Iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily available, non-hygroscopic, non-corrosive, highly stable and a reusable Lewis Acid catalyst: Efficient O-silylation of α-hydroxyphosphonates, alcohols and phenols by hexamethyldisilazane (HMDS) under solvent-free conditions

Journal of Organometallic Chemistry

Volumn 693, Issue 16, 2008, Pages 2711-2714

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Jafari, Abbas Ali ^b   Jafari, Mohammad Reza ^c  

^a SHIRAZ UNIVERSITY   (Iran)

^b YAZD UNIVERSITY   (Iran)

^c SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Hydroxyphosphonate; Hexamethyldisilazane; Hydroxy compounds; Iron(III) trifluoroacetate; Trimethylsilyl ether

Indexed keywords

IRON COMPOUNDS; PHENOLS;

EXCELLENT YIELDS; HYDROXYL GROUPS; IRON (III); SILYLATION; TRIFLUOROACETATE (TFA);

IRON;

EID: 47049127383     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.05.018     Document Type: Article

References (44)

1. Wuts P.G.M., and Greene T.W. Green's Protective Groups in Organic Synthesis. 4th ed. (2007), John Wiley & Sons, Hoboken, NJ
2. Lalonde M., and Chan T.H. Synthesis (1985) 817
3. Brook M.A. Silicon in Organic, Organometallic, and Polymer Chemistry (2000), Wiley, New York
4. Morita T., Okamoto Y., and Sakurai H. Tetrahedron Lett. 21 (1980) 835
5. Vesoglu T., and Mitscher L.A. Tetrahedron Lett. 22 (1981) 1299
6. Bifiss A., Castello E., Zecca M., and Basato M. Tetrahedron 57 (2001) 10391
7. Hayashi M., Matsuura Y., and Watanabe Y. Tetrahedron Lett. 45 (2004) 1409
8. Hosomi A., and Sakurai H. Chem. Lett. 85 (1981) 880
9. Veysoglu T., and Mitscher L.A. Tetrahedron Lett. 22 (1981) 1299
10. Hosomi A., and Sakurai H. Chem. Lett. (1981) 85
11. Olah G.A., Husain A., Gupta B.G.B., Salem G.F., and Narang S.C. J. Org. Chem. 46 (1981) 5212
12. Suzuki T., Watahiki T., and Oriyama T. Tetrahedron Lett. 41 (2000) 8903
13. Shirakawa E., Hironaka K., Otsuka H., and Hayashi T. Chem. Commun. (2006) 3927
14. Karimi B., and Golshani B. J. Org. Chem. 65 (2000) 7228
15. Langer S.H., Connell S., and Wender J. J. Org. Chem. 23 (1958) 50
16. Gauuret P., El-Ghamarli S., Legrand A., Couirier D., and Rigo B. Synth. Commun. 26 (1996) 707
17. Zhang Z.H., Li T.S., Yang F., and Fu C.G. Synth. Commun. 28 (1998) 3105
18. Mojtahedi M.M., Saidi M.R., Bolourtchian M., and Heravi M. Phosphorus, Sulfur Silicon Relat. Elem 177 (2002) 289
19. Tillu V.H., Jadhav V.H., Borate H.B., and Wakharkar R.D. Arkivok (2004) 83
20. Azizi N., and Saidi M.R. Organometallics 23 (2004) 1457
21. Azizi N., Yousefi R., and Saidi M.R. J. Organomet. Chem. 691 (2006) 817
22. Khazaei A., Zolfigol M.A., Tanbakouchian Z., Shiri M., Niknam K., and Saien J. Catal. Commun. 8 (2007) 917
23. Ghorbani-Vaghei R., Zolfigol M.A., Chegeny M., and Veisi H. Tetrahedron Lett. 47 (2006) 4505
24. Narsaiah A.V. J. Organomet. Chem. 692 (2007) 3614
25. Zareyeea D., and Karimi B. Tetrahedron Lett. 48 (2007) 1277
26. Firouzabadi H., and Karimi B. Synth. Commun. 23 (1993) 1633
27. Firouzabadi H., Sardarian A.R., Khayat Z., Karimi B., and Tangestaninezhad S. Synth. Commun. 27 (1997) 2709
28. Firouzabadi H., Iranpoor N., and Sobhani S. Tetrahedron Lett. 43 (2002) 3653
29. Firouzabadi H., Sardarian A.R., and Khayat Z. Iran. J. Chem. Chem. Eng. 15 (1996) 91
30. Firouzabadi H., Iranpoor N., Amani K., and Nowrouzi F. J. Chem. Soc., Perkin Trans. 1 (2002) 2601
31. Firouzabadi H., Iranpoor N., Sobhani S., and Ghassamipour S. Synthesis (2005) 595 and the references cited therein
32. Firouzabadi H., Iranpoor N., Sobhani S., Ghassamipour S., and Amoozgar Z. Tetrahedron Lett. 44 (2003) 891 and the references cited therein
33. Firouzabadi H., Iranpoor N., Sobhani S., and Ghassamipour S. J. Organomet. Chem. 689 (2004) 3197 and the references cited therein
34. Iranpoor N., and Adibi H. Bull. Chem. Soc. Jpn. 73 (2000) 675
35. Tanaka K., and Toda F. Chem. Rev. 100 (2000) 1025
36. Varma R.S. Green Chem. (1999) 43
37. Kabachnik M.M., Synatkova E.V., Novikova Z.S., Abramova G.L., Rozhkova N.G., and Andreeva E.I. Vesthn. Mosk. Univ. Ser. 2: Khim. 31 (1990) 384
38. G.H. Birum, G.A. Richardson, US Patent, 3,113,139 (to Monsanto Chem. Co), December, 3 (1963); Chem. Abstr. 60 (1964) 5551d.
39. Koenigkramer R.E., and Zimmer H. Tetrahedron Lett. 21 (1980) 1017
40. Olah G.A., and Wu A. J. Org. Chem. 56 (1991) 902
41. Sekine M., Nakajima M., and Hata T. Bull. Chem. Soc. Jpn. 54 (1982) 218
42. Hata T., Hashizume A., Nakajima M., and Sekine M. Tetrahedron Lett. 19 (1978) 63
43. Sekine M., Nakajima M., Kume A., and Hashizume A. Bull. Chem. Soc. Jpn. 55 (1982) 224
44. Trusedale K., and Takacs J.M. Tetrahedron Lett. 29 (1978) 2495