High yielding synthesis of 2,2′-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes

J. E.M. Lewis, R. J. Bordoli, M. Denis, C. J. Fletcher, M. Galli, E. A. Neal, E. M. Rochette, S. M. Goldup*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

Abstract

We present an operationally simple approach to 2,2′-bipyridine macrocycles. Our method uses simple starting materials to produce these previously hard to access rotaxane precursors in remarkable yields (typically >65%) across a range of scales (0.1-5 mmol). All of the macrocycles reported are efficiently converted (>90%) to rotaxanes under AT-CuAAC conditions. With the requisite macrocycles finally available in sufficient quantities, we further demonstrate their long term utility through the first gram-scale synthesis of an AT-CuAAC [2]rotaxane and extend this powerful methodology to produce novel Sauvage-type molecular shuttles.

Original languageEnglish
Pages (from-to)3154-3161
Number of pages8
JournalChemical Science
Volume7
Issue number5
DOIs
Publication statusPublished - 2016

Bibliographical note

Funding Information:
We thank Fluorochem for the gift of reagents, the EPSRC National Mass Spectrometry Service for HRMS analysis and the EPSRC (EP/L016621/1), Queen Mary, University of London and the University of Southampton for funding. JEML is a European Commission Marie Sklodowska-Curie Fellow. SMG is a Royal Society Research Fellow. This project has received funding from the European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement No 660731.

Publisher Copyright:
© 2016 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • General Chemistry

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