A coordination driven self-assembled Pd6L8 nanoball catalyses copper and phosphine-free Sonogashira coupling reaction in both homogeneous and heterogeneous formats

2016 ◽  
Vol 40 (8) ◽  
pp. 7140-7147 ◽  
Author(s):  
Subhashis Pradhan ◽  
Subhadip Dutta ◽  
Rohith P. John
Keyword(s):  
Aqueous Medium ◽  
Coupling Reaction ◽  
Sonogashira Reaction ◽  
Catalyst Loading ◽  
Sonogashira Coupling ◽  
Aerobic Conditions ◽  
Homogeneous Phase ◽  
Sonogashira Coupling Reaction ◽  
Self Assembled ◽  
Heterogeneous Phase

A self-assembled Pd6L8 nanocage catalysed copper free Sonogashira reaction under mild and aerobic conditions, at 100 ppm catalyst loading in aqueous medium in the homogeneous phase, and at 500 ppm in the heterogeneous phase.

scholarly journals Tetradentate Palladium(II) Salophen Complexes: Synthesis, Characterization and Catalytic Activities in Copper-Free Sonogashira Coupling Reaction

2018 ◽  
Vol 7 (3.11) ◽  
pp. 15 ◽  
Author(s):  
Shahrul Nizam Ahmad ◽  
Hadariah Bahron ◽  
Amalina Mohd Tajuddin
Keyword(s):  
Condensation Reaction ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Insertion Reaction ◽  
Catalyst Loading ◽  
Sonogashira Coupling ◽  
1H And 13C Nmr ◽  
Catalytic Activities ◽  
Sonogashira Coupling Reaction

This paper reports the synthesis and characterization of three salophen ligands; 2,2'-((1E,1'E)-(1,2 phenylenebis(azanylylidene))bis(methanylylidene))diphenol [L1H], 2,2'-((1E,1'E)-(1,2-phenylenebis(azanylylidene))bis (methanylylidene))bis(4-chlorophenol) [L1C] and 2,2'-((1E,1'E)-(1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-methoxylphenol) [L1OME]. The compounds were prepared from condensation reaction between salicylaldehyde, and its derivatives, with ortho-phenylenediamine. Their palladium(II) complexes, namely PdL1H, PdL1C and PdL1OME were synthesized through insertion reaction between the ligands with palladium(II) acetate. All compounds were characterized through melting point, elemental analysis, infrared spectroscopy, 1H and 13C NMR spectroscopy. Palladium(II) complexes were tested as homogenous catalysts in copper-free Sonogashira coupling reaction between iodobenzene and phenylacetylene in DMSO using triethylamine as base with 1.0 mmol% catalyst loading. The most performing catalyst was PdL1OME with 91% conversion followed by PdL1H (83%) and PdL1C (27%).   

scholarly journals Linear free-energy correlation analysis of the electronic effects of the substituents in the Sonogashira coupling reaction

2008 ◽  
Vol 86 (5) ◽  
pp. 410-415 ◽  
Author(s):  
Christine Gottardo ◽  
Thomas M Kraft ◽  
M Selim Hossain ◽  
Peter V Zawada ◽  
Heidi M Muchall
Keyword(s):  
Correlation Analysis ◽  
Relative Rate ◽  
Coupling Reaction ◽  
Sonogashira Reaction ◽  
Sonogashira Coupling ◽  
Electronic Effects ◽  
Linear Free Energy ◽  
Competitive Reactions ◽  
Sonogashira Coupling Reaction ◽  
Hammett Correlation

Relative rate constants (krel) for the Sonogashira coupling were determined in competitive reactions between iodobenzene and a series of para- and meta-substituted iodobenzenes and compared to the charge on iodine and the z-component of the quadrupole moment of the iodine-bearing carbon. We use an Hammett correlation analysis and the computational data to provide further evidence that the rate limiting step of the Sonogashira reaction is the initial oxidative addition of Pd to the carbon-iodine bond.Key words: Sonogashira, competitive reactions, Hammett correlation.

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