Polyvinylpyridine-Supported Palladium Nanoparticles: An Efficient Catalyst for Suzuki–Miyaura Coupling Reactions

Fusini, Graziano; Rizzo, Fabio; Angelici, Gaetano; Pitzalis, Emanuela; Evangelisti, Claudio; Carpita, Adriano

doi:10.3390/catal10030330

Cited by 22 publications

(15 citation statements)

References 57 publications

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“…The reaction of arylbromides, and iodotoluene was also carried out with 1 (0.004 mol% Pd) to give the corresponding products 6 a – b in 94–99% yields (Entries 12–14). Evangelisti and co‐workers reported palladium nanoparticles supported on poly(4‐vinylpyridine) cross‐linked with divinylbenzene (also known as cross‐linked polyvinylpyridine Pd nanoparticles) for the Suzuki‐Miyaura coupling [15] . In their report, the reaction of arylbromides and ‐iodides was performed with 0.15 mol% Pd in DMA/H 2 O.…”

Section: Resultsmentioning

confidence: 99%

“…Evangelisti and co-workers reported palladium nanoparticles supported on poly(4-vinylpyridine) cross-linked with divinylbenzene (also known as cross-linked polyvinylpyridine Pd nanoparticles) for the Suzuki-Miyaura coupling. [15] In their A heteroaromatic chloride as well as di-and trichlorobenzenes were also suitable substrates for this reaction (Scheme 1). Various functional materials were readily produced under similar conditions in 98-99% yields.…”

Section: Full Papermentioning

confidence: 99%

“…[11] Converting such systems from homogeneous to heterogeneous catalysis is desirable because it would allow these precious transition metal species to be readily recovered and reused. While heterogeneous catalysts including crosslinked polymeric resin-supported palladium catalysts have been reported for Suzuki-Miyaura coupling, [12][13][14][15][16][17][18][19][20][21] heterogeneous catalysts for couplings using CÀ H bonds are still limited. Felpin [22] and MacGlacken [23] have both covered the topic of direct Csp 2 À H arylation using heterogeneous palladium catalysts in their useful reviews.…”

Section: Introductionmentioning

confidence: 99%

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A Convoluted Polyvinylpyridine‐Palladium Catalyst for Suzuki‐Miyaura Coupling and C−H Arylation

et al. 2020

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The development of highly active and reusable supported catalysts for Suzuki-Miyaura coupling and catalytic CÀ H arylation is important for fundamental and applied chemistry, with these reactions being used to produce medical compounds and functional materials. Herein, we found that a mesoporous composite made of a linear poly(4-vinylpyridine) and tetrachloropalladate acted as a dual-mode catalyst for a variety of cross-coupling reactions, with both Pd nanoparticles and a Pd complex catalyst being observed under different conditions. The polyvinylpyridine-palladium composite 1 was readily prepared via the molecular convolution of poly(4-vinylpyridine) and sodium tetrachloropalladate to provide a hardly soluble polymer-metal composite. The Suzuki-Miyaura coupling and the CÀ H arylation of aryl chlorides and bromides with arylboronic acids, thiophenes, furans, benzene, and anisole proceeded in the presence of 0.004 mol% (40 mol ppm) to 1 mol% Pd of 1 to afford the corresponding coupling products in high yields. Furthermore, the catalyst was reused without an appreciable loss of activity. Pharmaceutical compounds and functional materials were synthesized via the coupling reactions. N 2 gas adsorption/desorption analysis indicated that the catalyst had a mesoporous nature, which played a crucial role in the catalysis. In the Suzuki-Miyaura couplings, in situ generated palladium nanoparticles in the polymer matrix were catalytically active, while a polymeric Pd(II) complex was crucial in the CÀ H arylations. These catalytic species were investigated via XAFS, XPS, far-infrared absorption, and Raman spectroscopies, as well as DFT calculations.

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Section: Resultsmentioning

confidence: 99%

Section: Full Papermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Convoluted Polyvinylpyridine‐Palladium Catalyst for Suzuki‐Miyaura Coupling and C−H Arylation

et al. 2020

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“…Pd NPs supported on Smopex ® -111 and Smopex ® -2 obtained through the metal vapor synthesis (MVS) technique. The versatility and fe of this synthetic approach in depositing size-controlled Pd NPs onto a wide r supports, including organic polymers, have been previously established [93][94][95][96][97][98][99][100].…”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

2021

Self Cite

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Supported catalysts are important tools for developing green-economy-based processes. Palladium nanoparticles (NPs) that are immobilized on two fibers developed as metal scavengers (i.e., Smopex®-234 and Smopex®-111, 1% w/w) have been prepared and tested in copper-free cyclocarbonylative Sonogashira reactions. Their catalytic activity has been compared with that of a homogeneous catalyst (i.e., PdCl2(PPh3)2). Pd/Smopex®-234 showed high activity and selectivity in the synthesis of functionalized heterocycles, such as phthalans and isochromans, even when working with a very low amount of palladium (0.2–0.5 mol%). The extension of Pd/Smopex®-234 promoted cyclocarbonylative reactions to propargyl and homopropargyl amides afforded the corresponding isoindoline and dihydrobenzazepine derivatives. A preliminary test on Pd NPs leaching into the solution (1.7 × 10−3 mg) seems to indicate that, at the end of the reaction, almost all of the active metal is present on the fiber surface.

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“…Carbon-carbon bond formation reactions, especially palladium catalyzed ones, are of signi cant reactions in organic chemistry. Among all the palladium catalyzed carbon-carbon bond formation reactions, Heck and Suzuki reactions have attracted interests, due to their high applications in various organic synthesis [1][2][3][4][5][6][7][8] . Regarding the unique advantages of Heck and Suzuki reactions, these reactions are used for the synthesis of several compounds with complex chemical structures [9][10][11][12][13] .…”

Section: Introductionmentioning

confidence: 99%

Pd@Py2PZ@MSN as a Novel and Efficient Catalyst for C-C Bond Formation Reactions

Sayahi

Toosibashi

Bahmaei

et al. 2021

Preprint

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In this paper, a novel catalyst is introduced based on the immobilization of palladium onto dipyrido[3,2-a:2',3'-c]phenazine modified mesoporous silica nanoparticles. Dipyrido[3,2-a:2',3'-c]phenazine (Py2PZ) ligand is synthesized in a simple method from the reaction of 1,10-phenanthroline-5,6-dione and 3,4-diaminobenzoic acid as starting materials. The ligand is used to functionalize mesoporous silica nanoparticles (MSN) and to modify its surface chemistry for immobilization of palladium. The palladium immobilized dipyrido[3,2-a:2',3'-c]phenazine modified mesoporous silica nanoparticles (Pd@Py2PZ@MSN) are synthesized and characterized by several characterization techniques, including TEM, SEM, FTIR, TGA, ICP, XRD, and EDS analysis. After the careful characterization of Pd@Py2PZ@MSN, the activity and efficiency of this catalyst is examined in carbon-carbon bond formation reactions. The results are advantageous in water and the products are obtained in high isolated yields. In addition, the catalyst shows very good reusability and did not show significant loss in activity after 10 sequential runs.

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Polyvinylpyridine-Supported Palladium Nanoparticles: An Efficient Catalyst for Suzuki–Miyaura Coupling Reactions

Cited by 22 publications

References 57 publications

A Convoluted Polyvinylpyridine‐Palladium Catalyst for Suzuki‐Miyaura Coupling and C−H Arylation

A Convoluted Polyvinylpyridine‐Palladium Catalyst for Suzuki‐Miyaura Coupling and C−H Arylation

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

Pd@Py2PZ@MSN as a Novel and Efficient Catalyst for C-C Bond Formation Reactions

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