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

Christine Gottardo, Thomas M. Kraft, M. Selim Hossain, Peter V. Zawada, Heidi M. Muchall

Research output: Contribution to journalArticleScientificpeer-review

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)410-415
Number of pages6
JournalCanadian Journal of Chemistry
Volume86
Issue number5
DOIs
Publication statusPublished - 1 May 2008
MoE publication typeA1 Journal article-refereed

Keywords

  • Competitive reactions
  • Hammett correlation
  • Sonogashira

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