Transition-metal-catalyzed Si-H bond insertion reactions are generally limited to stabilized diazo compounds. An efficient copper-catalyzed Si-H bond insertion reaction of N-propargyl ynamides with hydrosilanes is described, allowing practical and atom-economic construction of valuable organosilanes in generally moderate to excellent yields under mild reaction conditions. Notably, this reaction constitutes a new method of Si-H bond insertion reaction involving vinyl cations as key intermediates.