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- Title
Rate and Equilibrium Constants for the Addition of N-Heterocyclic Carbenes into Benzaldehydes: A Remarkable 2-Substituent Effect.
- Authors
Collett, Christopher J.; Massey, Richard S.; Taylor, James E.; Maguire, Oliver R.; O'Donoghue, AnnMarie C.; Smith, Andrew D.
- Abstract
Rate and equilibrium constants for the reaction between N-aryl triazolium N-heterocyclic carbene (NHC) precatalysts and substituted benzaldehyde derivatives to form 3-(hydroxybenzyl)azolium adducts under both catalytic and stoichiometric conditions have been measured. Kinetic analysis and reaction profile fitting of both the forward and reverse reactions, plus onwards reaction to the Breslow intermediate, demonstrate the remarkable effect of the benzaldehyde 2-substituent in these reactions and provide insight into the chemoselectivity of cross-benzoin reactions.
- Subjects
CARBENES; HETEROCYCLIC compounds; BENZALDEHYDE; CHEMICAL reactions; ARYL group
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 23, p6991
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201501840