Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration.

ABSTRACT

N-heterocyclic carbene-capped cyclodextrin (ICyD) ligands, α-ICyD and ß-ICyD derived from α- and ß-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.