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September 10, 2025

A Catalyst-Free Approach to Cyclic Sulfides via Tandem Nucleophilic Substitution and Intramolecular Thiosulfonylation

Puntos clave

The catalyst-free tandem reaction enables the efficient synthesis of cyclic sulfides using bromoalkane-tethered ynones.
This method achieved moderate to good yields in constructing various cyclic thioethers, including rings up to 26 members.
The use of potassium thiosulfonate salts in situ streamlines the preparation process compared to conventional methods.
This mild reaction system demonstrates potential for broad application in thioether synthesis across differing ring sizes.

Resumen

We report an efficient catalyst-free tandem reaction involving nucleophilic substitution and intramolecular thiosulfonylation between bromoalkane-tethered ynones and potassium thiosulfonate salts, yielding cyclic sulfides in moderate to good yields. In contrast to conventional thiosulfonylation methods, this tandem approach eliminates the need for laborious prepreparation of thiosulfonates by employing readily available potassium thiosulfonate salts to generate thiosulfonate precursors in situ. Notably, this mild reaction system has been successfully employed to construct various medium-sized and macrocyclic thioethers, including eight-, nine-, 10-, 13-, 15-, and even 26-membered rings.

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