A Pd(II) complex of a <i>β</i>-cyclodextrin-based polydentate ligand: an efficient catalyst for the Suzuki reaction in aqueous media

Das, Ananya; Mishra, Dipu Kumar; Sinha, Biswajit

doi:10.1080/00958972.2017.1378812

Cited by 15 publications

(5 citation statements)

References 41 publications

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“…In similar lines, in 2017 Sinha and co-workers reported their studies on the obtainment of a supramolecular polydentate complex from β-CD and 2,6-diaminopyridine using as medium an ionic liquid prepared with β-CD and choline bromide, and the use of this catalytic system in the Suzuki reaction. [57] In 2018, Yang, Jin, Lin and co-workers reported the synthesis of new picolinamine-modified β-CD ligands (43 and 44, Figure 1) and the application of their Pd complexes as catalysts in the Suzuki reaction. [58] The complexes obtained from 43 and 44 were evaluated in the Suzuki reaction of 4-bromoacetophenone, cinnamyl bromide and benzyl bromide with 4-methylphenylboronic acid, and in all cases, the complex derived from 44 led to the highest yield, with the one derived from 43 giving significantly lower yields, which was attributed to a mismatch between the catalytic metal center and the hydrophobic cavity of the β-CD.…”

Section: Pd-cyclodextrin Complexes As Catalystsmentioning

confidence: 99%

Supramolecular Catalysts for Organic Synthesis: Preparation and Applications of Cyclodextrins and Calixarenes in C−C Cross‐Coupling Reactions

et al. 2022

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Reactions that promote the formation of carbon-carbon bonds are of great importance in organic synthesis, since they transform available, relatively inexpensive, and small organic molecules into more complex ones. One of the main protocols used for these transformations are cross-coupling reactions, and due to their versatility and applications, several efforts have been devoted recently to developing catalysts for such reactions. Supramolecular chemistry has become a major player in this field and encompasses approaches that range from the synthesis of intricate complex architectures that may mimic enzymes, the slight structural modification of commercially available scaffolds, or even repurposing highly available materials such as agarose. This Review discusses the development of supramolecular catalysts for cross-coupling reactions, focusing mostly on the Suzuki, Heck and Sonogashira reactions promoted by such assemblies.

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Section: Pd-cyclodextrin Complexes As Catalystsmentioning

confidence: 99%

Supramolecular Catalysts for Organic Synthesis: Preparation and Applications of Cyclodextrins and Calixarenes in C−C Cross‐Coupling Reactions

et al. 2022

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“…Sinha and coworkers reacted βCD with choline bromide to form a βCD-ionic liquid derivative. [137] Further treatment with 2,6-diaminopyridine resulted in the formation of a 1 : 1 inclusion complex which, after loading with Pd, gave water-soluble catalyst material Pd(OAc) 2 :63-βCD. Medium to high activities were recorded in aqueous solution at room temperature (Scheme 24) with significant activity losses in four reuses.…”

Section: The Use Of Pd 2 + Complexesmentioning

confidence: 99%

“…yield 90.5 %). Sinha and coworkers reacted βCD with choline bromide to form a βCD–ionic liquid derivative [137] . Further treatment with 2,6‐diaminopyridine resulted in the formation of a 1 : 1 inclusion complex which, after loading with Pd, gave water‐soluble catalyst material Pd(OAc) 2 :63 ‐βCD.…”

Section: Coupling Reactionsmentioning

confidence: 99%

Synthetic Application of Cyclodextrins in Combination with Metal Ions, Complexes, and Metal Particles

Molnár

2020

ChemCatChem

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Cyclodextrins are green, environmentally benign products available through the enzymatic degradation of starch for a multitude of varied applications. This review attempts to collect useful information with respect to catalytic studies performed with the use of cyclodextrin and modified cyclodextrin preparations applied in combination of or loaded with varied catalytically active species including metal ions, complexes, and metal particles. Major sections are about their use in hydrogenation, reduction, oxidation, hydroformylation and coupling reactions. Additional sections include their utilization in ring formation and ring opening as well as degradation of pollutants. In the last part, examples about ester hydrolysis, hydroboration and hydrosilylation, as well as hydrogen production are treated. Data collected and analyzed indicate the importance and high potential of cyclodextrin-based catalysts in sustainable chemistry.

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“…Various catalysts based on β-CD have recently been developed for Suzuki-Miyaura coupling reactions. [36][37][38][39][40][41][42] Designing and developing a novel 44 introduced the PdLn@Et-β-CD as a beneficial catalyst in the water Suzuki reaction. PdLn@Et-β-CD made of aminoethylamino-β-CD-supported palladium complex (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

“…The β‐CDs catalytic system had good stability and could be recycled and reused with no significant drop in activity. Various catalysts based on β‐CD have recently been developed for Suzuki–Miyaura coupling reactions 36–42 . Designing and developing a novel and effective protocol for forming β‐CD‐based catalysts with high catalytic performance, recoverability, low price, high catalyst stability, and simple workup is attractive.…”

Section: Introductionmentioning

confidence: 99%

The recent development of β‐cyclodextrin‐based catalysts system in Suzuki coupling reactions

Payamifar,

Abdouss,

Poursattar Marjani

2024

Applied Organom Chemis

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β‐Cyclodextrin has drawn significant attention as a special class of cyclic oligomers over the past few decades. They have been employed in many organic conversions as green alternative catalysts to perform satisfactorily in catalytic activity and modify the efficiency of organic reactions. Its availability, nontoxicity, low cost, renewability, and high performance in organic transformations are several benefits of cyclodextrins that have captured the interest of many research groups worldwide. In recent decades, great progress has been made in developing metal‐catalyzed coupling reactions to create carbon–carbon bonds. For the transition‐metal‐catalyzed cross‐coupling, using modified β‐cyclodextrin derivatives as catalysts is much more pleasant due to the obvious advantages such as valuable catalytic properties and the capability to create an inclusion complex with different metals. The particular purpose of this review is to summarize the application of β‐cyclodextrin‐based catalyst systems in Suzuki coupling reaction for the synthesis of biaryl compounds covering the years 2019–2023.

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A Pd(II) complex of a β-cyclodextrin-based polydentate ligand: an efficient catalyst for the Suzuki reaction in aqueous media

Cited by 15 publications

References 41 publications

Supramolecular Catalysts for Organic Synthesis: Preparation and Applications of Cyclodextrins and Calixarenes in C−C Cross‐Coupling Reactions

Supramolecular Catalysts for Organic Synthesis: Preparation and Applications of Cyclodextrins and Calixarenes in C−C Cross‐Coupling Reactions

Synthetic Application of Cyclodextrins in Combination with Metal Ions, Complexes, and Metal Particles

The recent development of β‐cyclodextrin‐based catalysts system in Suzuki coupling reactions

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