Heterogenization of Pd(II) complexes as catalysts for the Suzuki-Miyaura reaction

Tovar, Jonathan De; Rataboul, Franck; Djakovitch, Laurent

doi:10.1016/j.apcata.2021.118381

Cited by 19 publications

(10 citation statements)

References 169 publications

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“…MS: m/z (%) = 288 ([M + ], 100), 287 (15), 259 (33), 257 (30), 239 (12), 77 (15), 51 (20), 39 (14) 43 Product 3d was separated as a white solid; yield: 25.9 mg (90%); R f = 0.41 (hexane/CH 2 Cl 2 10:1); mp 111-112 °C. MS: m/z (%) = 288 ([M + ], 100), 259 (34), 257 (27), 239 (11), 77 (13), 51 (13), 39 (9).…”

Section: -(3-fluorophenyl)-2-phenylbenzofuran (3c)mentioning

confidence: 99%

“…In recent years, a wide range of new, selective, efficient catalysts have been developed for C-C coupling reactions of aryl halides with boronic acids (Suzuki coupling), [23][24][25][26][27] or terminal alkynes (Sonogashira coupling) 23,24,[28][29][30] to overcome drawbacks like the use of complicated or toxic ligands, long reaction times, undesirable side reactions, and palladium contamination in the crude product. The catalysts usually afford high conversion and yield under different conditions, in a short reaction time using low palladium/substrate ratio.…”

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confidence: 99%

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Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

et al. 2022

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Suzuki and Sonogashira coupling reactions of 3-iodo-2-phenylbenzofuran, leading to the corresponding 3-aryl- and 3-alkynyl derivatives, respectively, were carried out using a silica supported pyridinium ionic liquid based heterogeneous catalyst. Under optimized reactions conditions, arylboronic acids with either electron withdrawing or -donating substituents as well as terminal alkynes with aromatic or aliphatic groups could be coupled to the benzofuran skeleton efficiently. The application of this catalyst made it possible to carry out the reaction under phosphine-free and, in case of the Sonogashira coupling, under copper-free conditions. The catalyst retained its activity in at least 7 subsequent runs in both types of reactions. Palladium leaching of less than 1% of the original amount used in the catalytic reaction was observed under optimized conditions in most cases. The methodology was applied successfully in the synthesis of nine different 3-aryl- and ten different 3-alkynyl benzofuran derivatives in moderate to high yields.

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Section: -(3-fluorophenyl)-2-phenylbenzofuran (3c)mentioning

confidence: 99%

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confidence: 99%

Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

et al. 2022

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“…Purification of biaryl products was performed by flash chromatography using silica gel. 1 H NMR and 13 C NMR spectra were recorded on a Bruker Biospin AVANCE 300-MHz spectrometer with TMS as an internal reference. Gas chromatography analysis was performed using Shimadzu GC-17 A with dodecane as an internal standard.…”

Section: Materials and Instrumentationmentioning

confidence: 99%

“…Therefore, the development of heterogeneous palladium catalysis has attracted much attention in the last decade. [1][2][3] Among the crosscoupling reactions, the Suzuki-Miyaura reaction is one of the powerful tools to create a carbon-carbon bond from the cross-coupling of aryl boronic acid and aryl halides using a palladium catalyst to synthesize biaryls for industrial uses related to pharmaceuticals, agrochemicals, polymers, and materials. [4,5] Recently, many research groups have demonstrated the use of various kinds of materials as catalyst support for the Suzuki-Miyaura reaction, including organic and inorganic compounds such as metal oxides, [6][7][8][9][10] polymers, [11][12][13][14][15][16][17][18] carbon materials, [19,20] and composite materials.…”

Section: Introductionmentioning

confidence: 99%

Chitosan‐Ethylenediaminetetraacetic acid‐palladium composite for the Suzuki–Miyaura reaction

Khomthawee

Nilada

Homchuen

et al. 2022

Applied Organom Chemis

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Palladium catalyst supported on chitosan‐EDTA composite, CS‐EDTA‐Pd, was prepared by a simple dissolution method. The chitosan and EDTA (1:1.5 by wt.) were dissolved in dilute acetic acid, then formed the beads, which were used to adsorb palladium(II) and finally reduced to palladium(0) by refluxing in ethanol. The as‐prepared CS‐EDTA‐Pd was characterized by Fourier transform infrared (FT‐IR) spectroscopy, scanning electron microscopy (SEM), energy dispersive X‐ray spectrometry (EDX), and X‐ray photoelectron spectroscopy (XPS). Then catalytic activities of the CS‐EDTA‐Pd catalyst were tested in the synthesis of biaryls from aryl halides and phenylboronic acid using the Suzuki–Miyaura cross‐coupling reaction. The results have shown that the CS‐EDTA‐Pd was successfully applied as a catalyst for the Suzuki–Miyaura to couple aryl iodide and aryl bromide substrates under mild reaction conditions using ethanol as solvent and potassium carbonate as a base. The reactions at 80°C for 2 h under a normal atmosphere results in biaryls at good to excellent yields (>90%). This catalyst is inexpensive, simple to prepare, easy to separate from the reaction by filtration, and can be reused for five consecutive runs with a slight loss of product yields.

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“…Since this discovery, the Suzuki-Miyaura cross-coupling reaction has become the preferred method for preparing biaryls by Csp 2 -Csp 2 bond formation, with extensive applications in the synthesis of a wide range of natural products, pharmaceuticals, polymers, and advanced materials [2][3][4][5][6][7][8][9][10]. Initially, tetrakis(triphenylphosphine)palladium(0) was employed as catalyst [11], and since then, much effort has been made to develop more efficient catalytic systems able to accelerate the rate of the crosscoupling and/or substitute brominated derivatives with less reactive compounds such as their chlorinated equivalents or acyl electrophiles [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]. Let us note in particular the use of bisphosphines [27,28], sterically hindered N-heterocyclic carbenes [29][30][31][32][33] or phosphines [34][35][36][37][38][39] and hemilabile biarylphosphines [40][41][42][43] as ligands.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed Suzuki–Miyaura cross-coupling with α-aminophosphonates based on 1,3,4-oxadiazole as ligands

Hkiri¹,

Touil²,

Samarat³

et al. 2022

Comptes Rendus. Chimie

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The synthesis of a palladium complex bearing two diethyl[(5-phenyl-1,3,4-oxadiazol-2ylamino)(4-nitrophenyl)methyl]phosphonates as ligands has demonstrated the ability of this type of α-aminophosphonates to coordinate to the palladium(II) ion via their electronically enriched nitrogen atom of the 1,3,4-oxadiazole ring. The complex was fully characterized by elemental analysis, infrared, NMR and mass spectrometry. A solid-state structure revealed the trans coordination of the two nitrogenated ligands. The presence of a hemilabile P(O)(OEt) 2 moiety in the α-aminophosphonates was exploited into palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl halides. The formation of (N ,O)-chelate intermediates may increase the steric hindrance and the electronic density of the metal, which should favor the oxidative addition and the reductive elimination/product decoordination elementary steps. With our catalytic systems, good activities for the formation of orthodi/trisubstituted biphenyl compounds were observed from aryl bromides using only 0.5 mol% of palladium. Cross-coupling of aryl chlorides required a catalyst loading of 1 mol% to generate orthosubstituted biphenyls.

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Heterogenization of Pd(II) complexes as catalysts for the Suzuki-Miyaura reaction

Cited by 19 publications

References 169 publications

Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

Chitosan‐Ethylenediaminetetraacetic acid‐palladium composite for the Suzuki–Miyaura reaction

Palladium-catalyzed Suzuki–Miyaura cross-coupling with α-aminophosphonates based on 1,3,4-oxadiazole as ligands

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