A new thioglycolic ester β-cyclodextrin/PdCl2 in water: An accessible catalyst for the Suzuki-Miyaura coupling reaction

Souza, Viviane Costa de; Ramos, Gabriel dos Santos; Leite, Juliana Lago; Santos, Mauricio Brandão dos; Otubo, Larissa; Camargo, Zaine Teixeira; Victor, Maurício M.

doi:10.1016/j.carbpol.2022.120271

Cited by 8 publications

(4 citation statements)

References 40 publications

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“…The catalytic performance of recently reported water-soluble Pd catalysts in the Suzuki-Miyaura coupling reaction was compared with respect to reaction conditions and yields (Table S4). A variety of catalyst systems such as Pd complexes of functionalized N-heterocyclic carbene, ,− cyclodextrin derivatives, − sulfonated ligands − and Quadrol, and Pd-nanocluster , were explored. The results show that the present catalysts perform comparable activity with respect to the high yield in pure water.…”

Section: Resultsmentioning

confidence: 99%

Linkage Isomers of Triangular Pd Metallacycles and Catalysis in Aqueous Suzuki Coupling Reaction

Chaudhari,

Wadawale,

Pathak

et al. 2024

Inorg. Chem.

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The water-soluble trinuclear Pd metallacycles [Pd-(tmeda)(4-Spy)] 3 (X) 3 (tmeda = tetramethylethylenediamine, X = OTf, 2; NO 3 , 3) were synthesized from the ambidentate ligand 4pyridylthiolate (Spy − ) and [Pd(tmeda)X 2 ] in 80 and 70% yield, respectively. Two possible linkage isomers are found in solution (slow interconversion found in the NMR) and in the solid state. Density functional calculations showed that the energy of the isomer with a D 3 -symmetric arrangement of the SPy ligand and all Pd atoms having N∧NPdSN coordination is only 7 kcal/mol lower. When reacting [Pd(tmeda)(NO 3 ) 2 ] with 4,4′-biphenyldithiolate (S 2 bph 2− ), the tetranuclear [{Pd(tmeda)} 4 (μ-S 2 bph) 2 ](NO 3 ) 4 (1) was formed. A new type of undecanuclear Pd cluster was separated as a minor product from an acetone solution of 2 in air. The new complexes represent the first examples of water-soluble Pd metallacycles constructed from a pyridine-thiolate ligand. They show catalytic activity with turnover numbers ranging from 9 to 420 in aqueous Suzuki cross-coupling reactions using phenyl boronic acid and a number of aryl halides. An optimized system gave a TON of 6,900,000 and a TOF of 492,857 h −1 . The catalyst could be reused eight times, and the activity has been attributed to the formation of PdNPs.

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Section: Resultsmentioning

confidence: 99%

Linkage Isomers of Triangular Pd Metallacycles and Catalysis in Aqueous Suzuki Coupling Reaction

Chaudhari,

Wadawale,

Pathak

et al. 2024

Inorg. Chem.

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“…Then, the separated catalyst was rinsed and utilized in another reaction cycle after drying. In 2023, Souza et al 46 designed a sample of a new thioglycolate β-CD derivative joined to palladium (II) chloride (Scheme 9). They used it as an effective supramolecular catalyst for the Suzuki reaction in H 2 O.…”

Section: S C H E M Ementioning

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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“…In addition, the coupling reactions can be performed in the aqueous phase. [18,19] At present, cyclodextrins are mostly modified by nitrogencontaining compounds, [20,21] the electron-rich nitrogen atoms in the structure of molecules possess good coordination ability and can form coordination structures with metal atoms, which are widely used in the field of metal catalysis. Guo et al [22] synthesized an ethylenediamine modified β-CD complexing with Pd(OAc) 2 , and successfully prepared a new catalyst for Suzuki cross-coupling reaction.…”

Section: Introductionmentioning

confidence: 99%

“…The inclusion complex can be formed by the interaction between cyclodextrin and metal ions to fabricate a kind of efficient water‐soluble catalyst with high stability in water [15,16] Moreover, cyclodextrin‐derived ligands can serve as a substitute for phosphines [17] in cross‐coupling reactions because of their low cost, ease of synthesis, and sensitivity to air and moisture. In addition, the coupling reactions can be performed in the aqueous phase [18,19] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Water‐Soluble Pd‐Based Catalyst with a Thymine‐Modified β‐Cyclodextrin Ligand for Suzuki Coupling Reactions

Li,

Jiao

et al. 2023

ChemistrySelect

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Herein, the synthesis and crystal structure identification of thymine‐modified β‐cyclodextrin (mono‐(6‐Thymine‐6‐deoxy)‐β‐CD, Thy‐CD) are reported. The catalyst system (Pd@Thy‐CD) was prepared by using the thymine‐modified β‐cyclodextrin as ligand and palladium acetate (Pd(OAc)2) as palladium source. The as‐obtained Pd@Thy‐CD catalyst was characterized by NMR, IR, SEM, and XPS analysis. The catalyst can efficiently catalyze the aqueous phase Suzuki coupling reaction in situ. Under mild reaction conditions, the catalyst system provides excellent yields for the Suzuki coupling reaction of aryl halides, including with aryl chlorides and aryl boronic acids in water. The major advantages of this technique are the ease of preparation of the palladium catalyst, the aqueous phase coupling reaction, the broad functional group tolerance, and the easy recyclability.

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A new thioglycolic ester β-cyclodextrin/PdCl2 in water: An accessible catalyst for the Suzuki-Miyaura coupling reaction

Cited by 8 publications

References 40 publications

Linkage Isomers of Triangular Pd Metallacycles and Catalysis in Aqueous Suzuki Coupling Reaction

Linkage Isomers of Triangular Pd Metallacycles and Catalysis in Aqueous Suzuki Coupling Reaction

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

Synthesis of a Water‐Soluble Pd‐Based Catalyst with a Thymine‐Modified β‐Cyclodextrin Ligand for Suzuki Coupling Reactions

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