Endohedral Functionalized Cage as a Tool to Create Frustrated Lewis Pairs

Angewandte Chemie
Jian YangAlexandre Martinez

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. 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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Citations

May 16, 2020·ChemPlusChem·Jean-Pierre Dutasta, Alexandre Martinez
Mar 22, 2019·Organic & Biomolecular Chemistry·Stéphane Le GacBernard Boitrel
Mar 28, 2019·Chemical Communications : Chem Comm·Sarah C BeteMatthias Otte
Feb 3, 2021·Chemistry : a European Journal·Natalie SchäferFlorian Beuerle
Dec 15, 2018·Organic Letters·Augustin LongAlexandre Martinez
Dec 18, 2021·Nature Chemistry·Rebecca CrawshawAnthony P Green

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