Electrophilic activation of propargyl silanes has been known to induce the 1,2-silyl shift, generating allylic cations, stabilized by the β-silicon effect. In the absence of reactive nucleophiles silyl dienes as reaction products are obtained. Intramolecular Friedel−Crafts reactions in aryl-substituted propargylic systems, when activated by Brønsted acids, give access to silyl indenes. Herein we investigate the 1,2-silyl shift in propargyl silanes containing an intramolecular nucleophile, derived from the silylated hex-5-yn-1-ol 1, and subsequent cyclization as a novel synthetic approach towards 2-(1-trialkylsilyl)vinyl-substituted heterocycles. This transformation could be induced by addition of various electrophiles (H+, Hal+, RSe+), providing diverse substitution for the C=C bond in the final products. The versatility of this approach has been demonstrated by synthesis various tetrahydrofuran, tetrahydro-2H-pyrane, pyrrolidine and thiolane derivatives.