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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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.
Original languageEnglish
Article number202100384
Pages (from-to)3670-3675
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number26
Early online date31 May 2021
DOIs
Publication statusPublished - 15 Jul 2021

Keywords

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

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