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

Ling Zhou; Cassandra G. Freyschlag; Bingjun Xu; Cynthia M. Friend; Robert J. Madix

doi:10.1039/B921066K

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

Ling Zhou,^a Cassandra G. Freyschlag,^a Bingjun Xu,^b Cynthia M. Friend^ab and Robert J. Madix*^a

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* Corresponding authors

^a School of Engineering and Applied Sciences, Harvard University, 29 Oxford Street, Cambridge, USA
E-mail: rmadix@seas.harvard.edu
Fax: +1 617 496 8410

^b Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, USA

Abstract

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 β-H elimination from the adsorbed hemiaminal.

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Supplementary files

Experimental details, identification of N, N-dimethylformamide in reactions (Table S1), reaction of d ₆-dimethylamine with d ₁-formate on O/Ag(111) (Fig. S1), oxidation of dimethylamine (Fig. S2) and formaldehyde (Fig. S3) on 0.1 ML O/Ag(110) PDF (1464K)

Article information

DOI: https://doi.org/10.1039/B921066K
Article type: Communication
Submitted: 08 Oct 2009
Accepted: 07 Dec 2009
First published: 21 Dec 2009

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Chem. Commun., 2010,46, 704-706

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

L. Zhou, C. G. Freyschlag, B. Xu, C. M. Friend and R. J. Madix, Chem. Commun., 2010, 46, 704 DOI: 10.1039/B921066K

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Chemical Communications

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

Abstract

Supplementary files

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

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