Gottardo, Christine and Kraft, Thomas M. and Hossain, M. Selim and Zawada, Peter V. and Muchall, Heidi M. (2008) Linear free-energy correlation analysis of the electronic effects of the substituents in the Sonogashira coupling reaction. Canadian Journal of Chemistry, 86 (5). 410-415 . ISSN 0008-4042
- Published Version
Official URL: http://dx.doi.org/10.1139/V08-038
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.
|Divisions:||Concordia University > Faculty of Arts and Science > Chemistry and Biochemistry|
|Authors:||Gottardo, Christine and Kraft, Thomas M. and Hossain, M. Selim and Zawada, Peter V. and Muchall, Heidi M.|
|Journal or Publication:||Canadian Journal of Chemistry|
|Digital Object Identifier (DOI):||10.1139/V08-038|
|Keywords:||Sonogashira, competitive reactions, Hammett correlation|
|Deposited By:||DANIELLE DENNIE|
|Deposited On:||12 Jul 2010 20:27|
|Last Modified:||24 Aug 2016 21:26|
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