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

doi:10.1039/c6sc00011h

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

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	3154-3161
Number of pages	8
Journal	Chemical Science
Volume	7
Issue number	5
DOIs	https://doi.org/10.1039/c6sc00011h
Publication status	Published - 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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title = "High yielding synthesis of 2,2′-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes",

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.",

author = "Lewis, \{J. E.M.\} and Bordoli, \{R. J.\} and M. Denis and Fletcher, \{C. J.\} and M. Galli and Neal, \{E. A.\} and Rochette, \{E. M.\} and Goldup, \{S. M.\}",

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: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6sc00011h",

language = "English",

volume = "7",

pages = "3154--3161",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "5",

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T1 - High yielding synthesis of 2,2′-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes

AU - Lewis, J. E.M.

AU - Bordoli, R. J.

AU - Denis, M.

AU - Fletcher, C. J.

AU - Galli, M.

AU - Neal, E. A.

AU - Rochette, E. M.

AU - Goldup, S. M.

N1 - 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.

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84966397066

U2 - 10.1039/c6sc00011h

DO - 10.1039/c6sc00011h

M3 - Article

AN - SCOPUS:84966397066

SN - 2041-6520

VL - 7

SP - 3154

EP - 3161

JO - Chemical Science

JF - Chemical Science

IS - 5

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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