Silicon-Assisted Synthesis and Functionalization of Sulfurated and Selenated Compounds

GRAPHICAL ABSTRACT

Abstract

The synthetic potential of thiosilanes and selenosilanes toward various electrophiles is described, focusing on the synthesis of a representative range of thiocarbonyl, selenocarbonyl, β-functionalized compounds, and acyl-seleno derivatives. Reactions of silyl chalcogenides with epoxides, episulfides, and aziridines allowed the synthesis of β-hydroxy, β-mercapto, and β-amino thiols, as well as of β-substituted selenides and diselenides. A peculiar behavior was observed in the reaction with episulfides, leading to seven-membered trithia- and dithiaseleno-heterocycles. Furthermore, carbodesilylation of α-heterosubstituted organosilanes provided a smooth access to benzothiophene and benzofuran-derivatives.

Keywords:

• Thiosilanes
• selenosilanes
• strained ring systems
• fluoride ion
• regioselectivity