title: Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate.
abstract: 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.
authors.affiliation: University of Michigan , Department of Chemistry, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
authors.forename: Melissa
authors.initials: M
authors.lastname: Lee
authors.affiliation: University of Michigan , Department of Chemistry, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
authors.forename: Melanie S
authors.identifier: 0000-0001-9342-9436
authors.initials: MS
authors.lastname: Sanford
mesh_terms: D000588:Amines / Q000737:chemistry*; D015394:Molecular Structure; D017680:Potassium Compounds; D013431:Sulfates
chemical_list: D000588:Amines; D017680:Potassium Compounds; D013431:Sulfates; C009007:potassium persulfate