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 Pd-Fe3O4/RGO: a Highly Active and Magnetically Recyclable Catalyst for Suzuki Cross Coupling Reaction using a Microfluidic Flow Reactor

2019 ◽  
Vol 14 (3) ◽  
pp. 478
Author(s):  
Hany A. Elazab ◽  
Ali R. Siamaki ◽  
B. Frank Gupton ◽  
M. Samy El-Shall
Keyword(s):  
Flow Reactor ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Cross Coupling Reaction ◽  
Continuous Reaction ◽  
Applied Catalysis

There are several crucial issues that need to be addressed in the field of applied catalysis. These issues are not only related to harmful environmental impact but also include process safety concerns, mass and heat transfer limitations, selectivity, high pressure, optimizing reaction conditions, scale-up issues, reproducibility, process reliability, and catalyst deactivation and recovery. Many of these issues could be solved by adopting the concept of micro-reaction technology and flow chemistry in the applied catalysis field. A microwave assisted reduction technique has been used to prepare well dispersed, highly active Pd/Fe3O4 nanoparticles supported on reduced graphene oxide nanosheets (Pd-Fe3O4/RGO), which act as a unique catalyst for Suzuki cross coupling reactions due to the uniform dispersion of palladium nanoparticles throughout the surface of the magnetite - RGO support. The Pd-Fe3O4/RGO nanoparticles have been shown to exhibit extremely high catalytic activity for Suzuki cross coupling reactions under both batch and continuous reaction conditions. This paper reported a reliable method for Suzuki cross-coupling reaction of 4-bromobenzaldehyde using magnetically recyclable Pd/Fe3O4 nanoparticles supported on RGO nanosheets in a microfluidic-based high throughput flow reactor. Organic synthesis can be performed under high pressure and temperature by using a stainless steel micro tubular flow reactor under continuous flow reaction conditions. Optimizing the reaction conditions was performed via changing several parameters including temperature, pressure, and flow rate. Generally, a scalable flow technique by optimizing the reaction parameters under high-temperature and continuous reaction conditions could be successfully developed.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

scholarly journals 2-(3-Cyanopropyldimethylsilyl)ethyl as a Polar Sulfur Protecting Group

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4153-4164
Author(s):  
Linda M. Bannwart ◽  
Pascal S. Rieder ◽  
Marcel Mayor
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Thiol Group ◽  
Organosulfur Compounds ◽  
Coupling Reactions ◽  
Protecting Group ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
The Stability

Organosulfur compounds are ubiquitous in synthetic chemistry, biology and materials chemistry. The reactivity of free sulfhydryls requires their masking in many synthetic strategies. To facilitate the isolation of protected thiols by chromatography, we propose 2-(3-cyanopropyldimethylsilyl)ethyl as a polar protecting group analogue of 2-(trimethylsilyl)ethyl. The masked thiophenol is obtained in two synthetically complementing ways. Either an existing thiophenol is protected, or the protected thiol group is introduced by a cross-coupling reaction. In both cases the required reagents are readily available from inexpensive starting materials. Thiol protection and thiol introduction both tolerate a large variety of functional groups and substitution patterns, and the protected thiophenols are stable toward a broad range of reaction conditions. The stability of the protected derivatives in cross-coupling reactions and the mild reaction conditions for the release of the protecting group further emphasizes the potential of the methodology.

scholarly journals POxAP Precatalysts and the Negishi Cross-Coupling Reaction

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 51-59
Author(s):  
Shuang-Qi Tang ◽  
Martine Schmitt ◽  
Frédéric Bihel
Keyword(s):  
Functional Groups ◽  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Catalytic Activities ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Wide Range ◽  
Organozinc Reagents

Recently developed for the Fukuyama reaction, post-oxidative addition precatalysts (POxAPs) are also very efficient in catalyzing Negishi cross-coupling reactions between organohalides and organozinc reagents. Using very low catalyst loadings, POxAPs show similar catalytic activities to those of classical precatalysts such as XPhos Pd G4 or PEPPSI-IPr, with turnover numbers of up to 93,000. POxAPs are easily prepared, are stable to air and moisture, tolerate a wide range of functional groups in the Negishi cross-coupling reaction and contribute advantageously to the arsenal of organic chemists in terms of Pd precatalysts.

Palladium-Catalyzed Copper-Promoted Hiyama-Type Carbon–­Carbon Cross-Coupling Reactions of Dihetaryl Disulfides as ­Electrophiles

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 330-335 ◽  
Author(s):  
Zheng-Jun Quan ◽  
Xi-Cun Wang ◽  
Ming-Xia Liu ◽  
Hai-Peng Gong
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
High Reactivity ◽  
Attractive Alternative ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Dihetaryl disulfides were used as electrophiles in a palladium-catalyzed carbon–carbon cross-coupling reaction with arylsilanes to ­realize a Hiyama-type reaction. This unique transformation shows high reactivity, excellent functional-group tolerance, and mild reaction conditions, making it an attractive alternative to conventional cross-coupling approaches for carbon−carbon bond construction.

A 2-((4-Arylpiperazin-1-yl)methyl)phenol ligated Pd(ii) complex: an efficient, versatile catalyst for Suzuki–Miyaura cross-coupling reactions

2016 ◽  
Vol 40 (9) ◽  
pp. 7596-7603 ◽  
Author(s):  
Srinivas Keesara ◽  
Saiprathima Parvathaneni
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction

N,N,O-Tridentate palladium(ii) complex 4a was found to be an efficient catalyst for the Suzuki cross-coupling reaction of aryl halides (iodo-, bromo- and chloro-), which afforded cross-coupling products in good to excellent yields.

scholarly journals C(acyl)–C(sp2) and C(sp2)–C(sp2) Suzuki–Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes

RSC Advances ◽  
2021 ◽  
Vol 11 (60) ◽  
pp. 37684-37699
Author(s):  
Sinem Çakır ◽  
Serdar Batıkan Kavukcu ◽  
Hande Karabıyık ◽  
Senthil Rethinam ◽  
Hayati Türkmen
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Palladium Complexes ◽  
Coupling Reactions ◽  
Acyl Chlorides ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Phenylboronic Acids

Nitrile-functionalized Pd(ii) complexes have evaluated for the Suzuki–Miyaura cross-coupling reactions. The highest TON value was reached for the acylative Suzuki–Miyaura cross-coupling reaction of acyl chlorides with phenylboronic acids.

Nickel-catalyzed cross-coupling of aldehydes with aryl halides via hydrazone intermediates

2018 ◽  
Vol 54 (14) ◽  
pp. 1750-1753 ◽  
Author(s):  
Jianting Tang ◽  
Leiyang Lv ◽  
Xi-Jie Dai ◽  
Chen-Chen Li ◽  
Lu Li ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Classical Cross ◽  
Opening Up

A novel nickel-catalyzed cross-coupling reaction between aldehydes and aryl halides via hydrazone intermediates has been developed. It merges the Wolff–Kishner reduction and classical cross-coupling reactions, thus opening up new routes in designing chemical synthesis.

Highly active mesoionic chalcogenone zinc(ii) derivatives for C–S cross-coupling reactions

2020 ◽  
Vol 44 (1) ◽  
pp. 129-140 ◽  
Author(s):  
Moulali Vaddamanu ◽  
Kavitha Velappan ◽  
Ganesan Prabusankar
Keyword(s):  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Highly Active

Mesoionic heavier chalcogenone complexes of zinc(ii) have been isolated and utilized as catalysts in C–S cross coupling reactions between thiophenols and aryl halides under convenient reaction conditions.

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.

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