Transition Metal-Free Intermolecular alpha-C-H Amination of Ethers at Room Temperature

We describe a new method for the intermolecular amination of the alpha-C-H bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti-cancer prodrug Tegafur and its analogues.