Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate

This letter describes the development of a method for selective remote C(sp(3))-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp(3)) H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 degrees C with amine as limiting reagent) and do not require a transition metal.catalyst. This method is applicable to a variety of types of C(sp(3)) H bonds, including 3 degrees, 2 degrees, and benzylic C-H sites in primary,) secondary, and tertiary amine substrates.