High yielding synthesis of 2,2'-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes
High yielding synthesis of 2,2'-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes
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.
Lewis, J.E.M
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Bordoli, R. J.
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Denis, M.
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Fletcher, C.J.
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Galli, M.
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Neal, E. A.
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Rochette, E.A.
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Goldup, SM.
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Lewis, J.E.M
42b46a03-a7ca-4d3a-96e5-a5c962fc9573
Bordoli, R. J.
f7f925e7-08fc-4b62-97bb-647ecf8b8751
Denis, M.
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Fletcher, C.J.
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Galli, M.
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Neal, E. A.
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Rochette, E.A.
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Goldup, SM.
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Lewis, J.E.M, Bordoli, R. J., Denis, M., Fletcher, C.J., Galli, M., Neal, E. A., Rochette, E.A. and Goldup, SM.
(2016)
High yielding synthesis of 2,2'-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes.
Chemical Science.
(doi:10.1039/C6SC00011H).
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.
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rvsd MS Lewis Macrocycles Chem Sci .pdf
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Accepted/In Press date: 26 January 2016
e-pub ahead of print date: 27 January 2016
Organisations:
Chemistry
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Local EPrints ID: 391090
URI: http://eprints.soton.ac.uk/id/eprint/391090
ISSN: 1478-6524
PURE UUID: 236222b4-b6f9-43c6-9323-feca47a2a4d5
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Date deposited: 08 Apr 2016 09:04
Last modified: 14 Mar 2024 23:26
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Contributors
Author:
J.E.M Lewis
Author:
R. J. Bordoli
Author:
M. Denis
Author:
C.J. Fletcher
Author:
M. Galli
Author:
E. A. Neal
Author:
E.A. Rochette
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