Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration

Abstract : N-heterocyclic carbene-capped cyclodextrin (ICyD) ligands, α-ICyD and β-ICyD derived from α- and β-cyclodextrin, respectively give opposite regioselectivities in a copper-catalyzed hydroboration. The site-selectivity results from two different mechanisms: the conventional parallel one and a new orthogonal mechanism. The shape of the cavity was shown not only to induce a regioselectivity switch but also a mechanistic switch. The scope of interest of the encapsulation of a reactive center is therefore broadened by this study.
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Pinglu Zhang, Jorge Meijide suárez, Thomas Driant, Etienne Derat, Yongmin Zhang, et al.. Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration. Angewandte Chemie, Wiley-VCH Verlag, 2017, 129 (36), pp.10961 - 10965. ⟨10.1002/ange.201705303⟩. ⟨hal-01593597⟩

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