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

Title:

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

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

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Official URL: http://dx.doi.org/10.1139/V08-038

Abstract

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
Item Type:Article
Refereed:Yes
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
Date:May 2008
Funders:
  • Natural Sciences and Engineering Research Council of Canada
Keywords:Sonogashira, competitive reactions, Hammett correlation
ID Code:6761
Deposited By:DANIELLE DENNIE
Deposited On:12 Jul 2010 16:27
Last Modified:08 Dec 2010 18:09
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