Remote C(sp<sup>3</sup>)–H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate

2017-01-17T20:35:11Z (GMT) by Melissa Lee Melanie S. Sanford
This letter describes the development of a method for selective remote C­(sp<sup>3</sup>)–H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C­(sp<sup>3</sup>)–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(sp<sup>3</sup>)–H bonds, including 3°, 2°, and benzylic C–H sites in primary, secondary, and tertiary amine substrates.