Keywords: Homogenous catalysis / Domino reactions / Palladium catalysis / Carbooligocyclization / DienyneThe cascade reaction modes and hence the outcomes of the palladium-catalyzed oligocyclizations of various 2-bromoalka-1,(n+m+1)-diene-(n+1)-yne substrates were found to be highly dependent on the tether lengths between the multiple bond fragments, and on the nature of the substituent at the non-brominated vinylic terminus. Just like 2-bromododeca-1,11-dien-6-ynes with their two three-atom tethers, 2-bromotrideca-1,12-dien-7-ynes 8 and 2-bromotetradeca-1,13-dien-8-ynes 17, with combinations of four-and three-as well as five-and three-atom tethers, under Heck-type reaction conditions undergo, after the initial oxidative addition step, two consecutive n-exo-dig and m-exo-trig carbopalladations followed by β-hydride elimination and ensuing 6π-electro-