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.二级硝基烷烃的需氧硝基-亚硝酸酯异构化反应，被推测经由α-硝基烷基自由基中间体进行，副产物可获得相应的内夫（Nef）型产物、酮类与一氧化氮。为探索以二级硝基烷烃为底物的烯烃催化需氧碳肟化反应，本研究开发了硒氰酸钾（KSeCN）与四丁基碘化铵（TBAI）参与的相转移催化体系。当前该烯烃需氧碳肟化反应以硝基烷烃同时作为自由基源与一氧化氮源，在水相体系中进行，且无需外加氧化剂与预官能化硝基烷烃。