Rate and equilibrium constants for the addition of N-heterocyclic carbenes into benzaldehydes: a remarkable 2-substituent effect

Christopher John Collett, Richard S Massey, James Edward Taylor, Oliver R Maguire, AnnMarie C O'Donoghue*, Andrewv D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)
2 Downloads (Pure)

Abstract

Rate and equilibrium constants for the reaction between N-aryl triazolium 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.
Original languageEnglish
Pages (from-to)6887-6892
JournalAngewandte Chemie International Edition
Volume54
Issue number23
Early online date23 Apr 2015
DOIs
Publication statusPublished - 27 May 2015

Keywords

  • N-heterocyclic carbenes
  • Organocatalysis
  • Mechanistic studies
  • Kinetics
  • 2-substituent effect

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