ArticleMolecules (Basel, Switzerland)2017
Stepwise, Protecting Group Free Synthesis of [4]Rotaxanes.
Article in Molecules (Basel, Switzerland), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed.
- Active Templating by Mechanochemistry.Organic letters · 2026Article
- Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction.Angewandte Chemie (International ed. in English) · 2019Article
- Chelating Rotaxane Ligands as Fluorescent Sensors for Metal Ions.Angewandte Chemie (International ed. in English) · 2018Article
- Efficient Multicomponent Active Template Synthesis of Catenanes.Journal of the American Chemical Society · 2018Article
- Porphyrinoid rotaxanes: building a mechanical picket fence.Chemical science · 2017Article
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3 authors.
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Abstract
Despite significant advances in the last three decades towards high yielding syntheses of rotaxanes, the preparation of systems constructed from more than two components remains a challenge. Herein we build upon our previous report of an active template copper-catalyzed azide-alkyne cycloaddition (CuAAC) rotaxane synthesis with a diyne in which, following the formation of the first mechanical bond, the steric bulk of the macrocycle tempers the reactivity of the second alkyne unit. We have now extended this approach to the use of 1,3,5-triethynylbenzene in order to successively prepare [2]-, [3]- and [4]rotaxanes without the need for protecting group chemistry. Whilst the first two iterations proceeded in good yield, the steric shielding that affords this selectivity also significantly reduces the efficacy of the active template (AT)-CuAAC reaction of the third alkyne towards the preparation of [4]rotaxanes, resulting in severely diminished yields.
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