scholarly journals Palladium-Catalyzed Mizoroki–Heck and Copper-Free Sonogashira Coupling Reactions in Water Using Thermoresponsive Polymer Micelles

Polymers ◽  
2021 ◽  
Vol 13 (16) ◽  
pp. 2717
Author(s):  
Noriyuki Suzuki ◽  
Shun Koyama ◽  
Rina Koike ◽  
Nozomu Ebara ◽  
Rikito Arai ◽  
...  
Keyword(s):  
Good Yield ◽  
Diblock Copolymers ◽  
Extraction Process ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Polymer Micelles ◽  
Heck Reactions ◽  
Thermoresponsive Polymer ◽  
Palladium Catalyzed ◽  
Efficient Extraction

A few kinds of thermoresponsive diblock copolymers have been synthesized and utilized for palladium-catalyzed coupling reactions in water. Poly(N-isopropylacrylamide) (PNIPAAm) and poly(N,N-diethylacrylamide) (PDEAAm) are employed for thermoresponsive segments and poly(sodium 4-styrenesulfonate) (PSSNa) and poly(sodium 2-acrylamido-methylpropanesulfonate) (PAMPSNa) are employed for hydrophilic segments. Palladium-catalyzed Mizoroki–Heck reactions are performed in water and the efficiency of the extraction process is studied. More efficient extraction was observed for the PDEAAm copolymers when compared with the PNIPAAm copolymers and conventional surfactants. In the study of the Sonogashira coupling reactions in water, aggregative precipitation of the products was observed. Washing the precipitate with water gave the product with satisfactory purity with a good yield.

Palladium-catalyzed Mizoroki-Heck reactions in water using thermoresponsive polymer micelles

Tetrahedron ◽  
2019 ◽  
Vol 75 (10) ◽  
pp. 1351-1358 ◽  
Author(s):  
Noriyuki Suzuki ◽  
Taiga Takabe ◽  
Yoshiko Yamauchi ◽  
Shun Koyama ◽  
Rina Koike ◽  
...  
Keyword(s):  
Polymer Micelles ◽  
Heck Reactions ◽  
Thermoresponsive Polymer ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Coupling Reactions: Carbonylative Heck Reactions to Give Chalcones.

ChemInform ◽  
2010 ◽  
Vol 41 (49) ◽  
pp. no-no
Author(s):  
Xiao-Feng Wu ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Coupling Reactions ◽  
Heck Reactions ◽  
Palladium Catalyzed

Palladium-Catalyzed Coupling Reactions: Carbonylative Heck Reactions To Give Chalcones

2010 ◽  
Vol 49 (31) ◽  
pp. 5284-5288 ◽  
Author(s):  
Xiao-Feng Wu ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Coupling Reactions ◽  
Heck Reactions ◽  
Palladium Catalyzed

Sonogashira coupling reactions: Synthesis of 4-substituted-6-methyl-2-(methylthio)pyrimidines catalyzed by Pd–Cu

2019 ◽  
Vol 43 (9-10) ◽  
pp. 431-436
Author(s):  
Fatemeh Rezaeimanesh ◽  
Mohammad Bakherad ◽  
Hossein Nasr-Isfahani
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Reaction Times ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Sonogashira Reactions

An efficient method is developed for the synthesis of 4-(3-arylprop-2-ynyloxy)-6-methyl-2-(methylthio)pyrimidines via palladium-catalyzed Sonogashira reactions of 4-methyl-2-(methylthio)-6-(prop-2-yn-1-yloxy)pyrimidine with electron-poor aryl iodides in acetonitrile at room temperature. Excellent yields of the products were obtained in reaction times of 9–11 h.

ChemInform Abstract: Improved Palladium-Catalyzed Sonogashira Coupling Reactions of Aryl Chlorides.

ChemInform ◽  
2009 ◽  
Vol 40 (21) ◽  
Author(s):  
Christian Torborg ◽  
Jun Huang ◽  
Thomas Schulz ◽  
Benjamin Schaeffner ◽  
Alexander Zapf ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Aryl Chlorides ◽  
Palladium Catalyzed

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.

Efficient synthesis of 2-phenyl-3-substituted furo/thieno[2,3-b]quinoxalines via Sonogashira coupling reaction followed by iodocyclization and subsequent palladium-catalyzed cross-coupling reactions

RSC Advances ◽  
2016 ◽  
Vol 6 (87) ◽  
pp. 83901-83908 ◽  
Author(s):  
Tayebeh Besharati-Seidani ◽  
Ali Keivanloo ◽  
Babak Kaboudin ◽  
Tsutomu Yokomatsu
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Efficient Synthesis ◽  
Cross Coupling Reactions ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed

In this paper, we report the successful synthesis of new 2-phenyl-3-substituted furo/thieno[2,3-b]quinoxaline derivatives from 2-chloro-3-methoxyquinoxaline and 2-chloro-3-(methylthio)quinoxaline by a three-step approach.

scholarly journals Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2293-2297 ◽  
Author(s):  
Allan Watson ◽  
Kirsty Wilson ◽  
Jane Murray ◽  
Helen Sneddon ◽  
Craig Jamieson
Keyword(s):  
Chemical Industry ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Heck Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

Palladium-catalyzed bond-forming reactions, such as the ­Suzuki–Miyaura and Mizoroki–Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki–Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47–91% yield), and Sonogashira (12 examples, 65–98% yield).

Palladium chemistry in recent porphyrin research

2004 ◽  
Vol 08 (01) ◽  
pp. 93-102 ◽  
Author(s):  
Jun-ichiro Setsune
Keyword(s):  
Supramolecular Assembly ◽  
Molecular Size ◽  
Sonogashira Coupling ◽  
Stille Coupling ◽  
Heck Reactions ◽  
Nano Scale ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Palladium Chemistry ◽  
Catalyzed Reactions

Palladium-catalyzed reactions such as Sonogashira coupling, Suzuki coupling, Stille coupling, Heck reactions, and Glaser-Hey oxidation were used to construct porphyrin modules of nano-scale molecular size in recent years. Recent developments in the supramolecular assembly of porphyrins and Pd (II) and in the organopalladium complexes of various porphyrins are also summarized.

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