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Kinetic and Structure–Activity Studies of the Triazolium Ion– catalyzed Intramolecular Stetter Reaction

Collett, Christopher J. and Young, Claire M. and Massey, Richard S. and O'Donoghue, AnnMarie C. and Smith, Andrew D (2021) 'Kinetic and Structure–Activity Studies of the Triazolium Ion– catalyzed Intramolecular Stetter Reaction.', European Journal of Organic Chemistry, 2021 (26). pp. 3670-3675.


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.

Item Type:Article
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Publisher statement:© 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Date accepted:No date available
Date deposited:10 May 2021
Date of first online publication:31 May 2021
Date first made open access:06 July 2021

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