Remote C(sp3)–H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
2017-01-17T20:35:14Z (GMT) by
This letter describes the development of a method for selective remote C(sp3)–H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)–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 °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(sp3)–H bonds, including 3°, 2°, and benzylic C–H sites in primary, secondary, and tertiary amine substrates.
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