Remote C(sp<sup>3</sup>)–H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
2017-01-17T20:35:11Z (GMT) by
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.
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