Aerobic Metal-Free Dioxygenation of Alkenes with tert-Butyl Nitrite and N‑Hydroxylamines

Metal-free dioxygenation of alkenes with tert-butyl nitrite and N-hydroxylamines (N-hydroxyphthalimide, N-hydroxybenzotriazole, and N-hydroxysuccinimide) is described to produce β-aminoxy nitrate esters using air as the oxidant. These organic nitrates can be readily converted into 1,2-diols and 1,2-diketone with broad substrate scope and functional group diversity.