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Accueil du site > Production scientifique > The Intermediates in Lewis Acid Catalysis with Lanthanide Triflates

The Intermediates in Lewis Acid Catalysis with Lanthanide Triflates

Date de publication: 25 avril 2019

GL. Tripodi ; TC. Correra ; CFF. Angolini ; BRV. Ferreira ; P. Maitre ; MN. Eberlin ; J. Roithova
Eur. J. Org. Chem. 22 3560-3566 (2019). DOI

Travail réalisé sur le site de l’Université Paris Sud.

Abstract

Lanthanide triflates are effective Lewis acid catalysts in reactions involving carbonyl compounds due to their high oxophilicity and water stability. Despite the growing interest, the identity of the catalytic species formed in lanthanide catalysed reactions is still unknown. We have therefore used mass spectrometry and ion spectroscopy to intercept and characterize the intermediates in a reaction catalysed by ytterbium and dysprosium triflates. We were able to identify a number of lanthanide intermediates formed in a simple condensation reaction between a C-acid and an aldehyde. Results show correlation between the reactivity of lanthanide complexes and their charge state and suggest that the triply charged complexes play a key role in lanthanide catalysed reactions. Spectroscopic data of the gaseous ions accompanied by theoretical calculations reveal that the difference between catalytic efficiencies of ytterbium and dysprosium ions can be explained by their different electrophilicity.