Useful Application of Thiosilanes for Preparation of Symmetrical and Unsymmetrical Dialkyl Sulfides

Thiosilanes are of major interest in synthetic utility since they can be converted into sulfides by simple reaction sequence. Abel and co-workers found that alkylthiosilanes reacted with alkyl halides to give the corresponding halogenosilanes and dialkyl sulfides.1 However, the reaction has to be done under the very drastic conditions (e. g. reaction temperature; 160–180°C, reaction time; 15hr-4weeks), and halogenosilanes must be continuously removed from the reaction system to obtain alkyl sulfides, and also the product yields are very low (31–68%). Here, we wish to report that ethylthiotrimethylsilane (Me3SiSEt)1, hexamethyldisilthiane [(Me3Si)2S]2, and bifunctional thiosilane [Me3 SiS(CH2)4SSiMe3]2, react with various primary alkyl halides in the presence of sodium methoxide in THF at room temperature to give the corresponding symmetrical and unsymmetrical sulfides in excellent yields.2