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A Cu‐catalyzed vinylation method for alkenyl ethers has been developed. In this strategy, both chain and cyclic alkenyl ether substrates were applicable, and the target products were obtained in up to 95% yields and with the E/Z selectivities of >98:2. Furthermore, we have successfully applied this method to directly vinylate the C‐2 position of protected glucals, offering a valuable tool for their functionalization. Moreover, through the utilization of alkenyl alcohols as substrates, we accomplished a 1,2‐alkenyloxylation of alkenyl double bond, enabling the synthesis of functionalized cyclic ether compounds with five or six‐membered rings.