Role of Ion-Pairs in Brønsted Acid Catalysis

Heejae Kim, Erli Sugiono, Yuki Nagata, Manfred Wagner, Mischa Bonn, Magnus Rueping, Johannes Hunger*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Phosphoric acids have emerged as efficient organo-catalysts for various reactions. Despite widespread use, details of the reaction intermediates giving rise to stereocontrol have remained elusive. To clarify the nature of the catalyst-substrate interaction, we characterize and quantify catalyst-substrate complex formation by combining dielectric spectroscopy, quantum chemistry, and 1H NMR spectroscopy. For a series of different solvents, the interaction between substrate and catalyst is dominated by ion-pairing, rather than hydrogen bonding, at ambient conditions. Correlation of ion association with catalytic enantioselectivity provides evidence that close-contact ion-pairing is essential for stereocontrol and that dissociation into free ions dramatically reduces enantioselectivity.

Original languageEnglish (US)
Pages (from-to)6630-6633
Number of pages4
JournalACS Catalysis
Volume5
Issue number11
DOIs
StatePublished - Nov 6 2015
Externally publishedYes

Keywords

  • asymmetric catalysis
  • dielectric spectroscopy
  • enantioselectivity
  • ion-pairing
  • organo-catalysis
  • phosphoric acids
  • quantum chemical calculation

ASJC Scopus subject areas

  • Catalysis

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