Towards a Robust and Reliable Method for the Reduction of Functionalized Sulfoxides

Abstract

Several functionalized sulfoxides in the modafinil series, which bear another reducible function, were chemoselectively reduced to thioethers using the KI/AcCl system.

Indium‐Catalyzed Deoxygenation of Sulfoxides with Hydrosilanes

“…Hence, the combination of a hydrosilane and a solvent in the presence of the modest Lewis acid, InBr 3 , was re-examined. First, when alkoxysilanes, such as triethoxysilane, polymethyl-hydrosiloxane (PMHS), and tetramethyldisiloxane (TMDS) were used, the first two alkoxysilanes did not undertake the desired deoxygenation, but the latter one showed a positive effect to some extent (entries [10][11][12]. An arylsilane, PhSiH 3 , that has previously shown a better performance in related studies on the reduction of sulfoxides consumed 39% of sulfoxide 1 a (entry 13).…”