Suzuki—Miyaura Cross-Coupling Reaction of Aryl Bromides and Chlorides with Phenylboronic Acid under Aerobic Conditions Catalyzed by Palladium Complexes with Thiosemicarbazone Ligands.

ChemInform ◽  
2005 ◽  
Vol 36 (28) ◽  
Author(s):  
Ioannis D. Kostas ◽  
Fotini J. Andreadaki ◽  
Dimitra Kovala-Demertzi ◽  
Christos Prentjas ◽  
Mavroudis A. Demertzis
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Palladium Complexes ◽  
Aerobic Conditions ◽  
Aryl Bromides ◽  
Cross Coupling Reaction

Synthesis, Characterization and Catalytic Utilization of a Ferrocene Diamidodiphosphane

2007 ◽  
Vol 72 (4) ◽  
pp. 453-467 ◽  
Author(s):  
Petr Štěpnička ◽  
Jiří Schulz ◽  
Ivana Císařová ◽  
Karla Fejfarová
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Highly Active ◽  
Aryl Bromides ◽  
Cross Coupling Reaction

Amidation of 1'-(diphenylphosphanyl)ferrocene-1-carboxylic acid (Hdpf) with ethane-1,2-diamine afforded N,N'-ethylenebis[1'-(diphenylphosphanyl)ferrocene-1-carboxamide] (1), which was isolated in free and solvated form, 1·2AcOH. Both 1 and Hdpf were further converted to their respective phosphane sulfides, 2·2AcOH and 3 that were structurally characterized. Testing of the amidophosphane ligands in Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and various aryl halides revealed that catalyst formed in situ from 1 and palladium(II) acetate is highly active in coupling reactions of aryl bromides whilst the corresponding aryl chlorides showed no or only poor conversions. The catalyst based on 2·2AcOH gave markedly lower yields of the coupling products.

scholarly journals A Quantum-Chemical DFT Approach to Elucidation of the Chirality Transfer Mechanism of the Enantioselective Suzuki–Miyaura Cross-Coupling Reaction

2017 ◽  
Vol 2017 ◽  
pp. 1-12 ◽  
Author(s):  
Radomir Jasiński ◽  
Oleg M. Demchuk ◽  
Dmytro Babyuk
Keyword(s):  
Quantum Chemical ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Palladium Complexes ◽  
Initial Reaction ◽  
Chiral Ligand ◽  
Chirality Transfer ◽  
Cross Coupling Reaction ◽  
Enantioselective Reactions ◽  
Selection Of

The DFT calculations of the simplified model of the asymmetric Suzuki–Miyaura coupling reaction were performed at the M062x/LANL2DZ theory level at first. It was found that enantioselective reactions mediated by the palladium complexes of chiral C,P-ligands follow a four-stage mechanism similar to that proposed previously as one of the most credible mechanisms. It should be underlined that the presence of substituents in the substrates and the chiral ligand at ortho positions determines the energies of possible diastereoisomeric transition states and intermediates in initial reaction steps. This suggests that, in practice, a sharp selection of theoretically possible paths of chirality transfer from the catalyst to the product should have a place and, therefore, the absolute configuration of the formed atropisomeric product is defined and can be predicted.

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 

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