Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6

2005 ◽  
Vol 83 (6-7) ◽  
pp. 711-715 ◽  
Author(s):  
Takahide Fukuyama ◽  
Ryo Yamaura ◽  
Ilhyong Ryu
Keyword(s):  
Ionic Liquid ◽  
Reaction Medium ◽  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Low Viscosity ◽  
Aryl Iodides ◽  
Sonogashira Coupling Reaction ◽  
Three Component Coupling

A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.Key words: carbonylation, palladium, three-component coupling, ionic liquid, α,β-acetylenic ketones.

Microwave-assisted, Copper-free Sonogashira Coupling between Aryl Halides and Terminal Alkynes Using Recyclable Ionic Liquid and Catalyst.

2021 ◽  
Vol 18 ◽  
Author(s):  
Dau Xuan Duc ◽  
Nguyen Van Quoc
Keyword(s):  
Ionic Liquid ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Considerable Decrease ◽  
Short Reaction Time ◽  
Microwave Assisted ◽  
Sonogashira Coupling Reaction ◽  
High Yields

: An efficient method for the Sonogashira coupling reaction between aryl halides and terminal alkynes has been developed. The reaction was performed in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim][BF4]) under microwave irradiation. High yields of products were obtained in very short reaction time. Moreover, the medium and catalyst could be recovered and reused three times without considerable decrease in reaction yields.

CuI/PPh3-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes in water in the absence of palladium

2009 ◽  
Vol 23 (2) ◽  
pp. 75-77 ◽  
Author(s):  
Jin Tao Guan ◽  
Guang-Ao Yu ◽  
Lei Chen ◽  
Tan Qing Weng ◽  
Jing Jing Yuan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Aryl Iodides ◽  
Sonogashira Coupling Reaction

ChemInform Abstract: FeCl3/PPh3-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides with Terminal Alkynes.

ChemInform ◽  
2010 ◽  
Vol 41 (34) ◽  
pp. no-no
Author(s):  
Dinesh N. Sawant ◽  
Pawan J. Tambade ◽  
Yogesh S. Wagh ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Aryl Iodides ◽  
Sonogashira Coupling Reaction

FeCl3/PPh3-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes

2010 ◽  
Vol 51 (20) ◽  
pp. 2758-2761 ◽  
Author(s):  
Dinesh N. Sawant ◽  
Pawan J. Tambade ◽  
Yogesh S. Wagh ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Aryl Iodides ◽  
Sonogashira Coupling Reaction

Environmentally Benign Microwave-Assisted Sonogashira Preparation of Aromatic Compounds

2011 ◽  
Vol 695 ◽  
pp. 113-116 ◽  
Author(s):  
Suttikiat Puechmongkol ◽  
Boonchoat Paosawatyanyong ◽  
Worawan Bhanthumnavin
Keyword(s):  
Coupling Reaction ◽  
Environmentally Benign ◽  
Conventional Heating ◽  
Microwave Activation ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Aryl Bromides ◽  
Sonogashira Coupling Reaction ◽  
Type Coupling

An efficient Sonogashira-type coupling reaction of terminal alkynes and aryl bromides by microwave activation with short reaction time under mild conditions are presented. It is illustrated herein that the traditional Sonogashira coupling reaction can be achieved with a much more efficient yet environmentally friendly condition. In contrary to the usually required 10 mol% Pd loading and the use of conventional heating at 60 °C for 24 h in order for a reaction to proceed satisfactorily, with a 100 W microwave activation, the reaction of terminal alkynes with substituted aryl bromides can be achieved with only a 2.5 mol% Pd in 10 min. The yield was improved with microwave irradiation.

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