Journal of the American Chemical Society, Vol.137, No.46, 14590-14593, 2015
Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules
Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Bronsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp(3))-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.