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.

Automated summary

This novel method utilizes N-hydroxyphthalimide and its analogues as transient nitroxyl-radical precursors and TEMPO+BF4- as both the oxidant and source of persistent nitroxide to achieve regioselective vicinal dioxidation of alkenes under transition metal and organic peroxide free conditions. It efficiently synthesizes structurally important dioxidation products from simple alkenes and complex bioactive molecule derivatives.