Authors: Gottardo, Christine; Kraft, Thomas M.; Hossain, M S.; Zawada, Peter V.; Muchall, Heidi M.

Source: Canadian Journal of Chemistry, Volume 86, Number 5, May 2008 , pp. 410-415(6)

Publisher: NRC Research Press

Abstract:

Relative rate constants (k_rel) 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.

On a déterminé les constantes de vitesses relatives (k_rel) pour le couplage de Sonogashira dans des réactions compétitives entre l'iodobenzène et une série d'iodobenzènes substitués en positions méta et para et on a les a comparées à la charge sur l'iode et au composant z du moment quadripolaire du carbone portant l'iode. On a utilisé une analyse par corrélation de Hammett et des données de calculs théoriques pour obtenir d'autres bases pour établir que l'étape cinétiquement limitante de la réaction de Sonogashira est l'addition initiale oxydante du palladium sur la liaison carbone-iode. Mots-clés : Sonogashira, réactions compétitives, corrélation de Hammett. [Traduit par la Rédaction]

Document Type: Research article

Publication date: 2008-05-01

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