Iron(II, III)-catalyzed oxidative N-dealkylation of amines with dioxygen

Add time:08/06/2019    Source:sciencedirect.com

Labile iron complexes (e.g., [FeIII(bpy)2]MeCN3+, [FeII(bpy)2]MeCN2+, [FeIII(H2O)6]MeCN3+, and [FeII(H2O)6]MeCN2+) in base-free acetonitrile activate dioxygen for the direct oxygenation of N,N- and N-alkylated amines to form N-dealkylated products and corresponding aldehydes. N,N-dimethylaniline (DMA) is oxidized to N-methylaniline (MA) and formaldehyde as well as to N-methylanilide. Formaldehyde and the excess of substrate undergo condensation reaction to produce 4,4′-methylenebis(N,N-dimethylaniline) (MBDME). Small amounts of N-methylformanilide (MF) and formanilide are also formed during oxidation of N,N-dimethylaniline and N-methylaniline respectively. Iron(III) catalysts are reduced by the substrate to iron(II), which activates dioxygen. Dioxygen activation step is preceded by the equilibrium reaction between iron(II) catalyst and substrate.

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