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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
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.
1478-6524
Lewis, J.E.M
42b46a03-a7ca-4d3a-96e5-a5c962fc9573
Bordoli, R. J.
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Denis, M.
05f9a9b4-df98-4cc8-bebf-33e99bc91e7d
Fletcher, C.J.
4795bfdc-4dcd-4ea6-8590-c93fc71f9815
Galli, M.
5bfc8a21-05e5-4f29-a573-4fa4d7938f7f
Neal, E. A.
72536062-4bc0-49eb-b4e1-a0ce08ddd384
Rochette, E.A.
fbd3ec59-906e-4ea8-8ad7-fe5b820854a4
Goldup, SM.
0a93eedd-98bb-42c1-a963-e2815665e937
Lewis, J.E.M
42b46a03-a7ca-4d3a-96e5-a5c962fc9573
Bordoli, R. J.
f7f925e7-08fc-4b62-97bb-647ecf8b8751
Denis, M.
05f9a9b4-df98-4cc8-bebf-33e99bc91e7d
Fletcher, C.J.
4795bfdc-4dcd-4ea6-8590-c93fc71f9815
Galli, M.
5bfc8a21-05e5-4f29-a573-4fa4d7938f7f
Neal, E. A.
72536062-4bc0-49eb-b4e1-a0ce08ddd384
Rochette, E.A.
fbd3ec59-906e-4ea8-8ad7-fe5b820854a4
Goldup, SM.
0a93eedd-98bb-42c1-a963-e2815665e937

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).

Record type: Article

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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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
ORCID for SM. Goldup: ORCID iD orcid.org/0000-0003-3781-0464

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Date deposited: 08 Apr 2016 09:04
Last modified: 17 Dec 2019 01:34

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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
Author: SM. Goldup ORCID iD

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