Oxoammonium Salt-Mediated Regioselective Vicinal Dioxidation of Alkenes: Relying on Transient and Persistent Nitroxides.

A novel, easy-to-handle, and regioselective vicinal dioxidation of alkenes under transition metal and organic peroxide free conditions has been developed. This approach uses N-hydroxyphthalimide and its analogues as the transient nitroxyl-radical precursors and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO+BF4-) as the oxidant as well as the source of persistent nitroxide. By employing this method, multifarious structurally important dioxidation products were efficiently synthesized from simple alkenes and complex bioactive molecule derivatives.