Kinetic and structure-activity studies of the triazolium Ion-catalyzed intramolecular stetter reaction
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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.
Collett , C J , Young , C M , Massey , R S , O'Donoghue , A & Smith , A D 2021 , ' Kinetic and structure-activity studies of the triazolium Ion-catalyzed intramolecular stetter reaction ' , European Journal of Organic Chemistry , vol. 2021 , no. 26 , 202100384 , pp. 3670-3675 . https://doi.org/10.1002/ejoc.202100384
European Journal of Organic Chemistry
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