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- Title
Endohedral Functionalized Cage as a Tool to Create Frustrated Lewis Pairs.
- Authors
Yang, Jian; Chatelet, Bastien; Hérault, Damien; Michaud‐Chevallier, Sabine; Martinez, Alexandre; Dufaud, Véronique; Robert, Vincent; Dutasta, Jean‐Pierre
- Abstract
A frustrated Lewis pair (FLP) system was obtained by confinement of the Lewis base partner, a Verkade's superbase, in a molecular cavity. Whereas the model superbase lacking cavity displayed no catalytic activity in Morita–Baylis–Hillman (MBH) reactions, when associated to titanium (IV) chloride, the encaged superbase turns out to be an efficient catalyst under the same conditions. The crucial role of the endohedral functionalized cage on catalytic performance was further demonstrated by the fact that model superbases with bulky substituents were much less efficient to produce active catalysts, as well as by inhibition and substrate selection experiments. 31P NMR spectroscopy and mass spectrometry experiments evidenced that no interaction between the Lewis acidic and basic partners occurred when the superbase was capped by a cycloveratrylene (CTV) unit, thus creating a true FLP active system.
- Subjects
LEWIS pairs (Chemistry); BAYLIS-Hillman reaction; CATALYTIC activity; SUPERBASES (Chemistry); NUCLEAR magnetic resonance spectroscopy
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 43, p14408
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201808291