoparticles, and palladium–gold bimetallic systems.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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“…The reported catalytic systems were magnetically recoverable, reduced reaction time and provided good to excellent yields of the desired compound, as compared to other known catalytic systems for these reactions. The recognized soft interactions of S and Au and the ensuing semi-covalent linkage was exploited by Rostamizadeh et al [174] for designing gold nanoparticle decorated thiol functionalized, hematite encapsulating, MCM-41 (α-Fe 2 O 3 -MCM-41-HSÀ Au) and was used for Ullmann reaction of aryl iodides to yield symmetrical biaryls (Figure 113). The recovered catalyst can be reused in six successive reaction cycles without any significant loss of activity.…”

Section: C-c Coupling Reactionsmentioning

confidence: 99%

Functionalized MCM‐41: Versatile Catalysts for Organic Transformations

et al. 2022

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Functionalized MCM-41 constitute a group of potent hybrid catalysts for organic reactions. Their pore size is large enough to house large substrate molecules, the large bulk of surface silanol groups helps in introduction of a variety of functionalities required for the catalytic action. The current review emphasizes the broad methodology for the synthesis of these catalysts, effect of functionalization on reaction parameters, stability, efficiency, selectivity, reusability along with limitations of these catalysts to organic transformations, from a green chemistry standpoint. Some selected mechanisms of catalytic action are also highlighted. The review demonstrates that surface functionalized MCM-41 constitute innovative and need based catalyst systems that catalyze reactions like Sonogashira, Suzuki, Heck, Friedel Craft reaction, Aldol and Knoevenagel condensation etc. Several other reactions like oxidation, reduction, dehydration, esterification, epoxidation, CÀ S, CÀ N, CÀ O and SÀ S coupling as well as multicomponent synthesis of bioactive heterocycles have also been reported. It is hoped that this review will improve the understanding of scientific community on how these versatile catalysts operate and will provide opportunities to further enhance their utility for chemical industry.

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“…The hydration of a range of alkynes and aliphatic alkyne was investigated to ascertain the scope of the methodology (90-100% of yield). In order to extend the applicability of this catalyst, the authors also reported its catalytic performance in Ullmann homocoupling of aryl iodides to produce symmetrical biaryls [169]. Short reaction time, high selectivity, no observation of undesired side products and utilization of green and magnetically separable catalyst were the advantages of this procedure.…”

Section: Magnetic Mcm-41 To Incorporate Metal Nanoparticlesmentioning

confidence: 99%

mentioning

confidence: 99%

Functionalized Ordered Mesoporous Silicas (MCM-41): Synthesis and Applications in Catalysis

et al. 2018

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Mesoporous silica sieves are among the most studied nano-objects due to their stable pore structure and easy preparation. In particular, MCM-41 have attracted increasing research attention due to their chemical versatility. This review focuses on the synthesis and regioselective functionalization of MCM-41 to prepare catalytic systems. The topics covered are: mono and di-functionalized MCM-41 as basic and acid catalysts, catalysts based on metallic complexes and heteropolyacids supported onto MCM-41, metallic nanoparticles embed onto functionalized MCM-41 and magnetic MCM-41 for catalytic purposes.

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Ullmann homocoupling of aryl iodides catalyzed by gold nanoparticles stabilized on magnetic mesoporous silica

Cited by 11 publications

References 27 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

Functionalized MCM‐41: Versatile Catalysts for Organic Transformations

Functionalized Ordered Mesoporous Silicas (MCM-41): Synthesis and Applications in Catalysis

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