scholarly journals A robust polyfunctional Pd(II)-based magnetic amphiphilic nanocatalyst for the Suzuki–Miyaura coupling reaction

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Hamideh Aghahosseini ◽  
Mohammad Reza Saadati ◽  
Seyed Jamal Tabatabaei Rezaei ◽  
Ali Ramazani ◽  
Narges Asadi ◽  
...  
Keyword(s):  
Magnetic Nanoparticles ◽  
Nitrogen Atom ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Monomethyl Ether ◽  
Separation Procedure ◽  
Artificial Enzyme ◽  
High Turnover ◽  
Protein Mimics ◽  
Artificial Metalloenzyme

AbstractHerein, a robust Pd(II)-based polyfunctional magnetic amphiphilic artificial metalloenzyme was prepared by anchoring a Pd(2,2′-dipyridylamine)Cl2 bearing hydrophilic monomethyl ether poly(ethylene glycol) (mPEG) chains on the surface of amino-functionalized silica-coated magnetic nanoparticles. The 2,2′-dipyridylamine (dpa) has shown excellent complexation properties for Pd(II) and it could be easily anchored onto functionalized magnetic support by the bridging nitrogen atom. Moreover, the bridging nitrogen atom at the proximity of Pd(II) catalytic center could play an important role in dynamic suppramolecular interactions with substrates. The leaching, air and moisture resistant [Pd(dpa)Cl2] complex endow the dynamic and robust structure to the designed artificial enzyme. Moreover, the water dispersibility of designed artificial metalloenzyme raised from mPEG chains and the magnetic nanoparticles core which could function as protein mimics endow it other necessary characters of artificial enzymes. The prepared artificial metalloenzyme displayed remarkable activity in Suzuki–Miyaura cross-coupling reaction employing low-palladium loading under mild conditions, with the exceptionally high turnover frequency, clean reaction profile, easy work-up procedure, good to excellent products yields and short reaction times. The designed air- and moisture-stable artificial metalloenzyme could recycle more than fifteen times with easy separation procedure in aqueous solution under aerobic conditions without any noticeable loss in activity.

scholarly journals The Eschenmoser coupling reaction under continuous-flow conditions

2011 ◽  
Vol 7 ◽  
pp. 1164-1172 ◽  
Author(s):  
Sukhdeep Singh ◽  
J Michael Köhler ◽  
Andreas Schober ◽  
G Alexander Groß
Keyword(s):  
Continuous Flow ◽  
Elevated Temperatures ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Flow Chemistry ◽  
Flow Conditions ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

The Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Eschenmoser coupling needs prolonged reaction times and elevated temperatures to deliver valuable yields. We have used a flow chemistry system to promote the Eschenmoser coupling under enhanced reaction conditions in order to convert the demanding precursors such as S-alkylated secondary thioamides and thiolactames in an efficient way. Under pressurized reaction conditions at about 220 °C, the desired Eschenmoser coupling products were obtained within 70 s residence time. The reaction kinetics was investigated and 15 examples of different building block combinations are given.

scholarly journals Pd(CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-coupling Reaction of Bromoaryl Carboxylic Acids in Water

Catalysts ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 86 ◽  
Author(s):  
Xiaogang Li ◽  
Wenbin Zhang ◽  
Leiqing Fu ◽  
Mengping Guo
Keyword(s):  
Catalytic System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Catalytic Performance ◽  
High Turnover ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Pipecolinic Acid ◽  
Excellent Catalytic Performance

In this study, a convenient and highly efficient catalytic system for the Suzuki-Miyaura coupling reaction was investigated under mild conditions. A combination of Pd(CH3CN)2Cl2 and pipecolinic acid showed excellent catalytic performance and afforded high turnover numbers; turnover numbers were up to 4.9 × 105 for the coupling reaction of 4-bromobenzoic acid and tetraphenylboron sodium. The catalytic system was also effective for the indexes of 4-bromobenzoic acid, and high turnover numbers were obtained.

Ru3(CO)12-Catalyzed Coupling Reaction of sp3C−H Bonds Adjacent to a Nitrogen Atom in Alkylamines with Alkenes

2001 ◽  
Vol 123 (44) ◽  
pp. 10935-10941 ◽  
Author(s):  
Naoto Chatani ◽  
Taku Asaumi ◽  
Shuhei Yorimitsu ◽  
Tsutomu Ikeda ◽  
Fumitoshi Kakiuchi ◽  
...  
Keyword(s):  
Nitrogen Atom ◽  
Coupling Reaction

Gold immobilized onto poly(ionic liquid) functionalized magnetic nanoparticles: a robust magnetically recoverable catalyst for the synthesis of propargylamine in water

RSC Advances ◽  
2015 ◽  
Vol 5 (43) ◽  
pp. 34502-34510 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Seyed Ebrahim Ayati ◽  
Seyed Hassan Hosseini ◽  
Ali Pourjavadi
Keyword(s):  
Ionic Liquid ◽  
Magnetic Nanoparticles ◽  
Coupling Reaction ◽  
Highly Active ◽  
Recoverable Catalyst ◽  
Functionalized Magnetic Nanoparticles ◽  
Magnetically Recoverable Catalyst ◽  
Poly Ionic Liquid ◽  
Supported Gold ◽  
Green Conditions

Supported gold(iii) on poly(ionic liquid) coated on magnetic nanoparticles produced a highly active, stable, recoverable and high loading for the synthesis of propargylamines (A3 coupling reaction) under green conditions.

Continuous Synthesis of Inorganic Magnetic Nanocomposites by Laser Pyrolysis for Biomedical Applications

2006 ◽  
Vol 962 ◽  
Author(s):  
Sabino Veintemillas ◽  
Brigitte Bouchet-Fabre ◽  
Maria Puerto Morales ◽  
Yann Leconte ◽  
R Costo ◽  
...  
Keyword(s):  
Magnetic Nanoparticles ◽  
Magnetic Measurements ◽  
Reaction Times ◽  
Organic Matrix ◽  
Silica Coating ◽  
Step Method ◽  
Magnetic Composites ◽  
Laser Pyrolysis ◽  
Pyrolysis Method ◽  
Inorganic Matrix

ABSTRACTNanocomposite particles made from encapsulation of magnetic nanoparticles in an inorganic matrix have a real interest in biomedicine due to their high resistance against biodegradation compared with nanoparticles encapsulated in an organic matrix and little work has been published concerning such materials. In this work we use the laser pyrolysis method for the preparation of magnetic composites of Fe-based nanoparticles dispersed in silica and carbon. The precursor is an aerosol of a precursor which can be easily used in a safe way. Important advantages of the laser pyrolysis method are the reproducibility, simplicity (one step method) and continuity which allows producing significant amounts of nanoparticles. The short reaction times (ms) involved in the nucleation of the powders insure the nanometric particle size of both the magnetic component and the inorganic matrix.This paper is focused on the synthesis and characterization of the Fe@SiO2 and Fe@C nanopowders generated by laser pyrolysis of ferrocene diluted in toluene and carried to the reaction zone in aerosol form. The silica coating was formed by the addition of tetraethoxysilane (TEOS) to the reactant. The samples were characterized by X-ray diffraction (XRD), infrared spectroscopy (IR), transmission electron microscopy (TEM), specific surface area determination (BET) and magnetic measurements. In the case of Fe@SiO2 the process generates rather homogeneous iron/magnetite particles smaller than 10 nm in diameter surrounded by a SiO2 coating of about 20 nm. In the case Fe@C the process generate iron based magnetic nanoparticles of complex composition smaller than 11 nm surrounded by a graphitic carbon layer of 50 nm. Stable aqueous dispersions at physiological pH were produced for both systems by means of strong oxidation in aqueous solutions, which is a very encouraging result for application in the field of living tissues.

scholarly journals Studies on Pd/NiFe2O4 catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls

2011 ◽  
Vol 7 ◽  
pp. 310-319 ◽  
Author(s):  
Sanjay R Borhade ◽  
Suresh Babsaheb Waghmode
Keyword(s):  
Active Catalyst ◽  
Suzuki Reaction ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Solvent Mixture ◽  
Phase Synthesis ◽  
Suzuki Coupling Reaction ◽  
Arylboronic Acids ◽  
Highly Active ◽  
Ligand Free

Palladium supported on nickel ferrite (Pd/NiF2O4) was found to be a highly active catalyst for the Suzuki coupling reaction between various aryl halides and arylboronic acids. The reaction gave excellent yields (70–98%) under ligand free conditions in a 1:1 DMF/H2O solvent mixture, in short reaction times (10–60 min). The catalyst could be recovered easily by applying an external magnetic field. The polyaryls were similarly synthesized.

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