scholarly journals A magnetically retrievable air and moisture stable gold and palladium nanocatalyst for efficient C−C coupling reactions

2020 ◽  
Vol 7 (9) ◽  
pp. 200916
Author(s):  
Chatura Goonesinghe ◽  
Mohamed Shaik ◽  
Rivi Ratnaweera ◽  
K. M. Nalin De Silva ◽  
Rohini M. De Silva
Keyword(s):  
Phenylboronic Acid ◽  
Cross Coupling ◽  
Significant Loss ◽  
Metal Species ◽  
Prolonged Storage ◽  
Coupling Reactions ◽  
Highly Active ◽  
Minimal Loss ◽  
Low Concentrations ◽  
Selective Catalysis

In this study, we report the synthesis of a highly stable, magnetically retrievable gold and palladium nanocatalyst (AuPd@AMNPs), highly active in Suzuki cross-coupling and related homocoupling reactions. The active catalytic component in this system is palladium, which can only be stabilized in the presence of gold nanoparticles. There is no significant loss of activity even after prolonged storage exposed air and moisture. The versatile nature AuPd@AMNPs is demonstrated through the selective catalysis of the homocoupling of phenylboronic acid under low concentrations of O 2 and the oxidation of phenylboronic acid to phenol under high O 2 concentrations. AuPd@AMNPs also demonstrated Ullmann-type homocoupling of 4-iodotolene with excellent yields. The magnetically retrieved catalyst could be re-used up to six times in Suzuki–Miyaura cross-coupling with consistently high activity and with a minimal loss of the noble metal species. Through these reactions we show that the gold-stabilized AuPd@AMNPs can be used as stable and recyclable palladium reservoir for multiple palladium-catalysed reactions.

Pyridinyl functionalized MCM-48 supported highly active heterogeneous palladium catalyst for cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (25) ◽  
pp. 19630-19637 ◽  
Author(s):  
Shaheen M. Sarkar ◽  
Md. Lutfor Rahman ◽  
Mashitah Mohd Yusoff
Keyword(s):  
Palladium Catalyst ◽  
Cross Coupling ◽  
Significant Loss ◽  
Pd Catalyst ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Supported Pd ◽  
Heterogeneous Palladium Catalyst

Pyridinyl functionalized MCM-48-supported Pd-catalyst efficiently (0.013–0.025 mol%) promoted Heck, Suzuki and Sonogashira cross-coupling reactions. Moreover, the catalyst was reused five times without significant loss of its activity.

scholarly journals QuadraPure-Supported Palladium Nanocatalysts for Microwave-Promoted Suzuki Cross-Coupling Reaction under Aerobic Condition

2014 ◽  
Vol 2014 ◽  
pp. 1-7 ◽  
Author(s):  
Kin Hong Liew ◽  
Poh Lee Loh ◽  
Joon Ching Juan ◽  
Mohd Ambar Yarmo ◽  
Rahimi M. Yusop
Keyword(s):  
Catalytic Activity ◽  
Mechanical Stability ◽  
Physical Adsorption ◽  
Phenylboronic Acid ◽  
Reduction Process ◽  
Cross Coupling ◽  
Aerobic Condition ◽  
Significant Loss ◽  
Coupling Reactions ◽  
Palladium Nanocatalysts

Cross-linked resin-captured palladium (XL-QPPd) was readily prepared by simple physical adsorption onto the high loading QuadraPure macroporous resin and a subsequent reduction process. To enhance the mechanical stability, entrapped palladium nanocatalysts were cross-linked with succinyl chloride. Both transmission electron microscopy images and X-ray diffraction analysis revealed that the palladium nanoparticles were well dispersed with diameters ranging in 4–10 nm. The catalyst performed good catalytic activity in microwave-promoted Suzuki cross-coupling reactions in water under aerobic condition with mild condition by using various aryl halides and phenylboronic acid. In addition, the catalyst showed an excellent recyclability without significant loss of catalytic activity.

Synthesis, Characterization and Catalytic Utilization of a Ferrocene Diamidodiphosphane

2007 ◽  
Vol 72 (4) ◽  
pp. 453-467 ◽  
Author(s):  
Petr Štěpnička ◽  
Jiří Schulz ◽  
Ivana Císařová ◽  
Karla Fejfarová
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Highly Active ◽  
Aryl Bromides ◽  
Cross Coupling Reaction

Amidation of 1'-(diphenylphosphanyl)ferrocene-1-carboxylic acid (Hdpf) with ethane-1,2-diamine afforded N,N'-ethylenebis[1'-(diphenylphosphanyl)ferrocene-1-carboxamide] (1), which was isolated in free and solvated form, 1·2AcOH. Both 1 and Hdpf were further converted to their respective phosphane sulfides, 2·2AcOH and 3 that were structurally characterized. Testing of the amidophosphane ligands in Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and various aryl halides revealed that catalyst formed in situ from 1 and palladium(II) acetate is highly active in coupling reactions of aryl bromides whilst the corresponding aryl chlorides showed no or only poor conversions. The catalyst based on 2·2AcOH gave markedly lower yields of the coupling products.

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

2020 ◽  
Vol 17 (11) ◽  
pp. 857-863
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Phenylboronic Acid ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Salen Complex ◽  
Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

Cytostatic 6-Arylpurine Nucleosides II. Synthesis of Sugar-Modified Derivatives: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-Deoxy-β-D-ribofuranosyl)- and 9-(2,3-Dihydroxypropyl)-6-phenylpurines

2000 ◽  
Vol 65 (11) ◽  
pp. 1683-1697 ◽  
Author(s):  
Michal Hocek ◽  
Antonín Holý ◽  
Ivan Votruba ◽  
Hana Dvořáková
Keyword(s):  
Cross Coupling ◽  
Cytostatic Activity ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Phenylboronic Acids

9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-(4-substituted phenyl)purines, 9-(5-deoxy-β-D-ribofuranosyl)-6-(4-substituted phenyl)purines and 9-(2,3-dihydroxypropyl)-6-(4-substituted phenyl)purines were prepared by the Suzuki-Miyaura cross-coupling reactions of the corresponding protected 9-substituted 6-chloropurines with substituted phenylboronic acids followed by MeONa mediated deprotection. In contrast to the highly active 6-phenylpurine ribonucleosides, the title compounds did not show any considerable cytostatic activity.

Highly Active Heterogeneous PdCl2 /MOF Catalyst for Suzuki-Miyaura Cross-Coupling Reactions of Aryl Chloride

2020 ◽  
Vol 646 (15) ◽  
pp. 1336-1341 ◽  
Author(s):  
Xue-Fang Gong ◽  
Ling-Yan Zhang ◽  
Hui-Xin Zhang ◽  
Yu-Meng Cui ◽  
Fen-Chun Jin ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Aryl Chloride ◽  
Cross Coupling Reactions ◽  
Highly Active

Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble
Keyword(s):  
Phenylboronic Acid ◽  
Palladium Catalysis ◽  
Suzuki Reaction ◽  
Tetrabutylammonium Bromide ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.Key words: palladium, cross-coupling, regioselectivity, quinolines, boronic acids.

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