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Kinetic and structure-activity studies of the triazolium Ion-catalyzed intramolecular stetter reaction

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Author(s)

Christopher John Collett, Claire Mary Young, Richard. S. Massey, AnnMarie O'Donoghue, Andrew David Smith

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Abstract

Mechanistic studies of the triazolium ion‐catalyzed intramolecular Stetter reaction using initial rates analysis in NEt3/NEt3. HCl buffered methanol showed the reaction to be first order in catalyst and zero order in aldehyde over a broad range of aldehyde concentrations. The observed reaction rate is higher for catalysts bearing N‐aryl substituents with electron‐withdrawing groups. A concurrent, NHC‐independent substrate isomerization was also observed and found to demonstrate a first order dependence on aldehyde concentration. The reported data are consistent with deprotonation to form the Breslow intermediate being turnover‐limiting in this process.
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Details

Original languageEnglish
Article number202100384
Number of pages7
JournalEuropean Journal of Organic Chemistry
VolumeEarly View
Early online date31 May 2021
DOIs
Publication statusE-pub ahead of print - 31 May 2021

    Research areas

  • NHC, Breslow intermediate, Triazolium, Stetter reaction, Initial rates analysis

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