scholarly journals Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

2019 ◽  
Vol 15 ◽  
pp. 2907-2913 ◽  
Author(s):  
László Orha ◽  
József M Tukacs ◽  
László Kollár ◽  
László T Mika
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Reaction Medium ◽  
Cross Coupling ◽  
Environmental Efficiency ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Mild Conditions ◽  
Palladium Catalyzed ◽  
Alternative Reaction Medium

It was demonstrated that the γ-valerolactone-based ionic liquid, tetrabutylphosphonium 4-ethoxyvalerate as a partially bio-based solvent can be utilized as alternative reaction medium for copper- and auxiliary base-free Pd-catalyzed Sonogashira coupling reactions of aryl iodides and functionalized acetylenes under mild conditions. Twenty-two cross-coupling products were isolated with good to excellent yields (72–99%) and purity (>98%). These results represent an example which proves that biomass-derived safer solvents can be utilized efficiently in common, industrially important transformations exhibiting higher chemical and environmental efficiency.

scholarly journals Tetrabutylphosphonium 4-ethoxyvalerate as a biomass-originated media for homogeneous palladium-catalyzed Hiyama coupling reactions

2020 ◽  
Vol 74 (12) ◽  
pp. 4593-4598
Author(s):  
László Orha ◽  
Ábrahám Papp ◽  
József M. Tukacs ◽  
László Kollár ◽  
László T. Mika
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Functional Group ◽  
Cross Coupling ◽  
Catalyst System ◽  
Catalyst Precursor ◽  
Coupling Reactions ◽  
Tetrabutylammonium Fluoride ◽  
Carbon Carbon Bonds ◽  
Palladium Catalyzed

Abstract The introduction of a biomass-derived ionic liquid into the Hiyama coupling reactions, which has been considered as a powerful tool for the synthesis of symmetrically and non-symmetrically substituted biaryl structures, could further control or even reduce the environmental impact of this transformation. It was shown that tetrabutylphosphonium 4-ethoxyvalerate, a γ-valerolactone-based ionic liquid, can be utilized as an alternative solvent to create carbon–carbon bonds between aryl iodides and functionalized organosilanes in the presence of 1 mol% Pd under typical Hiyama conditions (130 °C, 24 h, tetrabutylammonium fluoride activator). A comparison of different ionic liquids was performed, and the effects of the catalyst precursor and the moisture content of the reaction mixture on the activity of the catalyst system were investigated. The functional group tolerance was also studied, resulting in 15 cross-coupling products (3a–o) with isolated yields of 45–72% and excellent purity (> 98%).

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

2017 ◽  
Vol 41 (1) ◽  
pp. 372-376 ◽  
Author(s):  
Jinyi Song ◽  
Hongyan Zhao ◽  
Yang Liu ◽  
Huatao Han ◽  
Zhuofei Li ◽  
...  
Keyword(s):  
High Activity ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bidentate Ligands ◽  
Aryl Chlorides ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

A series of N,O-bidentate ligands were synthesized and studied as high activity ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions.

Ionophilic phosphonium-appended carbopalladacycle catalyst for Suzuki–Miyaura and Heck cross-coupling catalysis

2010 ◽  
Vol 88 (1) ◽  
pp. 27-34 ◽  
Author(s):  
Jocelyn J. Tindale ◽  
Paul J. Ragogna
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Catalyst Activity ◽  
Reaction Medium ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Phosphonium Salts ◽  
Transition Metal Catalyst ◽  
Imidazolium Ionic Liquids ◽  
Liquid Reaction

An ionic liquid, covalently tethered to an efficient transition-metal catalyst in the presence of an ionic liquid reaction medium, can utilize ionophilic interactions to improve catalyst activity, recyclability, and product isolation while decreasing catalyst leaching. Given the greater stability of phosphonium salts in comparison to imidazolium ionic liquids under basic conditions, phosphonium-tagged oxime carbopalladacycle salts were prepared and employed in both Heck and Suzuki–Miyaura reactions. The desired product was obtained in good yields for up to four catalyst cycles in the case of the Suzuki–Miyaura reaction. While taking advantage of the non-volatile nature of ionic liquids, the product was isolated through simple sublimation from the reaction mixture, eliminating issues associated with catalyst leaching, and the remaining ionic liquid solvent–catalyst mixture was ready for further catalysis.

Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: use of surfactants in cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (24) ◽  
pp. 18960-18971 ◽  
Author(s):  
Gina M. Roberts ◽  
Wenya Lu ◽  
L. Keith Woo
Keyword(s):  
Aqueous Solutions ◽  
Organic Solvents ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Bromide ◽  
Sonogashira Coupling ◽  
Mild Conditions ◽  
Cross Coupling Reactions

Aqueous solutions of common and inexpensive surfactants (e.g. SDS and CTAB) are surveyed as an alternative to organic solvents in Sonogashira cross-coupling. Aryl-bromide substrates are best coupled under Cu-free conditions.

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