AIBN-initiated radical addition of gem-difluorinated alkyl iodides to alkynes and the Pd-catalyzed Sonogashira coupling reaction of E-phenyl difluoromethylene vinylic iodides with terminal alkynes

Tetrahedron ◽  
2007 ◽  
Vol 63 (43) ◽  
pp. 10684-10692 ◽  
Author(s):  
Xiang Fang ◽  
Xueyan Yang ◽  
Xianjin Yang ◽  
Shenjie Mao ◽  
Zhonghua Wang ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Radical Addition ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Sonogashira Coupling Reaction ◽  
Alkyl Iodides

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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