scholarly journals Facile Synthesis and Characterization of Palladium@Carbon Catalyst for the Suzuki-Miyaura and Mizoroki-Heck Coupling Reactions

2021 ◽  
Vol 11 (11) ◽  
pp. 4822
Author(s):  
Hamed M. Alshammari ◽  
Obaid F. Aldosari ◽  
Mohammad Hayal Alotaibi ◽  
Raja L. Alotaibi ◽  
Mosaed S. Alhumaimess ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Activated Carbon ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
High Catalytic Activity ◽  
Coupling Reactions ◽  
Heck Coupling ◽  
Efficient Catalyst ◽  
X Ray ◽  
Suzuki Reactions

Palladium-based carbon catalysts (Pd/C) can be potentially applied as an efficient catalyst for Suzuki–Miyaura and Mizoroki–Heck coupling reactions. Herein, a variety of catalysts of palladium on activated carbon were prepared by varying the content of ‘Pd’ via an in situ reduction method, using hydrogen as a reducing agent. The as-prepared catalysts (0.5 wt % Pd/C, 1 wt % Pd/C, 2 wt % Pd/C and 3 wt % Pd/C) were characterized using X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and Brunauer–Emmett–Teller (BET) analyses. The catalysts were tested as a coupling catalyst for Suzuki–Miyaura coupling reactions involving aryl halides and phenyl boronic acid. The optimization of the catalyst by varying the palladium content on the activated carbon yielded Pd/C catalysts with very high catalytic activity for Suzuki reactions of aryl halides and a Mizoroki–Heck cross-coupling reaction of 4-bromoanisol and acrylic acid in an aqueous medium. A high ‘Pd’ content and uniform ‘Pd’ impregnation significantly affected the activity of the catalysts. The catalytic activity of 3% Pd/C was found to make it a more efficient catalyst when compared with the other synthesized Pd/C catalysts. Furthermore, the catalyst reusability was also tested for Suzuki reactions by repeatedly performing the same reaction using the recovered catalyst. The 3% Pd/C catalyst displayed better reusability even after several reactions.

Pd/Indanone-Based Ligands: An Efficient Catalyst System for Ullmann­-Type, Suzuki–Miyaura, and Mizoroki–Heck Cross-Coupling Reactions with Aryl Tosylates and Aryl Halides

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4372-4382 ◽  
Author(s):  
Mohammed Waheed ◽  
Naseem Ahmed
Keyword(s):  
Catalytic Activity ◽  
Cross Coupling ◽  
Catalyst System ◽  
Aryl Halides ◽  
Maximum Efficiency ◽  
High Catalytic Activity ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Cross Coupling Reactions ◽  
Aryl Tosylates

2-Hydroxyindan-1-ones have been efficiently synthesized and successfully applied as ligands in Pd-catalyzed Ullmann type, Suzuki–Miyaura, and Mizoroki–Heck cross-coupling reactions with aryl tosylates and aryl halides. The ligands are air- and moisture-stable and have shown high catalytic activity with Pd(OAc)2 in these cross-coupling reactions. The system tolerates a variety of functional groups in the product and can be re-used at least three times with maximum efficiency.

scholarly journals One-Pot Synthesized Pd@N-Doped Graphene: An Efficient Catalyst for Suzuki–Miyaura Couplings

Catalysts ◽  
2019 ◽  
Vol 9 (5) ◽  
pp. 469 ◽  
Author(s):  
Mufsir Kuniyil ◽  
J. V. Shanmukha Kumar ◽  
Syed Farooq Adil ◽  
Mohammed Rafi Shaik ◽  
Mujeeb Khan ◽  
...  
Keyword(s):  
Graphene Oxide ◽  
Catalytic Activity ◽  
Photoelectron Spectroscopy ◽  
Coupling Reaction ◽  
Ammonium Hydroxide ◽  
Coupling Reactions ◽  
One Pot ◽  
Efficient Catalyst ◽  
X Ray ◽  
Doped Graphene

Nitrogen-doped graphene (NDG)-palladium (Pd)-based nanocatalysts (NDG@Pd) can be potentially applied as an efficient catalyst for the preparation of biaryls in a Suzuki–Miyaura coupling reaction. Herein, we report the one-pot facile synthesis of an NDG@Pd nanocatalyst, wherein the nanocatalyst was prepared by the simultaneous reduction of graphene oxide (GRO) and PdCl2 in the presence of hydrazine hydrate as a reducing agent, while ammonium hydroxide was used as a source of “N’’ on the surface of graphene. The as-synthesized NDG@Pd nanocatalyst, consisting of smaller-sized, spherical-shaped palladium nanoparticles (Pd-NPs) on the surface of NDG, was characterized by several spectroscopic and microscopic techniques, including high-resolution transmission electron microscopy (HRTEM), X-ray diffraction (XRD), ultraviolet–visible spectroscopy (UV-Vis), Fourier-transform infrared spectroscopy (FT-IR), X-ray photoelectron spectroscopy (XPS), and Brunauer–Emmett–Teller (BET). The nanocatalyst displayed outstanding catalytic activity in the Suzuki–Miyaura cross-coupling reactions of phenyl halides with phenyl boronic acids under facile conditions in water. The catalytic activity of NDG@Pd was found to be a more efficient catalyst when compared to pristine highly reduced graphene oxide (HRG) based Pd nanocatalyst (HRG@Pd). Furthermore, the reusability of the catalyst was also tested by repeatedly performing the same reaction using the recovered catalyst. The N-doped catalyst displayed excellent reusability even after several reactions.

A highly efficient catalyst for Suzuki–Miyaura coupling reaction of benzyl chloride under mild conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (69) ◽  
pp. 36437-36443 ◽  
Author(s):  
Zhenhong Guan ◽  
Buyi Li ◽  
Guoliang Hai ◽  
Xinjia Yang ◽  
Tao Li ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Benzyl Chloride ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Microporous Polymers ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Cross Coupling Reactions

Microporous polymers with built-in triphenylphosphine palladium exhibit highly efficient catalytic activity for cross-coupling reactions of benzyl chloride under mild conditions.

scholarly journals Synthesis and characterization of a new bis-NHC palladium complex and its catalytic activity in the Mizoroki–Heck reaction

2020 ◽  
Vol 44 (11-12) ◽  
pp. 684-688
Author(s):  
Can Feng ◽  
Cheng-xin Liu ◽  
Yu-fang Wang ◽  
Jin Cui ◽  
Ming-jie Zhang
Keyword(s):  
Palladium Complex ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Heck Coupling ◽  
X Ray ◽  
X Ray Crystallography ◽  
H Nmr ◽  
Excellent Stability ◽  
C Nmr

A new bis- N-heterocyclic carbene palladium complex, (C13H9N2F2)2PdCl2, is synthesized by a three-step reaction and characterized by 1H NMR and 13C NMR spectroscopy as well as by X-ray crystallography. This new bis- N-heterocyclic carbene palladium complex has excellent stability and is capable of efficiently catalyzing the Mizoroki–Heck coupling reaction of aryl halides with acrylates.

scholarly journals Microwave Assisted Novel Efficient Pd-free Catalyst for Suzuki C-C Coupling Reaction

2018 ◽  
Author(s):  
Ghalia Alzhrani ◽  
Nesreen Ahmed ◽  
Elham Aazam ◽  
Mohamed Mokhtar
Keyword(s):  
Photoelectron Spectroscopy ◽  
Inductively Coupled Plasma ◽  
Coupling Reaction ◽  
Optical Emission ◽  
Nickel Catalysts ◽  
Aryl Halides ◽  
Precipitation Method ◽  
Coupling Reactions ◽  
Nickel Ions ◽  
X Ray

Suzuki cross-coupling reaction has developed one of the furthermost effectual approaches for the synthesis of biaryls or substituted aromatic moieties from aryl halides and arylboronic acids with a palladium-catalyst in the past two era’s. Herein, Pd-free layered double hydroxide containing nickel catalysts were prepared by co-precipitation method under ultrasonic irradiation and N2 atmosphere with different molar ratios of Ni: Mg: Al and coded as (1NiLDHs-Dr), (1.5NiLDHs-Dr) and (2NiLDHs-Dr). A series of reduced catalysts under 5%H2/N2 at different temperatures were coded as 1NiLDHs-R200, 1.5NiLDHs-R200 and 2NiLDHs-R200. As-synthesized 2NiLDHs-Dr was the superlative catalyst when coupling different aryl halides with different boronic acids derivatives. Deep investigation of all catalysts was done using different techniques such as inductively coupled plasma optical emission spectroscopy (ICP-OES), x-ray photoelectron spectroscopy (XPS), powder x-ray diffraction (XRD), thermogravimetric analyses (TGA), Fourier transfer infrared (FTIR), scanning electron microscope (SEM) connected with energy dispersive x-ray (EDX) and N2-physisorption at -196 ℃. The results attained verified that ɑ-Ni(OH)2 was fashioned for 2NiLDHs-Dr catalyst and the enclosure of nickel ions in the cationic sheet of layered structure were responsible for the fascinating catalytic efficacy rather than the basic nature of material. The Ni-containing LDHs catalysts encourage forthcoming studies in Pd-free catalyzed C-C coupling reactions.

A facile synthesis of a solvent-dispersible magnetically recoverable Pd0 catalyst for the C–C coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (61) ◽  
pp. 56028-56034 ◽  
Author(s):  
Li Wu ◽  
Bin Yuan ◽  
Mengmeng Liu ◽  
Hongfei Huo ◽  
Yu Long ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
High Yield ◽  
Heck Coupling ◽  
Facile Synthesis ◽  
Efficient Catalyst ◽  
Cross Coupling Reaction

A Pd0/Fe3O4-DA/DMG catalyst exhibited excellent catalytic activity toward the Suzuki, Heck and Kumada cross coupling reaction with a high yield. It is an especially efficient catalyst for Suzuki and Heck coupling in water.

scholarly journals Synthesis, Photophysical Properties and Catalytic Activity of Ƙ3-SCS Pincer Palladium (II) Complex of N,N'-Di-Tert-Butylbenzene-1,3-Dicarbothioamide Supported by DFT Analysis

2021 ◽  
Author(s):  
Debasish Das ◽  
S. Kannan ◽  
Mukesh Kumar ◽  
Biswajit Sadhu ◽  
Liladhar B. Kumbhare
Keyword(s):  
Catalytic Activity ◽  
Uv Light ◽  
Photophysical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Vis Spectroscopy

The title complex [PdCl(L)] (1), is obtained from the reaction of SCS pincer ligand HL (where, HL = N,N'-di-tert-butylbenzene-1,3-dicarbothioamide) with lithium tetrachloropalladate (II) in methanol. The compound 1 is characterized by elemental analysis, FTIR, 1H, and 13C-NMR spectroscopy, UV-Vis spectroscopy, powder X-ray diffraction and X-ray crystallographic techniques. At room temperature, 1 emits luminescence light of wavelength 460 nm in the solid state upon excitation by UV light of wavelength 280 nm. The average emission lifetime indicates that, both the ligand and complex emission is fluorescence in nature and involves mainly ligand centers π-π* deexcitation. It also shows good catalytic activity towards Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions of aryl bromides with tert-butyl acrylate and p-tolylboronic acid respectively. For both type of reactions, more than 99% conversion of the substrates is found to occur for electronically activated p-nitro bromobenzene using 1 mol % of 1. Further, modern DFT calculations are performed to decipher the mechanistic insight on the preferable pathways of the Mizoroki-Heck cross-coupling reaction. Stepwise free energy of reactions for various probable reaction pathways suggest that the catalytic route has profound preference for Pd(0)-Pd(II) over Pd(II)-Pd(IV) pathway.<br>

scholarly journals Microwave Assisted Novel Efficient Pd-free Catalyst for Suzuki C-C Coupling Reaction

2019 ◽  
Author(s):  
Ghalia Alzhrani ◽  
Nesreen Ahmed ◽  
Elham Aazam ◽  
Mohamed Mokhtar ◽  
Tamer Saleh
Keyword(s):  
Photoelectron Spectroscopy ◽  
Inductively Coupled Plasma ◽  
Coupling Reaction ◽  
Optical Emission ◽  
Nickel Catalysts ◽  
Aryl Halides ◽  
Precipitation Method ◽  
Coupling Reactions ◽  
Nickel Ions ◽  
X Ray

Suzuki cross-coupling reaction has developed one of the furthermost effectual approaches for the synthesis of biaryls or substituted aromatic moieties from aryl halides and arylboronic acids with a palladium-catalyst in the past two era&rsquo;s. Herein, Pd-free layered double hydroxide containing nickel catalysts were prepared by co-precipitation method under ultrasonic irradiation and N2 atmosphere with different molar ratios of Ni: Mg: Al and coded as (1NiLDHs-Dr), (1.5NiLDHs-Dr) and (2NiLDHs-Dr). A series of reduced catalysts under 5%H2/N2 at different temperatures were coded as 1NiLDHs-R200, 1.5NiLDHs-R200 and 2NiLDHs-R200. As-synthesized 2NiLDHs-Dr was the superlative catalyst when coupling different aryl halides with different boronic acids derivatives. Deep investigation of all catalysts was done using different techniques such as inductively coupled plasma optical emission spectroscopy (ICP-OES), x-ray photoelectron spectroscopy (XPS), powder x-ray diffraction (XRD), thermogravimetric analyses (TGA), Fourier transfer infrared (FTIR), scanning electron microscope (SEM) connected with energy dispersive x-ray (EDX) and N2-physisorption at -196 ℃. The results attained verified that ɑ-Ni(OH)2 was fashioned for 2NiLDHs-Dr catalyst and the enclosure of nickel ions in the cationic sheet of layered structure were responsible for the fascinating catalytic efficacy rather than the basic nature of material. The Ni-containing LDHs catalysts encourage forthcoming studies in Pd-free catalyzed C-C coupling reactions.

scholarly journals Improved Suzuki–Miyaura reaction conversion efficiency using magnetic nanoparticles and inductive heating

2022 ◽  
Author(s):  
Alejandro Villacampa ◽  
Luis Duque ◽  
Olga Juanes ◽  
Francisco Javier Palomares ◽  
Pilar Herrasti ◽  
...  
Keyword(s):  
Magnetic Field ◽  
Catalytic Activity ◽  
Magnetic Nanoparticles ◽  
Size Structure ◽  
Local Heating ◽  
Inductive Heating ◽  
High Catalytic Activity ◽  
Coupling Reactions ◽  
X Ray ◽  
Substrate Conversion

AbstractThe use of magnetic nanoparticles in C–C coupling reactions enables the facile recovery of the catalyst under environmentally friendly conditions. Herein, the synthesis of Pd/Fe@Fe3O4 nanoparticles by the reduction of Pd2+ and oxidation of Fe on the surface of preformed Fe@Fe3O4 is reported. The nanoparticles were characterized using a variety of analytical techniques (transmission electron microscopy, Mössbauer spectroscopy, X-ray photoelectron spectroscopy, and X-ray diffraction) to determine their size, structure, and chemical composition. The catalytic efficiency of these nanoparticles in classical Suzuki–Miyaura coupling reactions was investigated. The nanoparticles achieved high catalytic activity with the application of local heating by an alternating magnetic field. An investigation was conducted at identical temperatures to compare global heating with the application of an external magnetic field; magnetic heating demonstrated excellent substrate conversion in lesser time and at a lower temperature. The catalyst could also be recycled and reused three times, with ~ 30% decrease in the substrate conversion, which is most likely due to the agglomeration of the Pd nanoparticles or poisoning of the Pd catalyst. This approach, which takes advantage of the catalytic activity and magnetic susceptibility of magnetic nanoparticles, can be applied to several organic transformations to improve their efficiency. Graphical abstract

scholarly journals Modified ultradispersed diamonds based catalytic systems in cross-coupling reactions

2021 ◽  
Vol 57 (1) ◽  
pp. 7-14
Author(s):  
A. A. Lugovski ◽  
G. A. Gusakov ◽  
M. P. Samtsov ◽  
V. A. Parhomenko ◽  
S. V. Adamchyk
Keyword(s):  
Catalytic Activity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Model Systems ◽  
High Catalytic Activity ◽  
Coupling Reactions ◽  
Catalytic Systems ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Metallic Palladium

Methods for preparation of nanocomposites of modified detonation nanodiamonds (DND) with metallic palladium have been developed and their catalytic activity in the Suzuki-Miyaura cross-coupling reaction in various reaction media has been studied. Methods for the regeneration of palladium-containing nanocomposites from the reaction mixture have been developed. The high catalytic activity of nanocomposites is confirmed by kinetic analysis based on the results of chromatographic analysis of the reaction mixture and is comparable to the literature data about similar catalytic systems. Regenerated nanocomposites showed the retention of catalytic activity for 3 consecutive cross-coupling cycles on model systems.

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