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Photo-induced formation of cubyl arylthioethers, synthesis of mono cubyl analogue of dapsone

Photo-induced formation of cubyl arylthioethers, synthesis of mono cubyl analogue of dapsone
Photo-induced formation of cubyl arylthioethers, synthesis of mono cubyl analogue of dapsone
1,4-Disubstituted cubyl arylthioethers were generated from the corresponding iodocubanes and aryl thiolates upon UV-irradiation in dimethylsulfoxide at room temperature. This simple procedure was found compatible with a variety of substituted aryl thiolates substituted. This finding paved the way to a synthesis of the mono cubyl analogue of dapsone, a key molecule in the treatment of leprosy, also known as Hansen’s disease, and of acne.
1523-7060
Donnier-Valentin, Laly
68ec68c0-2382-475d-bd2f-86ed83afbf3d
Kassamba, Seydou
893e3147-5429-4553-b9f8-543346b24403
Legros, Julien
0ad85dc7-e84f-4c8c-95a4-2aa46fbe89ec
Fressigné, Catherine
079ecc54-094c-4448-948d-5f4c4f01cd14
Vuluga, Daniela
261e6c4f-f477-4829-b6df-1fb757f75553
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
De Paolis, Michaël
53524a22-e46d-4411-8e9d-1ea9d220d784
Donnier-Valentin, Laly
68ec68c0-2382-475d-bd2f-86ed83afbf3d
Kassamba, Seydou
893e3147-5429-4553-b9f8-543346b24403
Legros, Julien
0ad85dc7-e84f-4c8c-95a4-2aa46fbe89ec
Fressigné, Catherine
079ecc54-094c-4448-948d-5f4c4f01cd14
Vuluga, Daniela
261e6c4f-f477-4829-b6df-1fb757f75553
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
De Paolis, Michaël
53524a22-e46d-4411-8e9d-1ea9d220d784

Donnier-Valentin, Laly, Kassamba, Seydou, Legros, Julien, Fressigné, Catherine, Vuluga, Daniela, Brown, Richard C.D., Linclau, Bruno and De Paolis, Michaël (2023) Photo-induced formation of cubyl arylthioethers, synthesis of mono cubyl analogue of dapsone. Organic Letters. (In Press)

Record type: Article

Abstract

1,4-Disubstituted cubyl arylthioethers were generated from the corresponding iodocubanes and aryl thiolates upon UV-irradiation in dimethylsulfoxide at room temperature. This simple procedure was found compatible with a variety of substituted aryl thiolates substituted. This finding paved the way to a synthesis of the mono cubyl analogue of dapsone, a key molecule in the treatment of leprosy, also known as Hansen’s disease, and of acne.

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thiocubanes_1511 - Accepted Manuscript
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Accepted/In Press date: 17 November 2023
Additional Information: We are very grateful to the ANR (CERES, ANR-21-CE07-0048)) for a fellowship to L. D-V. and S. K. We acknowledge the financial support from ISCE-CHEM (Interreg IV, European Program), Interreg FCE LabFact (European Program and co-funded by ERDF) and Labex SynOrg (ANR-11-LABX-0029).
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Identifiers

Local EPrints ID: 484734
URI: http://eprints.soton.ac.uk/id/eprint/484734
ISSN: 1523-7060
PURE UUID: bbb35a39-a888-44b0-b5b0-a1301867d8a8
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 20 Nov 2023 17:54
Last modified: 17 Nov 2024 05:01

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Contributors

Author: Laly Donnier-Valentin
Author: Seydou Kassamba
Author: Julien Legros
Author: Catherine Fressigné
Author: Daniela Vuluga
Author: Richard C.D. Brown ORCID iD
Author: Bruno Linclau ORCID iD
Author: Michaël De Paolis

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