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.