%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