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 elimination from the adsorbed hemiaminal.
Zhou
Ling
L
School of Engineering and Applied Sciences, Harvard University, 29 Oxford Street, Cambridge, MA 02138, USA.
Freyschlag
Cassandra G
CG
Xu
Bingjun
B
Friend
Cynthia M
CM
Madix
Robert J
RJ
D000215:Acylation; D004123:Dimethylamines / Q000737:chemistry*; D004126:Dimethylformamide; D005557:Formaldehyde / Q000737:chemistry*; D005559:Formamides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013499:Surface Properties
D004123:Dimethylamines; D005559:Formamides; D005557:Formaldehyde; D012834:Silver; D004126:Dimethylformamide; C034516:dimethylamine; D010100:Oxygen