Pd(0)-Schiff-base@MCM-41 as high-efficient and reusable catalyst for C–C coupling reactions

Nikoorazm, Mohsen; Ghorbani‐Choghamarani, Arash; Panahi, Atefeh; Tahmasbi, Bahman; Noori, Nourolah

doi:10.1007/s13738-017-1222-x

Cited by 51 publications

(32 citation statements)

References 38 publications

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“…Biochar nanoparticles modified with 3-choloropropyltrimtoxysilane (CPTMS@biochar) were obtained according to a new reported procedure; [42] subsequently CPTMS@biochar (1.0 g) was dispersed in toluene and 1.5 mmol of TBA was added to this mixture. The mixture was stirred at 90°C for 48 h. The solid product (TBA@biochar) was isolated after washing with ethanol and drying at 50°C.…”

Section: Preparation Of Catalystmentioning

confidence: 99%

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Moradi

Hajjami

Valizadeh-kakhki

2019

Applied Organom Chemis

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Biochar is a stable and carbon-rich solid which has a high density of carbonyl, hydroxyl and carboxylic acid functional groups on its surface. In this work, the surface of biochar nanoparticles (BNPs) was modified with 3-choloropropyltrimtoxysilane and further 2-(thiophen-2-yl)-1H-benzo[d]imidazole was anchored on its surface. Then, palladium nanoparticles were fabricated on the surface of the modified BNPs and further the catalytic application was studied as recyclable biocatalyst in carbon-carbon coupling reactions such as Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions. The structure of the catalyst was characterized using scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, X-ray diffraction and atomic absorption spectroscopy. The catalyst can be reused several times without a decrease in its catalytic efficiency.In addition to the several advantages reported, application of biochar as catalyst support for the first time is a major novelty of the present work. 1 H NMR (400 MHz, CDCl 3 ): δ H = 10.09 (s, 1H), 7.99-7.97 (d, J = 8 Hz, 2H), 7.79-7.77 (d, J = 8 Hz, 2H), 7.68-7.66 (d, J = 8 Hz, 2H), 7.53-7.49 (t, J = 8 Hz, 2H), 7.47-7.43 (t, J = 8 Hz, 1H) ppm. 2.5.4 | [1,1′-Biphenyl]-3-carbaldehyde 1 H NMR (400 MHz, CDCl 3 ): δ H = 10.12 (s, 1H), 8.40 (s, 1H), 8.15-8.14 (d, J = 2 Hz, 1H), 7.91-7.87 (td, J = 4 Hz, J = 2 Hz, 1H), 7.68-7.65 (m, 2H), 7.62-7.57 (dd, J = 12 Hz, J = 4 Hz, 1H), 7.53-7.49 (t, J = 8 Hz, 2H), 7.45-7.43 (m, 1H) ppm. 2.5.5 | 3,4-Difluoro-1,1′-biphenyl 1 H NMR (400 MHz, CDCl 3 ): δ H = 7.56-7.54 (d, J = 8 Hz, 2H), 7.49-7.45 (t, J = 8 Hz, 2H), 7.44-7.38 (m, 2H), 7.34-7.31 (m,1H), 7.28-7.21 (m, 1H) ppm. 2.5.6 | Butyl 3-(4-methylphenyl)acrylate 1 H NMR (400 MHz, CDCl 3 ): δ H = 7.70-7.66 (d, J = 16 Hz, 1H), 7.46-7.44 (d, J = 8 Hz, 2H), 7.22-7.20 (d, J = 8 Hz, 2H), 6.44-6.40 (d, J = 16 Hz, 1H), 4.25-4.21 (t, J = 8 Hz, 2H), 2.39 (s, 3H), 1.75-1.68 (quint, J = 8 Hz, 2H), 1.51-1.42 (sextet, J = 8 Hz, 2H), 1.01-0.97 (t, J = 8 Hz, 3H) ppm. | Butyl 3-(4-methoxyphenyl)acrylate

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Section: Preparation Of Catalystmentioning

confidence: 99%

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Moradi

Hajjami

Valizadeh-kakhki

2019

Applied Organom Chemis

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“…Schiff bases are widely used as intermediates in organic synthesis and for industrial purposes. [23,24] Regarding increasing environmental concerns, multicomponent reactions under benign conditions have emerged as highly efficient and atom-economic green processes. [17] During the past few years, there have been many reports of complexes of various Schiff bases with metal ions.…”

Section: Introductionmentioning

confidence: 99%

Immobilized Cu(II) Schiff base complex supported on Fe₃O₄ magnetic nanoparticles: A highly efficient and reusable new catalyst for the synthesis of pyranopyridine derivatives

Azarifar

Mahmoudi‐GomYek

Ghaemi

2018

Applied Organom Chemis

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A new copper(II) Schiff base complex immobilized on silica-coated nanomagnetic Fe 3 O 4 was synthesized from acetylacetonate (acac) and 2aminothiophenol (ATP). The newly synthesized nanocatalyst, Fe 3 O 4 @SiO 2acac-2ATP-Cu(II), was structurally characterized using several analytical techniques. The catalytic activity of the Fe 3 O 4 @SiO 2 -acac-2ATP-Cu(II) nanoparticles was investigated for the synthesis of pyrano[2,3-b]pyridine derivatives from the one-pot three-component reaction of aldehydes, malononitrile and 3-cyano-6-hydroxy-4-methylpyridin-2(1H)-one. A high catalytic performance was exhibited by this nanocatalyst under solvent-free conditions and excellent yields of the products were achieved in reasonably short reaction times. The nanoparticles could be easily separated from the reaction mixture simply by magnetic decantation and reused for several consecutive runs without significant loss of catalytic activity. KEYWORDS acac-2ATP Schiff base-Cu(II) complex, Fe 3 O 4 -immobilized Schiff base copper complex, nanomagnetic Fe 3 O 4 , nanoparticle, pyranopyridine

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“…Al−O vibration in structure of BNPs was observed at 480, 633 and 743 cm −1 . Functionalization of BNPs with organic layers was confirmed by C−H bands vibrations that is appeared at 2859–2927 cm −1 , which these peaks do not observed in FT‐IR spectrum of BNPs.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8] Various solid materials or different nanoparticles were applied as support. For example, carbon nanotubes, [9] polymers, [10,11] silica compounds, [12,13] ionic liquids, [14,15] zeolite, [16] iron oxide, [17,18] graphene oxide, [19][20][21] MCM-41, [22][23][24] and etc. were used as support for the fabrication of homogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

New Complex of Copper on Boehmite Nanoparticles as Highly Efficient and Reusable Nanocatalyst for Synthesis of Sulfides and Ethers

Ghorbani‐Choghamarani

Heidarnezhad

Tahmasbi

2019

ChemistrySelect

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Boehmite is a cubic orthorhombic structure of aluminum oxide hydroxide, which prepared via addition of sodium hydroxide solution to an aluminum nitrate solution at room temperature. In this work, the surface of boehmite nanoparticles (BNPs) modified by 3‐choloropropyltrimtoxysilane (3‐CPTMS), then reacted with N,N,N′,N′‐tetraethyldiethylentriamine (TEDETA). Eventually, CuI immobilized on modified boehmite (CuI‐TEDETA@BNPs). Structure of this catalyst was characterized using FT‐IR, TEM, SEM, EDS, TGA, and AAS techniques. Finally, the catalytic activity of CuI‐TEDETA@BNPs was studied for the synthesis of ethers and sulfides. All ethers and sulfides were obtained in high yields, which reveals the high activity of described catalyst. This catalyst was reused for several times without significant loss of its catalytic efficiency. Recovered catalyst was characterized by SEM and FT‐IR techniques, which shown a good agreement with fresh catalyst. Also, heterogeneity and stability of CuI‐TEDETA@BNPs confirmed by hot filtration test.

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Pd(0)-Schiff-base@MCM-41 as high-efficient and reusable catalyst for C–C coupling reactions

Cited by 51 publications

References 38 publications

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Immobilized Cu(II) Schiff base complex supported on Fe₃O₄ magnetic nanoparticles: A highly efficient and reusable new catalyst for the synthesis of pyranopyridine derivatives

New Complex of Copper on Boehmite Nanoparticles as Highly Efficient and Reusable Nanocatalyst for Synthesis of Sulfides and Ethers

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Pd(0)-Schiff-base@MCM-41 as high-efficient and reusable catalyst for C–C coupling reactions

Cited by 51 publications

References 38 publications

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Immobilized Cu(II) Schiff base complex supported on Fe3O4 magnetic nanoparticles: A highly efficient and reusable new catalyst for the synthesis of pyranopyridine derivatives

New Complex of Copper on Boehmite Nanoparticles as Highly Efficient and Reusable Nanocatalyst for Synthesis of Sulfides and Ethers

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Product

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Immobilized Cu(II) Schiff base complex supported on Fe₃O₄ magnetic nanoparticles: A highly efficient and reusable new catalyst for the synthesis of pyranopyridine derivatives