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.

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.

Liquid Crystal Phase Behavior of Novel Mesogenic Compound with Trifluoromethyl Substitutent

2013 ◽  
Vol 785-786 ◽  
pp. 680-683
Author(s):  
Yong Ming Zhang ◽  
Yi Wei Wang ◽  
Dan Dan Dang ◽  
Jie Si ◽  
Jian Fang Liu ◽  
...  
Keyword(s):  
Liquid Crystal ◽  
Coupling Reaction ◽  
Crystal Phase ◽  
Sonogashira Reaction ◽  
Sonogashira Coupling ◽  
Liquid Crystal Phase ◽  
Target Compound ◽  
Sonogashira Coupling Reaction ◽  
Phase Behaviors ◽  
Crystal Compound

In order to obtain a novel liquid crystal compound with trifluoromethyl substitutent, Sonogashira coupling reaction was used to synthesize the mesogenic compound based on tolane. Firstly, 1-iodo-4-trifluoromethyl-benzene was modified with acetylene groups, and then coupled with iodo amyl biphenyl through Sonogashira reaction to obtain the target compound. Moreover, the liquid crystal phase behaviors including transition temperatures and phase sequences were investigated by DSC and POM.

scholarly journals DNA-supported palladium nanoparticles as a reusable catalyst for the copper- and ligand-free Sonogashira reaction

2017 ◽  
Vol 7 (11) ◽  
pp. 2262-2273 ◽  
Author(s):  
Ana Silvia Camacho ◽  
Iris Martín-García ◽  
Claudia Contreras-Celedón ◽  
Luis Chacón-García ◽  
Francisco Alonso
Keyword(s):  
Heterogeneous Catalyst ◽  
Palladium Nanoparticles ◽  
Coupling Reaction ◽  
Sonogashira Reaction ◽  
Reusable Catalyst ◽  
Sonogashira Coupling ◽  
Mild Conditions ◽  
Sonogashira Coupling Reaction ◽  
Ligand Free ◽  
Supported Palladium

Palladium nanoparticles on DNA have been shown to be an effective and reusable heterogeneous catalyst for the copper- and ligand-free Sonogashira coupling reaction of aryl iodides under mild conditions in air.

ChemInform Abstract: 2,5-Bis(2-(diphenylphosphino)phenyl)-1,3,4-oxadiazole Ligands and Their Cu(I) Complexes for Sonogashira Coupling Reaction.

ChemInform ◽  
2014 ◽  
Vol 45 (35) ◽  
pp. no-no
Author(s):  
Cai-Xia Lin ◽  
Jia-Fang Zhu ◽  
Qing-Shan Li ◽  
Li-Hua Ao ◽  
Yan-Juan Jin ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Sonogashira Coupling Reaction

Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction

2021 ◽  
Vol 43 (1) ◽  
pp. 95-95
Author(s):  
Rifhat Bibi Rifhat Bibi ◽  
Muhammad Yaseen Muhammad Yaseen ◽  
Haseen Ahmad Haseen Ahmad ◽  
Ismat Ullah Khan Ismat Ullah Khan ◽  
Shaista Parveen Shaista Parveen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Terminal Alkynes ◽  
Vinyl Halides ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Alkyne Derivatives

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

scholarly journals The Utility of Sonogashira Coupling Reaction for the Derivatization of Aryl Halides with Fluorescent Alkyne

2018 ◽  
Vol 34 (10) ◽  
pp. 1183-1188 ◽  
Author(s):  
Naoyuki YASAKA ◽  
Naoya KISHIKAWA ◽  
Takumi HIGASHIJIMA ◽  
Kaname OHYAMA ◽  
Naotaka KURODA
Keyword(s):  
Coupling Reaction ◽  
Aryl Halides ◽  
Sonogashira Coupling ◽  
Sonogashira Coupling Reaction
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