A Pt(II)-catalyzed [3 + 2] cycloaddition reaction of silyl propadienyl ethers and alkenyl ethers has been developed as the first example of the utilization of allenes as a three-carbon unit in a transition-metal-catalyzed intermolecularcycloaddition reaction. Pt(II)-containing 1,3-dipole equivalents generated by electrophilic activation of silyl propadienyl ethers using a Pt(II) catalyst reacted with