Brønsted acid catalysis: Hydrogen bonding versus ion pairing in imine activation

Matthias Fleischmann, Diana Drettwan, Erli Sugiono, Magnus Rueping*, Ruth M. Gschwind

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

89 Scopus citations

Abstract

Behind the scenes: NMR spectroscopy was used to distinguish hydrogen bonding and ion pairing in the activation of imines by a phosphate catalyst (see structures). Hydrogen-bond strength and the amount of the hydrogen-bonded species present are decisive for the catalytic reaction and can be manipulated by introducing substituents with different electronic properties. This insight should guide the development of more efficient catalytic systems.

Original languageEnglish (US)
Pages (from-to)6364-6369
Number of pages6
JournalAngewandte Chemie - International Edition
Volume50
Issue number28
DOIs
StatePublished - Jul 4 2011

Keywords

  • Brønsted acids
  • NMR spectroscopy
  • activation
  • imines
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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