Synthesis of cyclic organosilicon compounds by palladium-catalyzed reactions of 2-silylaryl triflates

Abstract

2-Silylaryl triflates are widely employed as effective aryne precursors in organic synthesis, but their use as substrates for the synthesis of organosilicon compounds by retaining their silicon substituents is another attractive usage of these reagents. In particular, cyclic compounds having a silicon atom in the ring are promising candidates for various biologically active substances and optoelectronic functional materials. In this context, new synthetic methods of silicon-containing cyclic compounds have been actively investigated through the development of palladium-catalyzed reactions of 2-silylaryl triflates without generating aryne intermediates. As a result, selective synthesis of various silacyclic compounds has been achieved via C–H and/or C–Si bond activations as well as intramolecular exchange between these bonds and C–Pd bonds that are formed as reaction intermediates. An overview of this topic is described including the mechanistic insights.