Osawa Ayumi, Uemura Kento, Murakami Shuji, Nakao Yoshiaki
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
Org Lett. 2024 Dec 6;26(48):10218-10223. doi: 10.1021/acs.orglett.4c03526. Epub 2024 Nov 25.
Reductive radical generation has become a cornerstone of modern photoredox chemistry. However, the synthesis of functionalized radical precursors remains a tedious multistep 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.
还原自由基的产生已成为现代光氧化还原化学的基石。然而,功能化自由基前体的合成仍然是一个繁琐的多步过程。在本研究中,我们聚焦于硝基作为氧化还原活性官能团的潜力,并展示了硝基烷烃的脱硝基烯基化反应,该反应由硝基烷烃光还原生成烷基自由基所促进。通过利用硝基烷烃容易进行的α-官能化反应,我们成功地生成了各种功能化的烷基自由基,随后将其用于烯基化反应。