Micellar solution of sodium dodecyl sulfate (SDS) catalyzes Kabacknik-Fields reaction in aqueous media

Synthesis

Volumn , Issue 11, 2009, Pages 1909-1915

  Sobhani, Sara ^a   Vafaee, Asieh ^a  

^a UNIVERSITY OF BIRJAND   (Iran)

Author keywords

aminophosphonates; Aldehydes; Amines; Aqueous media; Micelles; Sodium dodecyl sulfate

Indexed keywords

AMINOPHOSPHONATES; AQUEOUS MEDIA; HIGH-YIELDING PROCEDURES; INTERMEDIATE FORMATION; MICELLAR SOLUTION; ONE-POT SYNTHESIS; SODIUM DODECYL SULFATE; THREE COMPONENT REACTIONS;

ALDEHYDES; AMINATION; AMINES; DIFFUSERS (OPTICAL); MICELLES; SODIUM;

SODIUM SULFATE;

ALDEHYDE; AMINE; DIETHYL ALPHA AMINOPHOSPHONATE DERIVATIVE; DIETHYLPHOSPHITE; DODECYL SULFATE SODIUM; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; KABACKNIK FIELDS REACTION; MICELLE; ONE POT SYNTHESIS; REACTION ANALYSIS;

EID: 67650082401     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216789     Document Type: Article

References (52)

1. (a) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley and Sons: New York, 1997.
2. (b) Organic Reactions in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
3. Anastas, P.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.
4. (a) Rideout, D. C.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816.
5. (b) Breslow, R. Acc. Chem. Res. 1991, 24, 159.
6. (c) Engberts, J. B. F. N.; Blandamer, M. Chem. Commun. 2001, 1701.
7. (a) Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systems; Academic Press: London, 1975.
8. (b) Mixed Surfactant Systems; Holland, P. M.; Rubingh, D. N., Eds.; American Chemical Society: Washington DC, 1992.
9. (c) Structure and Reactivity in Aqueous Solution; Cramer, C. J.; Truhlar, D. G., Eds.; American Chemical Society: Washington DC, 1994.
10. (d) Surfactant-Enhanced Subsurface Remediation; Sabatini, D. A.; Knox, R. C.; Harwell, J. H., Eds.; American Chemical Society: Washington DC, 1994.
11. (e) Manabe, K.; Sun, X. M.; Kobayashi, S. S. J. Am. Chem. Soc. 2001, 123, 10101.
12. (a) Stein, T. M.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 3943.
13. (b) Myers, D. Surfactant Science and Technology; Wiley-VCH: Weinheim, 1992.
14. (c) Fendler, J. H. Membrane Mimetic Chemistry; Wiley: New York, 1982.
15. Tascioglu, S. Tetrahedron 1996, 52, 11113; and references therein.
16. (a) Berezin, I. V.; Martinek, K.; Yatsimirski, A. K. Russ. Chem. Rev. 1973, 42, 787.
17. (b) Menger, F. M.; Rhee, J. U.; Rhee, H. K. J. Org. Chem. 1975, 40, 3803.
18. (c) Larpent, C.; Bernard, E.; Menn, F. B.; Patin, H. J. Mol. Catal. A: Chem. 1997, 116, 277.
19. (d) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem. Int. Ed. 1998, 37, 2581.
20. (e) Grassert, I.; Schmidt, U.; Ziegler, S.; Fischer, C.; Oehme, G. Tetrahedron: Asymmetry 1998, 9, 4193.
21. (f) Selke, R.; Holz, J.; Riepe, A.; Borner, A. Chem. Eur. J. 1998, 4, 769.
22. (g) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593.
23. (h) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381.
24. (i) Goedheijt, M. S.; Hanson, B. E.; Reek, J. N. H.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2000, 122, 1650.
25. (a) Iranpoor, N.; Firouzabadi, H.; Shekarrize, M. Org. Biomol. Chem. 2003, 1, 724.
26. (b) Firouzabadi, H.; Iranpoor, N.; Amani, K. Green Chem. 2001, 3, 131.
27. (c) Firouzabadi, H.; Iranpoor, N.; Garzan, A. Adv. Synth. Catal. 2005, 347, 1925.
28. (d) Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. Adv. Synth. Catal. 2005, 347, 655.
29. Kafarski, P.; Lejezak, B. Phosphorus Sulfur Silicon Relat. Elem. 1991, 63, 193.
30. (a) Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. J. Med. Chem. 1989, 32, 1652.
31. (b) Giannousis, P. P.; Bartlett, P. A. J. Med. Chem. 1987, 30, 1603.
32. Hirschmann, R.; Smith, A. B. III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengler, P. A.; Venkovic, S. J. Science 1994, 265, 234.
33. (a) Baylis, E. K.; Campell, C. D.; Dingwall, J. G. J. Chem. Soc., Perkin Trans. 1 1984, 1, 2845.
34. (b) Atheron, F. R.; Hassal, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29.
35. (a) Laschat, S.; Kunz, H. Synthesis 1992, 90.
36. (b) Genet, J. P.; Yziel, J.; Port, M.; Touzin, A. M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett. 1992, 33, 77.
37. Qian, C.; Huang, T. J. Org. Chem. 1998, 63, 4125.
38. (a) Mu, X. J.; Lei, M. Y.; Zou, J. P.; Zhang, W. Tetrahedron Lett. 2006, 47, 1125.
39. (b) Xia, M.; Lu, Y. D. Ultrason. Sonochem. 2006, 235.
40. (c) Zahouily, M.; Elmakssoudi, A.; Mezdar, A.; Rayadh, A.; Sebti, S. Catal. Commun. 2007, 8, 225.
41. (d) Mitragotri, S. D.; Pore, D. M.; Desai, U. V.; Wadgaonkar, P. P. Catal. Commun. 2008, 9, 1822.
42. (e) Wu, J.; Sun, W.; Sun, X.; Xia, H. G. Green Chem. 2006, 8, 365.
43. (f) Akiyama, T.; Sanada, M.; Fuchibe, K. Synlett 2003, 1463.
44. (g) Kaboudin, B.; Sorbiun, M. Tetrahedron Lett. 2007, 48, 9015.
45. (h) Kaboudin, B. Chem. Lett. 2001, 880.
46. (i) Kaboudin, B.; Saadati, F. Synthesis 2004, 1249.
47. (a) Sobhani, S.; Tashrifi, Z. Synth. Commun. 2009, 39, 120.
48. (b) Sobhani, S.; Safaei, E.; Asadi, M.; Jalili, F. J. Organomet. Chem. 2008, 693, 3313.
49. (c) Sobhani, S.; Safaei, E.; Asadi, M.; Jalili, F.; Tashrifi, Z. J. Porphyrins Phthalocyanines 2008, 12, 849.
50. (d) Sobhani, S.; Tashrifi, Z. Heteroat. Chem. 2009, 20, 109.
51. (a) Jönsson, B.; Lindman, B.; Holmberg, K.; Kronberg, B. Surfactants and Polymers in Aqueous Solution; Wiley: Chichester, 1998, 37 and 45.
52. (b) Rosen, M. J. Surfactants and Interfacial Phenomena; Wiley: New York, 1989, 122-132.