An aerobic carboheterocyclization of functionalized alkenes has been developed using secondary nitroalkanes as dual sources of α-nitroalkyl radicals and nitric oxide (NO) under cooperative phase transfer catalysis of KSeCN and TBAI. This method enables efficient synthesis of nitrogen- and oxygen-containing heterocycles via radical redox interplay between nitric oxide and tertiary carbon radicals. The current study highlights the mechanistic role of aerobic nitro-nitrite isomerization and expands the synthetic utility of radical-mediated tandem cyclizations under aerobic conditions.
Chowdhury et al. (Wed,) studied this question.