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 s...

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Veröffentlicht in:Organic letters 2023-12, Vol.25 (48), p.8580-8584
Hauptverfasser: Donnier-Valentin, Laly, Kassamba, Seydou, Legros, Julien, Fressigné, Catherine, Vuluga, Daniela, Brown, Richard C D, Linclau, Bruno, De Paolis, Michaël
Format: Artikel
Sprache:eng
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Chemical Sciences
Organic chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03372