Reductive radical generation has become a cornerstone of modern photoredox chemistry. However, the synthesis of functionalized radical precursors remains a tedious multi-step process. In this study, we focus on the potential of the nitro group as a redox-active functional group and present denitrative alkenylation of nitroalkanes, facilitated by photoreductive generation of alkyl radicals from nitroalkanes. By taking advantage of the facile α-functionalization of nitroalkanes, we successfully generate various functionalized alkyl radicals, which are subsequently used in the alkenylation reactions.