Improved Synthesis of Monohalogenated Cavitands and Their Use in the Synthesis of Further Functionalized Cavitands

Abstract

A new procedure for the synthesis of monohalogenated cavitands was established, which is at least one step shorter and far more atom-efficient than previously published pathways. These monohalogenated cavitands were demonstrated to be versatile synthons for the synthesis of further functionalized derivatives through cyanation, carboxylation, and a series of palladium-catalyzed Suzuki reactions.

Efficient resolution of racemic crown-shaped cyclotriveratrylene derivatives and isolation and characterization of the intermediate saddle isomer

“…Due to our interest in dissymmetric [29–36] and concave molecular building blocks [37] and their implementation in supramolecular architectures like (allosteric) receptors [38–44] or metallosupramolecular helicates and cages [45–57] we were intrigued by the class of chiral CTVs. This is especially true for derivative 1 (Scheme 2) due to its interesting trifold substitution pattern with an almost orthogonal orientation of the functional groups which make it an ideal precursor for the synthesis of other elaborated derivatives [58–59] and the ease of a recently established large-scale synthesis reported by Rousseau and co-workers [60].…”