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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
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. We demonstrate the first electrochemical functionalisation of cubane by oxidative decarboxylative ether formation (Hofer‐Moest reaction). 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
0947-6539
374-378
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
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), 374-378. (doi:10.1002/chem.201904479).

Record type: Article

Abstract

The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. We demonstrate the first electrochemical functionalisation of cubane by oxidative decarboxylative ether formation (Hofer‐Moest reaction). The mild conditions are compatible with the presence of other oxidisable functional groups, and the use of flow electrochemical conditions allows straightforward upscaling.

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Manuscript chem201904479 - Accepted Manuscript
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Accepted/In Press date: 1 October 2019
e-pub ahead of print date: 8 October 2019
Published date: 7 January 2020
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
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 28 Oct 2019 17:30
Last modified: 18 Feb 2021 16:55

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