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.

Palladium stabilized on poly and mono sulfonamide ligands as novel, simple, effective, and recyclable nano catalysts for C–C cross-coupling reactions

2017 ◽  
Vol 95 (10) ◽  
pp. 1073-1080 ◽  
Author(s):  
Ramin Ghorbani-Vaghei ◽  
Narges Sarmast
Keyword(s):  
Catalytic Activity ◽  
Palladium Nanoparticles ◽  
Cross Coupling ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Nano Catalysts ◽  
Reaction Cycles ◽  
Analytical Tools

Poly and mono sulfonamide ligands were successfully used for the stabilization of palladium nanoparticles. The prepared nano catalysts that appeared to be heterogeneous and novel were characterized with various analytical tools. To establish the catalytic activity of the prepared catalysts, they were used in the Suzuki–Miyaura and Sonogashira–Hagihara coupling reactions of aryl halides under low palladium loading conditions. The catalysts showed good stability and could be recovered and reused for seven reaction cycles without significant loss of catalytic activity.

scholarly journals Palladium(II)-catalyzed Suzuki–Miyaura Reactions of Arylboronic Acid with Aryl Halide in the Presence of Aryl-Ferrocenyl-Phosphines

2013 ◽  
Vol 16 (1) ◽  
pp. 79
Author(s):  
A.T. Khabiyev ◽  
B.S. Selenova
Keyword(s):  
Catalytic Activity ◽  
Phenylboronic Acid ◽  
Potassium Phosphate ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Catalyst Precursor ◽  
Coupling Reactions ◽  
Weak Base ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions

<p>This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extreme This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, also for reactions of aryl chlorides by temperature 100 ºC and pressure 1 atm. Sterically demanding and strongly Lewis-basic ferrocene-based phosphines are water- and oxygen-resistant. The Suzuki–Miyaura reaction is also an important reaction in the ground and fine organic synthesis, in the production of drugs and intermediates. To analyze the conversion of halogen aryl compounds the <sup>1</sup>H NMR spectroscopy was used. The advantage of Suzuki–Miyaura reaction in comparison with other cross-coupling reactions (Kumada-, Heck-, Heck-Carbonylation-, Murahashi-, Sonogashira-, Negishi-, Stille-reaktion, etc.) is in the usage of low toxic, water- and oxygen-insensitive thermostable organoboron compounds. As boronic acid was used phenylboronic acid and as weak base – potassium phosphate. Catalyst, precursor and weak base were dissolved in toluene. All reactions were performed under an atmosphere of nitrogen or argon. The catalytic cycle of Suzuki–Miyaura reaction typically includes three main steps: oxidative addition of the haloaromatic to catalytic active palladium (0) species, transmetalation, and reductive elimination of the product under back formation of catalytically active species. All used catalysts showed good activity with aryl bromides and weak activity with aryl chlorides.</p>

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.

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.

Lewis Acid-Promoted Suzuki Reaction using Palladium Chloride Anchored on a Polymer as a Catalyst

2008 ◽  
Vol 61 (8) ◽  
pp. 610 ◽  
Author(s):  
Guozhi Fan ◽  
Hanjun Zhang ◽  
Siqing Cheng ◽  
Zhandong Ren ◽  
Zhijun Hu ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Heterogeneous Catalysts ◽  
Suzuki Reaction ◽  
Cross Coupling ◽  
Palladium Chloride ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Recoverable Catalyst

Palladium chloride anchored on polystyrene modified by 5-amino-1,10-phenanthroline was prepared and used as an efficient recoverable catalyst for Suzuki cross-coupling reactions. The heterogeneous catalysts can be easily separated from the reaction mixture and reused for five cycles without significant Pd leaching and loss of catalytic activity. Rate enhancement in the Suzuki reaction by Lewis acids was also studied.

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.

A cyano-bridged copper(ii)–copper(i) mixed-valence coordination polymer as a source of copper oxide nanoparticles with catalytic activity in C–N, C–O and C–S cross-coupling reactions

2014 ◽  
Vol 38 (9) ◽  
pp. 4267-4274 ◽  
Author(s):  
Manoj Trivedi ◽  
Sanjeev kumar Ujjain ◽  
Raj Kishore Sharma ◽  
Gurmeet Singh ◽  
Abhinav Kumar ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Coordination Polymer ◽  
Copper Oxide ◽  
Mixed Valence ◽  
Cross Coupling ◽  
Copper Oxide Nanoparticles ◽  
Cuo Nanoparticles ◽  
Oxide Nanoparticles ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

A cyano-bridged Cu(ii)–Cu(i) complex was synthesized and transformed into CuO nanoparticles. Their catalytic activity in C–N, C–O, and C–S cross-coupling reactions was explored.

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.

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