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. 2018 Jul 20:14:1846-1853.
doi: 10.3762/bjoc.14.158. eCollection 2018.

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

Antony Wing Hung Ng  1 , Chi-Chung Yee  1 , Kai Wang  1 , Ho Yu Au-Yeung  1
Affiliations

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

Antony Wing Hung Ng et al. Beilstein J Org Chem. .

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.

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Figures

Scheme 1
Scheme 1
Diazide and dialkyne building blocks used in this study.
Scheme 2
Scheme 2
Synthesis of Cat-1 by CBAAC. aAssembly yield by HPLC; bisolated yield as PF6− salt.
Scheme 3
Scheme 3
Synthesis of [3]catenanes by CBAAC. aAssembly yield by HPLC; bisolated yield by precipitation as PF6− salt; cisolated yield by preparative HPLC.
Figure 1
Figure 1
1H NMR (500 MHz, D2O, 298 K) of Cat-2. The signal at ca. 8.3 ppm is the residual formate from preparative HPLC.
Figure 2
Figure 2
(a) ESIMS, (b) HRMS, and (c) MS2 spectrum (parent ion at m/z = 887.8) of Cat-2.
Scheme 4
Scheme 4
Synthesis of the [4]catenane Cat-11. aAssembly yield by HPLC; bisolated yield by preparative HPLC.
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