Allenes are important functional groups especially in synthetic organic chemistry. Due to their unique reactivity and high level of chirality transfer, allenes can be used as building blocks in the synthesis of complex molecules. In recent decades transition-metal catalyzed synthesis of allenes with organometallic reagents has become attractive method. For the synthesis of functionalized allenes, addition of different nucleophiles with the help of various transition metals to propargylic compounds bearing a leaving group has been mostly used. Transition metals are crucial for these reactions for shifting them from SN2 to SN2’ for the formation of allenes. Within the context of this research, a novel palladium-catalyzed arylation reactions of (Z)-2,4-enyne oxiranes with organoborons have been investigated. As a result of the 1,5-substitution reaction, aryl-substituted vinylallenes bearing a hydroxyl group on the allylic position (7-aryl-3,5,6-trien-2-ol) were obtained in high yields and diastereoselectivities. We were able to also disclose that Diels-Alder adducts could be obtained with excellent endo and facial selectivities when the vinylallen types of this study were reacted with dienophiles.