Journal of the American Chemical Society, Vol.134, No.17, 7242-7245, 2012
Iodine(III)-Mediated Intermolecular Allylic Amination under Metal-Free Conditions
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.