Photoinduced formation of cubyl aryl thioethers and synthesis of monocubyl analogue of dapsone
Photoinduced formation of cubyl aryl thioethers and synthesis of monocubyl analogue of dapsone
1,4-Disubstituted cubyl aryl thioethers were generated from the corresponding iodocubanes and aryl thiolates upon UV irradiation in dimethyl sulfoxide at room temperature. This simple procedure was found to be compatible with a variety of substituted aryl thiolates. This finding paved the way to a synthesis of the monocubyl analogue of dapsone, a key molecule in the treatment of leprosy, also known as Hansen’s disease, and of acne.
8580-8584
Donnier-Valentin, Laly
68ec68c0-2382-475d-bd2f-86ed83afbf3d
Kassamba, Seydou
893e3147-5429-4553-b9f8-543346b24403
Legros, Julien
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Fressigné, Catherine
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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
8 December 2023
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)
Photoinduced formation of cubyl aryl thioethers and synthesis of monocubyl analogue of dapsone.
Organic Letters, 25 (48), .
(doi:10.1021/acs.orglett.3c03372).
Abstract
1,4-Disubstituted cubyl aryl thioethers were generated from the corresponding iodocubanes and aryl thiolates upon UV irradiation in dimethyl sulfoxide at room temperature. This simple procedure was found to be compatible with a variety of substituted aryl thiolates. This finding paved the way to a synthesis of the monocubyl 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
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Accepted/In Press date: 17 November 2023
e-pub ahead of print date: 21 November 2023
Published date: 8 December 2023
Additional Information:
Funding Information:
This work has also been partially supported by University of Rouen Normandy, INSA Rouen Normandy, the Centre National de la Recherche Scientifique (CNRS), Labex SynOrg (ANR-11-LABX-0029), Carnot Institute I2C, the graduate school for research XL-Chem (ANR-18-EURE-0020 XL CHEM), and by Région Normandie.
Identifiers
Local EPrints ID: 486081
URI: http://eprints.soton.ac.uk/id/eprint/486081
ISSN: 1523-7060
PURE UUID: a53a119f-4148-4dcf-85ec-e030fcc7f5b3
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Date deposited: 09 Jan 2024 17:32
Last modified: 18 Mar 2024 02:52
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Contributors
Author:
Laly Donnier-Valentin
Author:
Seydou Kassamba
Author:
Julien Legros
Author:
Catherine Fressigné
Author:
Daniela Vuluga
Author:
Michaël De Paolis
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