Synthesis of PEG-supported organotrifluoroborates and their applications in palladium-catalyzed homo-coupling reactions

2015 ◽  
Vol 44 (10) ◽  
pp. 4759-4764
Author(s):  
Li Yong ◽  
Min-Liang Yao ◽  
David W. Blevins ◽  
George W. Kabalka
Keyword(s):  
Room Temperature ◽  
Water Soluble ◽  
Coupling Reactions ◽  
Synthetic Route ◽  
Palladium Catalyzed

A general synthetic route to water-soluble PEG-supported organotrifluoroborates has been developed. In the presence of air and catalytic amounts of Pd(OAc)2, the PEG-supported organotrifluoroborates undergo homo-coupling reactions smoothly at room temperature.

Water-Soluble Imine Ligand/Palladium-Catalyzed Suzuki Reaction at Room Temperature

2010 ◽  
Vol 31 (10) ◽  
pp. 1277-1280
Author(s):  
Chun LIU ◽  
Qijian NI ◽  
Pingping HU ◽  
Hao YUAN ◽  
Zilin JIN
Keyword(s):  
Room Temperature ◽  
Suzuki Reaction ◽  
Water Soluble ◽  
Palladium Catalyzed

A new procedure for the synthesis of water-soluble tri-cationic and -anionic phthalocyanines

2005 ◽  
Vol 09 (09) ◽  
pp. 651-658 ◽  
Author(s):  
Wesley M. Sharman ◽  
Johan E. van Lier
Keyword(s):  
Photodynamic Therapy ◽  
Ring Expansion ◽  
Water Soluble ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Zinc Phthalocyanines ◽  
Palladium Catalyzed ◽  
Metal Insertion ◽  
Ring Expansion Reaction

A series of water-soluble tri-anionic and -cationic substituted phthalocyanines has been synthesized via iodinated boron subphthalocyanines. The latter were opened with differently substituted diiminoisoindolines via the Kobayashi ring expansion reaction followed by metal insertion to exclusively yield the asymmetrically 3:1 substituted iodinated zinc phthalocyanines. These iodinated phthalocyanines readily underwent palladium-catalyzed coupling reactions with terminal alkynes such as 5-hexynoic acid and 10-undecynoic acid to give anionic phthalocyanines, or with 2-ethynylpyridine and 3-ethynylpyridine followed by N -methylation to give cationic phthalocyanines. These novel asymmetrically substituted charged phthalocyanines could have interesting properties as photosensitizers for photodynamic therapy.

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.

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