Abstract
The first solvent and catalyst free three-component coupling
of carbonyl compounds, amines and triethylphosphite is achieved
producing α-aminophosphonates at ambient temperature in
very high yields.
Key words
three-component coupling - carbonyl compounds - amines - triethyl phosphite - α-aminophosphonates
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Representative
Procedure: Benzaldehyde (5 mmol), aniline (5 mmol) and triethyl
phosphite (5 mmol) were added successively and the mixture was stirred
for 15 min at r.t. After completion of the reaction (monitored by
TLC), the reaction mixture was adsorbed on silicagel and eluted
with petroleum ether-EtOAc (7:3) to give (phenyl-phenylamino-methyl)-phosphonic
acid diethylester. 1 H NMR (200 MHz, CDCl3 ): δ = 7.45
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H), 3.70-3.54 (m, 1 H), 1.26 (t, J = 7.4
Hz, 3 H), 1.08 (t, J = 6.7
Hz, 3 H). MS (FAB): m/z = 319 [M+ ],
210, 182, 119, 109, 91, 77, 55. FT-IR (KBr): 3310, 2924, 1452, 1239,
1029 cm-1 .
