An efficient procedure for the copper-catalyzed cross-coupling between a broad range of cyanamides and iodoalkenes is reported. Upon reaction with catalytic amounts of copper(I) iodide and 2,2'-bisimidazole in the presence of cesium carbonate in DMF at 80 °C, a fast, regioselective, and stereoretentive cross-coupling occurs. This reaction, which was found to have a broad substrate scope, provides the first general entry to N-alkenylcyanamides, building blocks that hold great synthetic potential.