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Article Dans Une Revue Angewandte Chemie International Edition Année : 2018

Endohedral Functionalized Cage as a Tool to Create Frustrated Lewis Pairs

Résumé

A frustrated Lewis pair (FLP) system was obtained by confinement of the Lewis base partner, a Verkades super-base, 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. 31 P 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.
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Dates et versions

hal-01896309 , version 1 (06-04-2019)

Identifiants

Citer

Jian Yang, Bastien Chatelet, Véronique Dufaud, Damien Herault, Sabine Michaud-Chevallier, et al.. Endohedral Functionalized Cage as a Tool to Create Frustrated Lewis Pairs. Angewandte Chemie International Edition, 2018, 57 (43), pp.4212-14215. ⟨10.1002/anie.201808291⟩. ⟨hal-01896309⟩
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