[60]Fullerene-Based Pd(0) Complexes of Phosphorus Ylides as Efficient Nanocatalyst for Homo- and Heterogeneous Mizoroki–Heck Coupling Reactions

Sabounchei, Seyyed Javad; Hashemi, Ali; Hosseinzadeh, Marjan; Salehzadeh, Sadegh; Maleki, Farahnaz

doi:10.1007/s10562-017-2147-9

Cited by 11 publications

(5 citation statements)

References 51 publications

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“…Mono‐ and bidentate Pd(0)‐C 60 complexes prepared by reaction of α‐keto phosphorous ylides have been prepared by Sabounchei and co‐workers . These complexes have been prepared by reaction of C 60 with Pd(dba) 2 in toluene followed by addition of the phosphorous ylide at rt.…”

Section: Palladium‐supported On C60mentioning

confidence: 99%

“…[a] Pd catalyst according to mg. Sabounchei and co-workers. [159] These complexes have been prepared by reaction of C 60 with Pd(dba) 2 in toluene followed by addition of the phosphorous ylide at rt. The most active catalyst in the Heck reaction was the palladacycle complex working with aryl chlorides and styrene at rt (Scheme 38).…”

Section: Palladium-supported On C 60mentioning

confidence: 99%

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Carbon‐Derived Supports for Palladium Nanoparticles as Catalysts for Carbon‐Carbon Bonds Formation

Naghshbandi

Nájera

2019

ChemCatChem

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The review considers the variety allotropes of carbon to be used as supports for palladium and investigation of the resulting catalysts for carbon‐carbon forming reactions with focus on the catalyst recovery and effect of the solvent, base and catalyst loading in the efficiency of reactions. Specially, carbon nanotubes, C60 and graphene allowed the covalent functionalization with different ligands for palladium facilitating a lower leaching. Magnetic iron nanoparticles can be easily covered by charcoal, graphene oxide and carbon quantum dots facilitating the recovery of the supported catalyst. These heterogeneous catalysts are able to activate even aryl chlorides in cross‐coupling reactions such as Suzuki‐Miyaura, Mizoroki‐Heck and Sonogashira‐Hagihara in organic but also in aqueous media. All these features favoured the applicability of the materials for industrial processes.

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Section: Palladium‐supported On C60mentioning

confidence: 99%

Section: Palladium-supported On C 60mentioning

confidence: 99%

Carbon‐Derived Supports for Palladium Nanoparticles as Catalysts for Carbon‐Carbon Bonds Formation

Naghshbandi

Nájera

2019

ChemCatChem

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“…[12] Sabounchei et al found that palladium(0)- [60] fullerene complexes as effective heterogeneous catalysts for Heck coupling reactions of aryl chlorides. [13,14] Incorporating a magnetic base in designing photocatalyst was found quite effective in quick separation and re-usability and with this strategy, magnetic Fe 3 O 4 -Polyamidoamine supported cobalt nanoparticle (magnetic-Fe 3 O 4 NP/PAMAM-Co NP) [15] and two catalysts viz the magnetic melamine-cyanuric chloride functionalized cobalt nanoparticle supported chitosan (Melamine-cyanuric/Co-MNPs/ CS) catalyst and cyanuric chloride-bromohydroxybenzaldehyde functionalized cobalt nanoparticle supported chitosan (cyanuric-bromohydroxybenzaldehyde/Co-MNPs/CS) catalysts have been illustrated as successful protocols for the coupling of aryl halides with alkene affording good to excellent yields. [16] The magnetically separable catalysts containing Pd-nanoparticles were quite effective for CÀ C coupling, tolerating a variety of olefins, giving a negligible loss of costly Pd which otherwise got leached in the product.…”

Section: Introductionmentioning

confidence: 99%

Visible Light Mediated Heck Coupling of Inactivated Aryl Fluoride/Chloride Over a Sulfonic Acid Functionalized, Melamine‐based Metal‐free Porphyrin Photocatalyst

Bhuse

Bhagat

2022

ChemistrySelect

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We report the synthesis of a new, sulfonic acid functionalized, melamine‐based metal‐free porphyrin photocatalyst (MBMFPc) for the C−C coupling of the most unreactive aryl halides with alkenes under visible light irradiation. The ionic liquid‐based photocatalyst was characterized using various analytical techniques Proton Nuclear Magnetic Resonance (1HNMR) Spectroscopy, Carbon Nuclear Magnetic Resonance (13CNMR) Spectroscopy, Fourier Transformed Infrared Spectroscopy (FT‐IR), Energy‐dispersive X‐ray Spectroscopy (EDAX), Scanning Electron Microscope (SEM), Brunauer‐Emmett‐Teller (B.E.T) and Ultraviolet‐Visible Spectroscopy (UV‐Vis). The MBMFPc photocatalyst with noticeable Hammett acidity (0.56) and optimal bandgap of 1.44 eV was found to as an effective catalyst in the Mizoroki‐Heck coupling of inactivated aryl fluoride/chloride using 5 W LED in a homemade photoreactor under ambient conditions. The protocol comprising metal‐free green photocatalyst tolerated a variety of aliphatic/aromatic alkenes bearing different substituents afforded good to excellent yields. The role of photogenerated excitons was confirmed by scavenger studies with K2S2O8 and EDTA. The leaching test, stability, and reusability of MBMFPc photocatalyst evidenced as a perfect heterogeneous photocatalyst and afford appreciable yield (80 %) after 5 cycles. A plausible mechanism for photocatalytic C−C coupling has been proposed and described. A metal‐free acid‐functionalized ionic liquid‐based MBMFPc photocatalyst with appreciable TON (4,51,948) and TOF (22,597 h−1) could gain significant attraction as a green catalyst in the pharmaceutical industries for the synthesis of intermediates by C−C coupling using commercial aryl chlorides.

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“…Additionally, Pd (II) complexes bearing phosphine groups have been extensively applied as efficient catalysts in some cross‐coupling reactions, specifically, the Mizoroki‐Heck reaction. The Mizoroki‐Heck reaction, has emerged as the most important and reliable method for construction of functionalized olefins, and it can be catalyzed with the Pd (II) complexes of such phosphorus ylides . Palladium complexes ( 1 and 2 ) were employed as homogeneous catalysts in C‐C coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

“…The Mizoroki-Heck reaction, has emerged as the most important and reliable method for construction of functionalized olefins, and it can be catalyzed with the Pd (II) complexes of such phosphorus ylides. [18,19] Palladium complexes (1 and 2) were employed as homogeneous catalysts in C-C coupling reactions. There are many controlling factors such as base, solvent, temperature, time, catalyst (mol%), etc.…”

Section: Introductionmentioning

confidence: 99%

Spectral and crystallography studies of new palladacycle complexes with P,C‐ and C,C‐donor ligands; Application of (OAL16) to optimizing the yield of Mizoroki‐Heck reaction

Sabounchei

Badpa

Hashemi

et al. 2019

Applied Organom Chemis

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The new symmetrical diphosphonium salt [Ph2P(CH2)2PPh2(CH2C(O)C6H4Br)2] Br2 (S) was synthesized in the reaction of 1,2‐bis (diphenylphosphino) ethane (dppe) and related ketone. Further treatment with NEt3 gave the symmetrical α‐keto stabilized diphosphine ylide [Ph2P(CH2)2PPh2(CHC(O)C6H4Br)2] (Y1). The unsymmetrical α‐keto stabilized diphosphine ylide [Ph2P(CH2)2PPh2(CHC(O)C6H4Br)] (Y2) was synthesized in the reaction of diphosphine in 1:1 ratio with 2.3′‐dibromoacetophenone, then treatment with NEt3. The reaction of dibromo (1,5‐cyclooctadiene)palladium (II), [PdBr2(COD)] with this ligand (Y1) in equimolar ratio gave the new C,C‐chelated [PdBr2(Ph2P(CH2)2PPh2(C(H)C(O)C6H4Br)2)] (1) and with unsymmetrical phosphorus ylide [Ph2P(CH2)2PPh2C(H)C(O)C6H4Br] (Y2) gave the new P, C‐chelated palladacycle complex [PdBr2(Ph2P(CH2)2PPh2C(H)C(O)Br)] (2). These compounds were characterized successfully by FT‐IR, NMR (1H, 13C and 31P) spectroscopic methods and the crystal structure of Y1 and 2 were elucidated by single crystal X‐ray diffraction. The results indicated that the complex 1 was C, C‐chelated whereas complex 2 was P, C‐chelated. These air/moisture stable complexes were employed as efficient catalysts for the Mizoroki‐Heck cross‐coupling reaction of several aryl chlorides, and the Taguchi method was used to optimize the yield of Mizoroki‐Heck coupling. The optimum condition was found to be as followed: base; K2CO3, solvent; DMF and loading of catalyst; 0.005 mmol.

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[60]Fullerene-Based Pd(0) Complexes of Phosphorus Ylides as Efficient Nanocatalyst for Homo- and Heterogeneous Mizoroki–Heck Coupling Reactions

Cited by 11 publications

References 51 publications

Carbon‐Derived Supports for Palladium Nanoparticles as Catalysts for Carbon‐Carbon Bonds Formation

Carbon‐Derived Supports for Palladium Nanoparticles as Catalysts for Carbon‐Carbon Bonds Formation

Visible Light Mediated Heck Coupling of Inactivated Aryl Fluoride/Chloride Over a Sulfonic Acid Functionalized, Melamine‐based Metal‐free Porphyrin Photocatalyst

Spectral and crystallography studies of new palladacycle complexes with P,C‐ and C,C‐donor ligands; Application of (OAL16) to optimizing the yield of Mizoroki‐Heck reaction

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