Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 43, Pages 14212-14215Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808291
Keywords
endohedral functionalization; frustrated Lewis pairs; hemicryptophanes; homogeneous catalysis; supramolecular chemistry
Categories
Ask authors/readers for more resources
A frustrated Lewis pair (FLP) system was obtained by confinement of the Lewis base partner, a Verkade Q 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. P-31 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available