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Acknowledgments
Pohl, M. M.; Radnik, J.; Hubner, S.; Jahnisch, K.; Bruckner, A.; Beller, M. J. Am.
Chem. Soc. 2009, 131, 1775; (e) Aliaga, M. J.; Ramon, D. J.; Yus, M. Org. Biomol.
Chem. 2010, 8, 43; (f) Shylesh, S.; Schunemann, V.; Thiel, W. R. Angew. Chem.,
Int. Ed. 2010, 49, 3428; (g) Schätz, A.; Reiser, O.; Stark, W. J. Chem. Eur. J. 2010,
16, 8950.
A.V.G. and G.G.K.S.N.K. thank CSIR, New Delhi for the award of
fellowships. The authors also thank Dr. J. S. Yadav, Director, IICT
for his kind encouragement and support.
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12. General procedure: Nano-Fe3O4 (0.05 mmol) was added to
a mixture of
carbonyl compound (1 mmol), amine (1 mmol) and diethyl phosphite
(1.2 mmol). The resulting mixture was heated at 50 °C in an orbital shaker
incubator for the appropriate reaction time (Table 1). After completion of the
reaction, as indicated by TLC, the reaction mixture was diluted with ethyl
acetate and the nanoparticles were separated with an external magnet and
then washed twice with ethyl acetate. The combined organic layers were
concentrated in vacuo and the resulting residue was purified by silica gel
column chromatography (70:30, hexane/ethyl acetate) to afford the pure
a-
amino phosphonate. The products thus obtained were characterized by IR,
NMR, and mass spectroscopy. The spectral data were found to be consistent
with authentic samples.7,8
Spectral data for unknown product: Compound 3p: Diethyl phenyl(3,4,5-
trimethoxyphenylamino)methylphosphonate: Solid, mp 121–123 °C. IR (KBr):
8. (a) Mitragotri, S. D.; Pore, D. M.; Desai, U. V.; Wadgaonkar, P. P. Catal. Commun.
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Baghbanian, S. M.; Khaksar, S. Tetrahedron Lett. 2008, 49, 6501; (c) Ambica, K.
S.; Taneja, S. C.; Hundal, M. S.; Kapoor, K. K. Tetrahedron Lett. 2008, 49, 2208; (d)
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Am. Chem. Soc. 2009, 131, 8262; (b) Shiju, N. R.; Guliants, V. V. Appl. Catal. A Gen.
2009, 356, 1; (c) Rosario-Amorin, D.; Wang, X.; Gaboyard, M.; Clerac, R.; Nlate,
m
3309, 2928, 2850, 1720, 1605, 1508, 1454, 1414, 1237, 1127, 1022, 968, 782,
701 cmÀ1 1H NMR (300 MHz, CDCl3): d 7.46–7.38 (m, 2H), 7.34–7.22 (m, 3H),
.
5.76 (s, 2H), 4.85–4.73 (br s, 1H), 4.63 (d, 1H, J = 23.9 Hz), 4.18–4.05 (m, 2H),
3.93–3.81 (m, 1H), 3.68 (s, 6H), 3.65 (s, 3H), 3.68–3.54 (m, 1H), 1.32 (t, 3H,
J = 6.9 Hz), 1.10 (t, 3H, J = 6.9 Hz). 13C NMR (75 MHz, CDCl3): d 153.6, 142.8,
135.9, 128.6, 127.9, 127.7, 127.6, 91.4, 63.2, 60.9, 57.5, 55.6, 16.4. LC–MS: m/z
(%): (M++H) 410. HRMS calcd for C20H29NO6P: 410.1732, found: 410.1736.