In this work we continue our studies on the broad possibilities for propargyl silane functionalization, offered by electrophile induced 1,2-silyl migration.1 Herein we investigate the use of hypervalent iodine (III) reagents as formal carbon electrophiles to activate the propargyl silane moiety (Scheme 1). Copper (I) reacts with diaryliodonium salts to generate the highly electrophilic Ar-CuIII species, which activates the propargyl silane to undergo the 1,2-silyl shift, forming an allyl cation intermediate. In the absence of an internal nucleophile, dienes are obtained, whereas present C- or heteroatom nucleophiles provide indenes or heterocycles, respectively. A variety of aromatic groups with electron donating and electron withdrawing substituents are applicable in this reaction, as well as some heteroaromatic groups.