Abstract
AbstractOxidation of tertiary amines under various conditions generates the corresponding iminium ions, which readily react with the methanenitronate anion, leading to β-nitro amines. Molecular oxygen, peroxides, and peracids are widely used for this purpose in transition-metal-catalyzed reactions. Conversely, organic oxidants such as (diacetoxyiodo)benzene, 2,3-dichloro-5,6-dicyanobenzo-1,4-quinone, and 2,2,6,6-tetramethylpiperidin-1-oxyl are effective without the need for any added catalyst. Visible-light photoinduced coupling reactions are emerging as a safe and environmentally friendly alternative to the above-mentioned procedures. Oxidation is mediated by organometallic complexes of iridium and ruthenium as well as organic sensitizers (rose Bengal and eosin Y) brought into their excited states by irradiation with visible light. Utilization of nitromethyl radicals, obtained by oxidation of nitromethane with ammonium cerium(IV) nitrate, in addition reactions with electron-rich alkenes is limited to the synthesis of nitrosugar derivatives.
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