A concise and efficient synthetic strategy to silyl-protected terminal alkynyl sulfides from alkyl or benzyl halides

•We report the synthesis of new intermediate.•The mechanism confirms the synthesis of (Me3Si)3C(S)SLi intermediate.•The temperature does not exceed 0 °C in the synthesis of alkynyl sulfides.

A novel synthetic strategy to silyl-protected terminal alkynyl sulfides via reaction of lithium 2,2,2-tris(trimethylsilyl)ethanedithioate, produced by the reaction of tris(trimethylsilyl)methyllithium with carbon disulfide, and alkyl or benzyl halides has been developed. The scope of the reaction is broad, with a variety of benzylic and aliphatic halides and products were formed in good to excellent yields.

Graphical abstractA novel synthetic strategy to silyl-protected terminal alkynyl sulfides via reaction of lithium 2,2,2-tris(trimethylsilyl)ethanedithioate intermediate with various alkyl or benzyl halides has been developed. This new method has the potential to achieve privileged position as a novel tool for various applications in synthetic chemistry, chemical biology, and material science.Figure optionsDownload full-size imageDownload as PowerPoint slide