593-77-1Relevant articles and documents
Electrochemical Reductive N-Methylation with CO2Enabled by a Molecular Catalyst
Rooney, Conor L.,Wu, Yueshen,Tao, Zixu,Wang, Hailiang
supporting information, p. 19983 - 19991 (2021/12/01)
The development of benign methylation reactions utilizing CO2 as a one-carbon building block would enable a more sustainable chemical industry. Electrochemical CO2 reduction has been extensively studied, but its application for reductive methylation reactions remains out of the scope of current electrocatalysis. Here, we report the first electrochemical reductive N-methylation reaction with CO2 and demonstrate its compatibility with amines, hydroxylamines, and hydrazine. Catalyzed by cobalt phthalocyanine molecules supported on carbon nanotubes, the N-methylation reaction proceeds in aqueous media via the chemical condensation of an electrophilic carbon intermediate, proposed to be adsorbed or near-electrode formaldehyde formed from the four-electron reduction of CO2, with nucleophilic nitrogenous reactants and subsequent reduction. By comparing various amines, we discover that the nucleophilicity of the amine reactant is a descriptor for the C-N coupling efficacy. We extend the scope of the reaction to be compatible with cheap and abundant nitro-compounds by developing a cascade reduction process in which CO2 and nitro-compounds are reduced concurrently to yield N-methylamines with high monomethylation selectivity via the overall transfer of 12 electrons and 12 protons.
ELECTROREDUCTION OF NITROMETHANE ON HYDROPHOBIZED COPPER ELECTRODES IN A HYDROCHLORIC ACID ELECTROLYTE
Kornienko, G. V.,Kornienko, V. L.
, p. 1590 - 1594 (2007/10/02)
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Mesylhydroxylamines, V. Polysubstituted N-Mesylhydroxylamines
Boldhaus, Michael,Bliefert, Claus,Brink, Klaus,Mattes, Rainer
, p. 1673 - 1674 (2007/10/02)
The preparation and characterization of the following N-mesylhydroxylamines are reported: (CH3SO2)2NOSO2CH3 (1), (CH3SO2)2NOCH3 (2), CH3SO2N(CH3)OSO2CH3 (3), CH3SO2N(H)OCH3 (4), Na(1+)*CH3SO2NOCH3(1-)*1/2H2O (5), CH3SO2N(CH3)OCH3 (6). - Keywords: Methane Sulfonic Acid Derivatives, Hydroxylamines