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 novel 4-aminoantipyrine-Pd(II) complex catalyzes Suzuki–Miyaura cross-coupling reactions of aryl halides

2014 ◽  
Vol 10 ◽  
pp. 2821-2826 ◽  
Author(s):  
Claudia Araceli Contreras-Celedón ◽  
Darío Mendoza-Rayo ◽  
José A Rincón-Medina ◽  
Luis Chacón-García
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Cross Coupling Reaction ◽  
Phenylboronic Acids

A simple and efficient catalytic system based on a Pd complex of 4-aminoantipyrine, 4-AAP–Pd(II), was found to be highly active for Suzuki–Miyaura cross-coupling of aryl iodides and bromides with phenylboronic acids under mild reaction conditions. Good to excellent product yields from the cross-coupling reaction can be achieved when the reaction is carried out in ethanol, in the open air, using low loading of 4-AAP–Pd(II) as a precatalyst, and in the presence of aqueous K2CO3 as the base. A variety of functional groups are tolerated.

scholarly journals Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Cytotoxic Activities ◽  
Coupling Reactions ◽  
Component System ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.

scholarly journals Recent Progress in the Cross-Coupling Reaction Using Triorgano­silyl-Type Reagents

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1873-1884 ◽  
Author(s):  
Yasunori Minami ◽  
Tamejiro Hiyama ◽  
Takeshi Komiyama
Keyword(s):  
Recent Progress ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Organosilicon Compounds ◽  
Aryl Bromides ◽  
Cross Coupling Reaction ◽  
The Cross ◽  
Silicon Based ◽  
Coupling Polymerization

The silicon-based cross-coupling reaction has attracted much attention over recent decades because there are many advantages in using organosilicon compounds. However, the use of reagents with a triorganosilyl group as a key function remains to be established. This account summarizes our recent progress in cross-coupling chemistry with such silyl reagents.1 Introduction2 Preparation of HOMSi Reagents from Aryl Bromides and Disilanes3 HOMSi Reagents from Heteroaromatics and Hydrosilanes4 Cross-Coupling Polymerization with HOMSi Reagents5 Cross-Coupling with Aryl(triethyl)silanes6 Amination of Aryl Halides with N-TMS-Amines7 Conclusion and Perspective

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>

A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

2014 ◽  
Vol 12 (22) ◽  
pp. 3735-3743 ◽  
Author(s):  
Sebastián O. Simonetti ◽  
Enrique L. Larghi ◽  
Teodoro S. Kaufman
Keyword(s):  
Double Bond ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
One Pot ◽  
Cross Coupling Reaction

A one-pot approach towards β-methylstyrenes is reported. The transformation involves a Stille cross-coupling reaction of aryl halides with allyltributylstannane, followed by an in situ Pd-catalyzed double bond conjugative migration.

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