Effect on orthometallation of NHC palladium complexes toward the catalytic activity studies in Suzuki coupling reaction

2017 ◽  
Vol 46 (47) ◽  
pp. 16394-16398 ◽  
Author(s):  
Ming-Tsz Chen ◽  
Zing-Lun Kao
Keyword(s):  
Catalytic Activity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Palladium Complexes ◽  
Coupling Reactions ◽  
Suzuki Coupling Reaction ◽  
Cross Coupling Reactions

Herein, we report an approach to improve catalytic activity for cross-coupling reactions.

An efficient and new protocol for phosphine-free Suzuki coupling reaction using palladium-encapsulated and air-stable MIDA boronates in an aqueous medium

RSC Advances ◽  
2014 ◽  
Vol 4 (53) ◽  
pp. 28148-28155 ◽  
Author(s):  
Joaquim Fernando Mendes da Silva ◽  
Andres Felipe Yepes Perez ◽  
Natália Pinto de Almeida
Keyword(s):  
Aqueous Medium ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Coupling Reactions ◽  
Suzuki Coupling Reaction ◽  
Cross Coupling Reactions ◽  
Water Alcohol

A simple methodology for Suzuki–Miyaura cross-coupling reactions using microencapsulated palladium and (het)aryl MIDA boronates in water–alcohol under phosphine-free conditions was developed.

Routes to some 3,6-disubstituted phthalonitriles and examples of phthalocyanines derived therefrom: An overview

2013 ◽  
Vol 17 (08n09) ◽  
pp. 649-664 ◽  
Author(s):  
Martin J. Heeney ◽  
Shaya A. Al-Raqa ◽  
Aurélien Auger ◽  
Paul M. Burnham ◽  
Andrew N. Cammidge ◽  
...  
Keyword(s):  
Metal Ion ◽  
Near Infrared ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Central Metal ◽  
Coupling Reactions ◽  
Negishi Coupling ◽  
Suzuki Coupling Reaction ◽  
Cross Coupling Reactions

The paper reviews a selection of synthetic pathways that provide access to 3,6-disubstituted phthalonitriles, precursors for the synthesis of 1,4,8,11,15,18,22,25-octasubstituted phthalocyanine derivatives. Early routes using Diels–Alder reactions for the synthesis of 3,6-dialkyl, 3,6-dialkoxymethyl, 3,6-dialkenyl and 3,6-diphenylphthalonitriles are appraised. However, the emphasis of the review focuses on the scope and applications of 2,3-dicyanohydroquinone as a starting material for obtaining 3,6-disubstituted phthalonitriles. The earliest example of the use of 2,3-dicyanohydroquinone concerned its O -alkylation to afford 3,6-dialkoxyphthalonitriles. These are immediate precursors to near-infrared absorbing phthalocyanine derivatives. Triflation of 2,3-dicyanohydroquinone extends the scope of the compound for phthalocyanine synthesis; the bis-triflate derivative is susceptible to S N Ar reactions and readily reacts with thiols to provide 3,6-bis(alkylsulfanyl) and 3,6-bis(arylsulfanyl)phthalonitriles. 3,6-Bis(phenylselenyl)phthalonitrile has also been obtained recently from the same precursor. Phthalocyanine derivatives obtained from them typically show a strongly bathochromically shifted Q-band absorption that is particularly sensitive to the central metal ion. The bis-triflate of 2,3-dicyanohydroquinone is also an ideal precursor for participation in cross-coupling reactions. Examples from the University of East Anglia group and elsewhere are presented which show the application of the nickel-catalyzed Negishi coupling reaction using alkylzinc halide derivatives. Yields of 3,6-dialkylphthalonitriles and 3,6-bis(substituted alkyl)phthalonitriles range from ca. 40 to 70%. Direct comparison for one example shows that the yield from the Negishi coupling method is higher than that using the Suzuki coupling protocol. Examples of the preparation of 3,6-diarylphthalonitriles from 2,3-dicyanohydroquinone bis-triflate using the Suzuki coupling reaction are reported with yields of the order of 65–70%. The review also includes a further application of 2,3-dicyanohydroquinone as a precursor to both monobromo and dibromo derivatives of 3,6-dibutoxyphthalonitrile. These compounds provide opportunities for cross-coupling at the brominated sites to provide more complex derivatives with the potential to serve as precursors of highly substituted phthalocyanine derivatives.

scholarly journals Palladium-bearing intermetallic electride as an efficient and stable catalyst for Suzuki cross-coupling reactions

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Tian-Nan Ye ◽  
Yangfan Lu ◽  
Zewen Xiao ◽  
Jiang Li ◽  
Takuya Nakao ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Density Functional ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Suzuki Coupling Reaction ◽  
Cross Coupling Reactions ◽  
Catalytic Stability ◽  
High Carrier

AbstractSuzuki cross-coupling reactions catalyzed by palladium are powerful tools for the synthesis of functional organic compounds. Excellent catalytic activity and stability require negatively charged Pd species and the avoidance of metal leaching or clustering in a heterogeneous system. Here we report a Pd-based electride material, Y3Pd2, in which active Pd atoms are incorporated in a lattice together with Y. As evidenced from detailed characterization and density functional theory (DFT) calculations, Y3Pd2 realizes negatively charged Pd species, a low work function and a high carrier density, which are expected to be beneficial for the efficient Suzuki coupling reaction of activated aryl halides with various coupling partners under mild conditions. The catalytic activity of Y3Pd2 is ten times higher than that of pure Pd and the activation energy is lower by nearly 35%. The Y3Pd2 intermetallic electride catalyst also exhibited extremely good catalytic stability during long-term coupling 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.

Construction of light-harvesting system for enhanced catalytic performance of Pd nanoframes toward Suzuki coupling reaction

2017 ◽  
Vol 5 (21) ◽  
pp. 10150-10153 ◽  
Author(s):  
Lini Yang ◽  
Qi Zhan ◽  
Zhenni Wang ◽  
Qiang Chen ◽  
Jing Tong ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Light Harvesting ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Catalytic Performance ◽  
Coupling Reactions ◽  
Suzuki Coupling Reaction

Au octahedra have been encapsulated into Pd nanoframes to further enhance the catalytic activity of Pd nanoframes toward Suzuki coupling reactions.

Biosynthesis of poly(ethylene glycol)-supported palladium nanoparticles using Colocasia esculenta leaf extract and their catalytic activity for Suzuki–Miyaura cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (89) ◽  
pp. 72453-72457 ◽  
Author(s):  
Raju Kumar Borah ◽  
Hirak Jyoti Saikia ◽  
Abhijit Mahanta ◽  
Vijay Kumar Das ◽  
Utpal Bora ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Poly Ethylene Glycol ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Supported Palladium ◽  
Poly Ethylene ◽  
Supported Pd

A green and efficient method for the synthesis of PEG supported Pd-NPs has been developed using aqueous extract of C. esculanta leaf. The prepared NPs show excellent catalytic activity for Suzuki–Miyaura cross-coupling reaction at room temperature.

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 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.

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>

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