Organocatalytic Aerobic Oxidative Monodealkylation of tert-Amines to sec-Amines

The highly efficient monodealkylation of tertiary amines was achieved using hydroxylamine and NOx catalysts under mildly aerobic conditions. This approach demonstrates high functional group tolerance and a broad substrate scope, including amino acids and alkaloids with complex structures. Mechanistic studies have suggested that the reaction proceeds via aminium radical cations via the one-electron oxidation of tertiary amines.