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 Brønsted acid (HBF4) or an aza­philic Lewis acid (BF3) to enable remote, non-directed C­(sp3)–H oxid­ations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxid­ation and promote remote functionalization.