Efficient catenane synthesis by cucurbit[6]uril-mediated azide–alkyne cycloaddition

Abstract

We report here the efficient synthesis of a series of [3]catenanes featuring the use of cucurbit[6]uril to simultaneously mediate the mechanical and covalent bond formations. By coupling the mechanical interlocking with covalent macrocyclization, formation of topological isomers is eliminated and the [3]catenanes are formed exclusively in good yields. The efficient access to these [3]catenanes and the presence of other recognition units render them promising building blocks for the construction of other high-order interlocked structures.

Keywords

• azide–alkyne cycloaddition
• catenane
• click chemistry
• cucurbit[6]uril
• mechanical bond