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

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posted on 2017-01-17, 20:35 authored by Melissa Lee, Melanie S. Sanford
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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