Kinetic and Structure‐Activity Studies of the Triazolium Ion‐ Catalyzed Intramolecular Stetter Reaction
European Journal of Organic Chemistry ; doi:10.1002/ejoc.202100384
Abstract: Mechanistic studies of the triazolium ion‐catalyzed intramolecular Stetter reaction using initial rates analysis in NEt 3 /NEt 3 .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.
Keywords: NHC / Breslow intermediate / triazolium / Stetter reaction / initial rates analysis
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