Ionic Liquids-Assisted Ring Opening of Three-Membered Heterocycles with Thio- and Seleno-Silanes

Abstract

Ring opening reactions of strained heterocycles (epoxides, aziridines, thiiranes) by silyl chalcogenides, such as thiosilanes and selenosilanes, can be efficiently performed in a variety of ionic liquids, which can behave as reaction media and in some cases also as catalysts. This protocol enables an alternative access to β-functionalized sulfides and selenides under mild conditions.

Cyano(fluoro)borate and cyano(hydrido)borate ionic liquids: low-viscosity ionic media for electrochemical applications

“…The equilibrium presented in Scheme 2 has been proposed as explanation for the Brønsted acid catalytic activity of imidazolium ILs with the anions [BF 4 ] − and [PF 6 ] − . 107 Alternatively, a hopping mechanism of fluoride anions in [EMIm][BF 4 ], which agrees to the relatively low Lewis acidity of boron trifluoride, 108 may rationalize the relatively high ionicity and high conductivity ( σ and Λ imp ) of [EMIm][BF 4 ] (Scheme 2).…”