%0 Journal Article %A Lee, Melissa %A Sanford, Melanie S. %D 2017 %T Remote C(sp3)–H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate %U https://acs.figshare.com/articles/journal_contribution/Remote_C_sp_sup_3_sup_H_Oxygenation_of_Protonated_Aliphatic_Amines_with_Potassium_Persulfate/4558555 %R 10.1021/acs.orglett.6b03731.s002 %2 https://ndownloader.figshare.com/files/7383547 %K transition metal catalyst %K protonated aliphatic amines %K method %K amine substrates %K Protonated Aliphatic Amines %K bond %X 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. %I ACS Publications