Cyclodextrins (CDs) are concave molecules, which contain a hydrophobic cavity and a hydrophilic outer layer. Previous research from the Sollogoub group has shown that subsequent metallation of NHC-capped-cyclodextrin-ligands coined ICyDs derived from regioselectively deprotected perbenzylated cyclodextrins gave access to original metal catalysts, mimicking metalloenzyme active sites. Enzymes present a hydrophobic channel favoring substrate approach, but also a protein pocket surrounding their active site, where amino acids are able to stabilize by weak interactions the substrate and to direct the efficiency and the selectivity of the reaction. The NHC-CD metal complexes (with M= Ag, Cu, Au) are the first examples of a metal encapsulated right in the center of the CD cavity. The confinement of the metal provides it with an original set of interactions with the wall of the cavity, specifically interactions with benzyl groups on the secondary rim of the CD. Research suggests that these interactions likely interfere with the reactive species inside the cavity in a manner still to be understood. The aim of the project is to synthesize a new NHC-bridged a-CD metal complex bearing methyl ether groups on its secondary rim instead of the original benzyl groups to determine whether the interactions with the ligands and the selectivity in catalysis would be altered by this sterical/electronic change in order to evaluate the role played by this second coordination sphere.

Synthesis of functionalized NHC-capped α-cyclodextrin metal complexes

253rd National Meeting (2017)

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