Rate and Equilibrium Constants for the Addition of N-Heterocyclic Carbenes into Benzaldehydes: A Remarkable 2-Substituent Effect.
Angew Chem Weinheim Bergstr Ger
; 127(23): 6991-6996, 2015 Jun 01.
Article
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| MEDLINE
| ID: mdl-27478264
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.
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1
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01-internacional
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MEDLINE
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En
Revista:
Angew Chem Weinheim Bergstr Ger
Asunto de la revista:
BIOFISICA
/
QUIMICA
Año:
2015
Tipo del documento:
Article