Nitro Compounds in Cascade Reactions

• Applicant: Professorin Dr. Meike Niggemann
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2019 to 2023
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 425493558

Cascade reactions are a highly efficient tool for synthetic organic chemistry. Nitro compounds should be an ideal starting material for these reactions. The high oxidation state of the nitrogen atom allows for a stepwise reduction. Thereby, intermediates are successively generated that can be used as reagents for the synthesis of functionalized amines. Despite the obvious advantages, such a reaction sequence remains largely underdeveloped, and only a few methods were recently reported, that realize a direct transformation of nitro compounds without the detour to the fully reduced amine. Thus, potential applications for the reactivity of the oxidized N-atom in nitro groups remain unexplored. On the way towards a general concept for nitro compounds in cascade reactions, we already developed a novel, B2Pin2-mediated reduction process that allows for a nitro-nitrenoid-aminoborane-amine-sequence. Diverse and interesting reactivity can be expected from the two key intermediates of this transformation, the nitrenoid and the aminoborane. Hence, this new sequence provides a versatile blueprint for the development of further cascade reactions.

• DFG Programme: Research Grants