Direct selective oxygen-assisted acylation of amines driven by metallic silver surfaces: dimethylamine with formaldehyde

Facile, direct acylation of dimethylamine with formaldehyde to N,N-dimethylformamide proceeds with a selectivity approaching 100% at low oxygen concentrations on metallic silver surfaces; the reaction proceeds via nucleophilic attack of adsorbed dimethylamide on formaldehyde with subsequent beta-H e...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2010-01, Vol.46 (5), p.704-706
Main Authors: Zhou, Ling, Freyschlag, Cassandra G, Xu, Bingjun, Friend, Cynthia M, Madix, Robert J
Format: Article
Language:English
Subjects:
Acylation
Amines
Chemical attack
Dimethylamines - chemistry
Dimethylformamide
Formaldehyde
Formaldehyde - chemistry
Formamides - chemical synthesis
Formamides - chemistry
Molecular Structure
Oxygen - chemistry
Selectivity
Silver
Silver - chemistry
Surface Properties
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Summary:Facile, direct acylation of dimethylamine with formaldehyde to N,N-dimethylformamide proceeds with a selectivity approaching 100% at low oxygen concentrations on metallic silver surfaces; the reaction proceeds via nucleophilic attack of adsorbed dimethylamide on formaldehyde with subsequent beta-H elimination from the adsorbed hemiaminal.
ISSN:1359-7345
1364-548X
DOI:10.1039/b921066k