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

Collett, Christopher J.; Young, Claire M.; Massey, Richard S.; O'Donoghue, AnnMarie C.; Smith, Andrew D

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


Authors

Christopher J. Collett

Claire M. Young

Richard S. Massey

Andrew D Smith



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.

Journal Article Type Article
Online Publication Date May 31, 2021
Publication Date Jul 15, 2021
Deposit Date May 7, 2021
Publicly Available Date Jul 6, 2021
Journal European Journal of Organic Chemistry
Print ISSN 1434-193X
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2021
Issue 26
Pages 3670-3675
DOI https://doi.org/10.1002/ejoc.202100384
Public URL https://durham-repository.worktribe.com/output/1248390
Publisher URL https://doi.org/10.1002/ejoc.202100384

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Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/

Copyright Statement
Early view © 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.






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