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.