Catalytic Aerobic Carbooximation of Alkenes Using Secondary Nitroalkanes as Both α‑Nitro Alkyl Radical and Nitrogen Monoxide Sources

Aerobic nitro-nitrite isomerization of secondary nitroalkanes
is
postulated to proceed via the intermediacy of the α-nitro alkyl
radical, where the corresponding Nef-type products, ketones, and nitrogen
monoxide can be obtained as byproducts. To explore the catalytic aerobic
carbooximation of alkenes using secondary nitroalkanes, phase-transfer
catalysis of KSeCN and TBAI has been developed. The current aerobic
carbooximation of alkenes utilizes nitroalkanes as both radical and
nitrogen monoxide sources in water without external oxidants and prefunctionalized
nitroalkanes.