Recent Advances in Free Radical Reactions of <i>gem</i> -Bromonitroalkanes

Nitro compounds are important precursors and intermediates for synthesizing pharmaceuticals, agrochemicals, dyes, and explosives, which necessitates the development of novel methods for their synthesis and functionalization. While the spin-paired chemistry of the nitroalkanes has been extensively studied, their radical reactivity is relatively underexplored. Notably, <i>gem</i>-bromonitroalkanes (BNAs) offer a convenient route to electron-deficient α-nitro radicals, which display umpoled electronics, and thus selectivity, compared to majority of the reported radical reactions. This underscores the importance of compiling and analyzing reactions involving this moiety. Therefore, we present our perspective on the free-radical reactivity of BNAs, with a focus on elucidating the mechanistic underpinnings to encourage their wider adoption within the synthetic organic community.