Following our previous studies on propargyl silane functionalization,1 we now explore the arylation of propargyl silanes 1, using iodanes as formal carbon electrophiles. In the absence of a propargylic silyl group, transition metal-catalyzed (Cu, Pd) approaches typically result in terminal alkyne C(sp)–H arylation.2 In contrast, propargyl silanes, depending on C-skeleton length, undergo either 1,3- or 1,1carbodifunctionalization (Scheme 1). In substrates containing an internal nucleophile, this leads to the formation of 5-membered heterocycles 4, containing a styryl side chain, or 6-membered heterocycles 5. In the case of aliphatic propargyl silanes, an arylation - β-H elimination event occurs, leading to aryl dienes 2 and indenes 3. The introduction of a variety of (hetero)aromatic groups with electron-donating and electron-withdrawing substituents was studied for this reaction.