scholarly journals 4,6-Bis((E)-2-(4′-N,N-diphenylamino-[1,1′-biphenyl]-4-yl)vinyl)-2-phenylpyrimidine

Molbank ◽  
10.3390/m1278 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1278
Author(s):  
Lacina Diarra ◽  
Françoise Robin-le Guen ◽  
Sylvain Achelle
Keyword(s):  
Bathochromic Shift ◽  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Knoevenagel Reaction ◽  
Polar Solvents ◽  
Cross Coupling Reaction ◽  
Charge Transfer Absorption Band ◽  
Intense Emission ◽  
Emission Quenching ◽  
Electron Donating Groups

In this contribution, we designed a 4,6-distyrylpyrimidine chromophore with diphenylamino electron-donating groups and biphenylenevinylene extended π-conjugated linkers. This compound has been synthesized in two steps from 4,6-dimethyl-2-phenylpyrimidine by a double Knoevenagel reaction with 4-bromobenzaldehyde followed by a double Suzuki–Miyaura cross coupling reaction with 4-(N,N-diphenylamino)phenylboronic acid. This compound exhibits intense emission in moderately polar solvents as well as in solid state. This compound is characterized by an intense emission solvatochromism with emission ranging from blue in non polar n-heptane to orange in dichloromethane. This chromophore is also sensible to the presence of acid with a bathochromic shift of the charge transfer absorption band and emission quenching.

scholarly journals Flow Process Development and Optimization of A Suzuki-Miyaura Cross Coupling Reaction using Response Surface Methodology

2020 ◽  
Vol 15 (3) ◽  
pp. 604-616
Author(s):  
Girish Basavaraju ◽  
Ravishankar Rajanna
Keyword(s):  
Response Surface Methodology ◽  
Response Surface ◽  
Flow Reactor ◽  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Flow Process ◽  
Cross Coupling Reaction ◽  
Custom Made ◽  
Good Agreement

A custom-made tubular flow reactor was utilized to develop a mathematical model and optimize the Suzuki-Miyaura cross coupling reaction. In this study, the experimentation was designed and executed through the statistical design of experiments (DoE) approach via response surface methodology. The effect of molar ratios of phenylboronic acid (1) and 4-bromophenol (2), temperature, the catalyst tetrakis(triphenylphosphine)palladium, and equivalence of aqueous tripotassium phosphate was studied in detail. The flow reactor profile was in good agreement with batch conditions and significant improvements to the overall reaction time and selectivity towards desired [1-1-biphenyl]-4-ol (3) was achieved. The Suzuki coupling reaction in batch condition would take on an average of 4 to 6 hours to complete, which was effectively accomplished in 60 to 70 minutes in this tubular reactor setup and could be operated continuously. The reaction model is in good agreement with the reaction conditions. Copyright © 2020 BCREC Group. All rights reserved 

Suzuki-Miyaura Cross-Coupling Towards 4-Amino Biphenyl Intermediates

2019 ◽  
Author(s):  
Tomasz Jastrząbek ◽  
Artur Ulikowski ◽  
Rafał Lisiak
Keyword(s):  
Chemical Industry ◽  
Short Communication ◽  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Groups ◽  
Aryl Chlorides ◽  
Cross Coupling Reaction ◽  
Direct Cross

The preparation of biphenyl derivatives bearing amino groups via direct cross-coupling reaction is being widely explored due to its importance for many branches of the chemical industry. One of the necessary components for such a transformation are halogenated arenes. In order to make the process more economical, we focus on inexpensive and easily available aryl chlorides which usually are not considered reagents of choice for catalytic couplings. In the following short communication, we report the results of the coupling of relatively unreactive chloroaniline with a fluorinated phenylboronic acid leading to the corresponding aminobiphenyl.<br>

scholarly journals Morphology Control and Metallization of Porous Polymers Synthesized by Michael Addition Reactions of a Multi-Functional Acrylamide with a Diamine

Materials ◽  
2021 ◽  
Vol 14 (4) ◽  
pp. 800
Author(s):  
Naofumi Naga ◽  
Minako Ito ◽  
Aya Mezaki ◽  
Hao-Chun Tang ◽  
Tso-Fu Mark Chang ◽  
...  
Keyword(s):  
Phase Separation ◽  
Michael Addition ◽  
Phenylboronic Acid ◽  
Monomer Concentration ◽  
Coupling Reaction ◽  
Porous Polymer ◽  
Porous Polymers ◽  
Cross Coupling Reaction ◽  
Internal Phase ◽  
Polymerization Induced Phase Separation

Porous polymers have been synthesized by an aza-Michael addition reaction of a multi-functional acrylamide, N,N′,N″,N‴-tetraacryloyltriethylenetetramine (AM4), and hexamethylene diamine (HDA) in H2O without catalyst. Reaction conditions, such as monomer concentration and reaction temperature, affected the morphology of the resulting porous structures. Connected spheres, co-continuous monolithic structures and/or isolated holes were observed on the surface of the porous polymers. These structures were formed by polymerization-induced phase separation via spinodal decomposition or highly internal phase separation. The obtained porous polymers were soft and flexible and not breakable by compression. The porous polymers adsorbed various solvents. An AM4-HDA porous polymer could be plated by Ni using an electroless plating process via catalyzation by palladium (II) acetylacetonate following reduction of Ni ions in a plating solution. The intermediate Pd-catalyzed porous polymer promoted the Suzuki-Miyaura cross coupling reaction of 4-bromoanisole and phenylboronic acid.

scholarly journals Mono- and Bimetallic Nanoparticles Stabilized by an Aromatic Polymeric Network for a Suzuki Cross-Coupling Reaction

Nanomaterials ◽  
2021 ◽  
Vol 12 (1) ◽  
pp. 94
Author(s):  
Linda Zh. Nikoshvili ◽  
Kristina N. Shkerina ◽  
Alexey V. Bykov ◽  
Alexander I. Sidorov ◽  
Alexander L. Vasiliev ◽  
...  
Keyword(s):  
Bimetallic Nanoparticles ◽  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
High Catalytic Activity ◽  
Zno Nps ◽  
Catalyst Recycling ◽  
Catalyst Composition ◽  
Water Solvent ◽  
Cross Coupling Reaction

This work addresses the Suzuki cross-coupling between 4-bromoanisole (BrAn) and phenylboronic acid (PBA) in an environmentally benign ethanol–water solvent catalysed by mono- (Pd) and bimetallic (PdAu, PdCu, PdZn) nanoparticles (NPs) stabilised within hyper-cross-linked polystyrene (HPS) bearing tertiary amino groups. Small Pd NPs of about 2 nm in diameters were formed and stabilized by HPS independently in the presence of other metals. High catalytic activity and complete conversion of BrAn was attained at low Pd loading. Introduction of Zn to the catalyst composition resulted in the formation of Pd/Zn/ZnO NPs, which demonstrated nearly double activity as compared to Pd/HPS. Bimetallic core-shell PdAu/HPS samples were 3-fold more active as compared to Pd/HPS. Both Pd/HPS and PdAu/HPS samples revealed promising stability confirmed by catalyst recycling in repeated reaction runs.

scholarly journals Pd(II) Complexes with Nitrogen-oxygen Donor Ligands: Synthesis, Characterization and Catalytic Activity for Suzuki-Miyaura Cross-coupling Reaction

2014 ◽  
Vol 31 (1) ◽  
pp. 15
Author(s):  
M.T Amalina ◽  
B Hadariah ◽  
K Karimah ◽  
W.I.W Nazihah
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Donor Ligands ◽  
Azomethine Nitrogen ◽  
Catalyst Loading ◽  
Cross Coupling Reaction ◽  
Oxygen Donor ◽  
Counter Ions ◽  
Square Planar

Inexpensive bidentate Schiff base ligands (O1, O3) and their Pd(II) complexes (OPd1, OPd3) were successfully synthesized and characterized using CHN elemental analysis, FTIR, 1H and 13C NMR, melting point determination, molar conductivity and magnetic moment. It revealed that these Schiff bases behaved as bidentate ligands in their complexes. The spectral data indicated that the ligands co-ordinated through the phenolic oxygen and the azomethine nitrogen atoms. Magnetic momentdata suggested the existence of square planar Pd(II) complexes, while non-electrolytic behaviour indicated the absence of counter ions in chloroform. The Pd(II) complexes showed good catalytic activities for Suzuki-Miyaura cross-coupling reaction between iodobenzene with phenylboronic acid at 1.0 mmol% catalyst loading.

scholarly journals POSSIBILITY OF PECTIN APPLICATION FOR THE DEVELOPMENT OF SUZUKI REACTION CATALYSTS

2020 ◽  
pp. 26-30
Author(s):  
Полина Михайловна Рассказова ◽  
Линда Жановна Никошвили
Keyword(s):  
Catalytic Properties ◽  
Ambient Pressure ◽  
Phenylboronic Acid ◽  
Suzuki Reaction ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Water Mixture ◽  
Batch Mode ◽  
Modified Alumina ◽  
Cross Coupling Reaction

Работа посвящена синтезу Pd-содержащих катализаторов на основе пектина и исследованию их каталитических свойств в реакции кросс-сочетания Сузуки. Была синтезирована серия катализаторов на основе пектина при варьировании способа осаждения металла. Катализаторы были протестированы в реакции кросс-сочетания между 4-броманизолом и фенилбороновой кислотой в периодическом режиме при атмосферном давлении в смеси этанола и воды с использованием NaCO в качестве основания. Показано, что наибольшей активностью обладает катализатор Pd/(пектин-AlO), в ходе приготовления которого палладий наносился на модифицированный пектином оксид алюминия (конверсия 4-броманизола за 3 ч составила 90%). This work is devoted to the synthesis of Pd-containing catalysts based on pectin and study of their catalytic properties in the Suzuki cross-coupling reaction. A series of catalysts based on pectin was synthesized by varying the method of metal deposition. The catalysts were tested in cross-coupling reaction between 4-bromanisole and phenylboronic acid in a batch mode at ambient pressure in ethanol-water mixture using NaCO as a base. It was shown that the catalyst Pd/(pectin-AlO), which was synthesized via deposition of palladium on pectin-modified alumina, revealed highest activity (conversion of 4-bromanisole for 3 h of reaction reached 90%).

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