10.1021/acs.orglett.6b03731.s002 Melissa Lee Melissa Lee Melanie S. Sanford Melanie S. Sanford Remote C(sp<sup>3</sup>)–H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate American Chemical Society 2017 transition metal catalyst protonated aliphatic amines method amine substrates Protonated Aliphatic Amines bond 2017-01-17 20:35:11 Journal contribution https://acs.figshare.com/articles/journal_contribution/Remote_C_sp_sup_3_sup_H_Oxygenation_of_Protonated_Aliphatic_Amines_with_Potassium_Persulfate/4558555 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.