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Ru‐catalyzed Formation of Thiosilanes and Selenosilanes using Dichalcogenides as a User‐Friendly Alternative to Thiols and Selenols

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The silylation/germylation of several disulfides/diselenides has been established by using commercially available ruthenium catalyst. As a result, several silylthioethers and their germanium and selenium analogs have been synthesized. Notably, the obtained thiosilanes were subsequently utilized in nucleophilic aromatic substitution reaction, leading to unsymmetrical sulfides.


Abstract

A ruthenium-catalyzed reaction for the selective transformation of disulfides (and diselenides) into their silyl (and germyl) counterparts has been developed, as the first example of a thiol/thiolate-free protocol. Our strategy employs commercially available ruthenium dodecacarbonyl as the catalyst in combination with user-friendly hydrosilanes (and hydrogermanes) and odorless dichalcogenides (S, Se). Further derivatization of heteroaryl halides into unsymmetrical sulfides demonstrated the synthetic potential of the obtained silylthioethers.

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