Recent Applications of Hexamethyldisilathiane (TMS2S) in Organic Synthesis

[摘要] Hexamethyldisilathiane (TMS2S), also namedbis(trimethylsilyl) sulfide, (CAS: 3385-94-2), was reportedfor the first time in the early 1950’s.1 This liquid compound(bp 160 °C) was prepared by the reaction between iodotrimethylsilane and silver sulfide. Alternatively,bis(trimethylsilyl) sulfide has been also prepared by the addition of disodium sulfide on chlorotrimethylsilane.1,2TMS2S is nowadays commercially available (ca. 28 €/g).3This reagent can be viewed as a S1 source of sulfide that isless toxic, less flammable, and easier to handle than gaseoushydrogen sulfide (H2S). On contact with water, TMS2S releases H2S and should be stored in a cold and dry place in anoxygen-free atmosphere. TMS2S is used as a sulfur transferagent for the synthesis of alkyl sulfides, thioaldehydes, orthioketones but also as a reducing agent.4 TMS2S is also employed in the synthesis of inorganic–organic hybrid clusters5 or phosphinidene sulfide compounds.6 It is noteworthy that the number of publications describing the use ofTMS2S has steadily increased since the 1950’s to reach anaverage of 65 publications per year from 2015 to 2022.7This Spotlight article highlights the versatility of TMS2S as aS1 source of sulfides and its recent applications in organicsynthesis.

[学科分类] 精神健康和精神病学

[关键词] hexamethyldisilathiane;bis(trimethylsilyl) sulfide;S1 source