A new approach to direct intermolecular allylic amination has been developed using metal-free conditions at room temperature. The reaction employs a hypervalent iodine(III) reagent as an oxidant and bistosylimide as a nitrogen source. A series of different allylic aminations are presented with up to a 99% yield. Mechanistic studies including isotope labeling and Hammett correlation suggest that depending on the substrate structure two different mechanisms can be operating.
![Iodine(III)-mediated intermolecular allylic amination under metal-free conditions](https://www.iciq.org/wp-content/uploads/2014/03/IodineIII-mediated_7242.gif)