Silylative dearomatizations of indole-2-carboxylates were accomplished using a copper(I) catalyst and silylboronates. This reaction presumably proceeds through regioselective addition of silylcopper(I) species to indole substrates followed by highly diastereoselective protonation of the resulting copper(I) enolate intermediates to afford the corresponding dearomative silylation products. The first silylative dearomatization of pyrroles using the developed catalytic system is also described.