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

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

doi:10.1002/anie.201101385

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 journal › Article › peer-review

97 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 language	English (US)
Pages (from-to)	6364-6369
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	28
DOIs	https://doi.org/10.1002/anie.201101385
State	Published - Jul 4 2011
Externally published	Yes

Keywords

Brønsted acids
NMR spectroscopy
activation
imines
organocatalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201101385

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AU - Gschwind, Ruth M.

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KW - NMR spectroscopy

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KW - organocatalysis

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

Abstract

Keywords

ASJC Scopus subject areas

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