Molecule of the Month
August 2024
Mechanochemistry Facilitates Nitrative Difunctionalization via Radical Ligand Transfer and Electron Catalysis

A general protocol is reported for olefin difunctionalization via mechanochemistry, using cooperative radical ligand transfer (RLT) and electron catalysis. Employing mechanochemical force and catalytic TEMPO, ferric nitrate utilizes nitryl radicals to transfer nitrooxy groups via RLT and mediate electron catalysis at room temperature.
A range of alkenes exhibited chemo- and regioselective 1,2-nitronitrooxylation under solvent-free conditions with excellent functional group tolerance. Mechanistic studies highlighted the significant impact of mechanochemistry and the radical nature of this process.

This work was carried out in the group of Prof. Dr. Dmitry Katayev.

References:

  • S. Patra, V. Valsamidou, B. N. Nandasana, D. Katayev;
    "Mechanochemistry Drives Alkene Difunctionalization via Radical Ligand Transfer and Electron Catalysis"
    Adv. Sci., 2024, in press; doi:10.1002/advs.202402970.