Cubane electrochemistry: direct conversion of cubane carboxylic acids to alkoxy cubanes using the Hofer-Moest reaction under flow conditions
Cubane electrochemistry: direct conversion of cubane carboxylic acids to alkoxy cubanes using the Hofer-Moest reaction under flow conditions
The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. The first electrochemical functionalisation of cubane by oxidative decarboxylative ether formation (Hofer–Moest reaction) was demonstrated. The mild conditions are compatible with the presence of other oxidisable functional groups, and the use of flow electrochemical conditions allows straightforward upscaling.
bioisostere, cubanes, electrosynthesis, flow electrochemistry, oxidative decarboxylation
374-378
Collin, Diego, Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Folgueiras Amador, Ana
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Pletcher, Derek
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
7 January 2020
Collin, Diego, Edgard
d0d4eecb-1e37-4bfe-ae07-351434d2f227
Folgueiras Amador, Ana
080c345d-0a05-406a-bf7c-1939ca9c0aaa
Pletcher, Derek
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Collin, Diego, Edgard, Folgueiras Amador, Ana, Pletcher, Derek, Light, Mark, Linclau, Bruno and Brown, Richard C.D.
(2020)
Cubane electrochemistry: direct conversion of cubane carboxylic acids to alkoxy cubanes using the Hofer-Moest reaction under flow conditions.
Chemistry - A European Journal, 26 (2), .
(doi:10.1002/chem.201904479).
Abstract
The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. The first electrochemical functionalisation of cubane by oxidative decarboxylative ether formation (Hofer–Moest reaction) was demonstrated. The mild conditions are compatible with the presence of other oxidisable functional groups, and the use of flow electrochemical conditions allows straightforward upscaling.
Text
Manuscript chem201904479
- Accepted Manuscript
More information
Accepted/In Press date: 1 October 2019
e-pub ahead of print date: 8 October 2019
Published date: 7 January 2020
Additional Information:
Funding Information:
The authors acknowledge financial support from the ERDF (LabFact: InterReg V project 121) and EPSRC (Photo-Electro Programme Grant EP/P013341/1 and EP/K039466/1).
Publisher Copyright:
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Keywords:
bioisostere, cubanes, electrosynthesis, flow electrochemistry, oxidative decarboxylation
Identifiers
Local EPrints ID: 435238
URI: http://eprints.soton.ac.uk/id/eprint/435238
ISSN: 0947-6539
PURE UUID: 5f47aa8b-20db-46c3-8ffe-bb891ea9c802
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Date deposited: 28 Oct 2019 17:30
Last modified: 17 Mar 2024 02:51
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Contributors
Author:
Diego, Edgard Collin
Author:
Ana Folgueiras Amador
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