LiAlH4/silica chloride as a new chemoselective system for reduction of carbonyl compounds and phosphine oxides

Journal of the Iranian Chemical Society

Volumn 5, Issue 4, 2008, Pages 699-705

  Khalilzadeh, M A ^a   Hosseini, A ^a   Tajbakhsh, M ^a   Mohannazadeh, F ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b IRANIAN RESEARCH ORGANIZATION FOR SCIENCE AND TECHNOLOGY IROST   (Iran)

Author keywords

Carbonyl compounds; Lithium aluminium hydride; Phosphine oxides; Reduction; Silica chloride

Indexed keywords

EID: 57549095240     PISSN: 1735207X     EISSN: 17352428     Source Type: Journal    
DOI: 10.1007/BF03246152     Document Type: Article

References (33)

1. G.W. Kabalka, R.S. Verma, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, Pergamon, Vol. 8, Oxford, UK, 1991, p. 363.
2. nd ed., Wiley-VCH, New York, 1999, p. 823.
3. a) C.J. Fuller, E.L. Stangeland, T.C. Jackson, B. Singaram, Tetrahedron Lett. 40 (1994) 1515;
4. b) J.A. Dilts, E.C. Ashby, Inorg. Chem. 9 (1970) 855;
5. c) H.C. Brown, R.F. Mcfarlin, J. Am. Chem. Soc. 80 (1958) 5372;
6. d) H.C. Brown, C.J. Shoaf, J. Am. Chem. Soc. 86 (1964) 1079;
7. e) H.C. Brown, H.R. Deck, J. Am. Chem. Soc. 87 (1965) 562;
8. f) H.C. Brown, C.P. Garg, J. Am. Chem. Soc. 86 (1964) 1085;
9. g) H.C. Brown, A. Tsukamoto, J. Am. Chem. Soc. 86 (1964) 1089;
10. h) W. Parham, R. Soeder, R.M. Dodson, Chem. Commun. 84 (1962) 1756.
11. a) T. Imamoto, T. Takeyama, T. Kusumoto, Chem. Lett. (1985) 1491;
12. b) P.N. Kapoor, L.M. Venanzi, Helv. Chim. Acta 60 (1977) 2824;
13. c) V. Fehring, R. Kadyarov, M. Ludwig, J. Holz, K. Haage, R. Selke, J. Organomet. Chem. 1-2 (2001) 120;
14. d) P.W. Miller, M. Nieuwenhuyzen, X. Xu, S.L. James, Chem. Commun. 18 (2002) 2008;
15. e) M. Berthod, A. Favre-Reìguillon, J. Mohamad, G. Mignani, G. Docherty, M. Lemaire, Synlett 10 (2007) 1545;
16. f) A. Bootle-Wilbraham, S. Head, J. Longstaff, P. Wyatt, Tetrahedron Lett. 40 (1999) 5267;
17. g) S. Griffin, L. Heath, P. Wyatt, Tetrahedron Lett. 39 (1998) 4405.
18. T. Imamoto, S. Kikuchi, T. Miura, Y. Wada, Org. Lett. 3 (2001) 87.
19. C.A. Busacca, J.C. Lorenz, N. Grinberg, N. Haddad, M. Hrapchak, B. Latli, H. Lee, P. Sabila, A. Saha, M. Sarvestani, S. Shen, R. Varsolona, X. Wei, C.H. Senanayake, Org. Lett. 7 (2005) 4277.
20. D.B. Malpass, G.S. Yeargin, British Patent (1977) 1520237.
21. H. Mimoun, J. Org. Chem. 64 (1999) 2582.
22. B. Tamami, N.M. Goudarzian, J. Chem. Soc. Chem. Commun. (1994) 1079.
23. N.J. Lowrence, S.M. Bushell, Tetrahedron Lett. 41 (2000) 4570.
24. a) A.R. Gholap, N.S. Chakor, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Molecul. Cat. A: Chemical 245 (2006) 37;
25. b) F. Mohanazadeh, A.R. Momeni, Y. Ranjbar, Tetrahedron Lett. 35 (1994) 6127;
26. c) H. Firouzabadi, N. Iranpoor, B. Karimi, H. Hazarkhani, Synlett 2 (2000) 263;
27. d) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, B. Karimi, Synth. Commun. 33 (2003) 3671;
28. e) K.V.N.S Srinivas, I. Mahender, B. Das, Synthesis (2003) 2479;
29. e) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Phosphorus, Sulfur and Silicon 176 (2001) 165;
30. f) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, B. Karimi, J. Org. Chem. 67 (2002) 2572;
31. g) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Phosphorus, Sulfur and Silicon 177 (2002) 2847;
32. h) H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Tetrahedron Lett. 43 (2002) 7139;
33. i) H. Firouzabadi, H. Hazarkhani, H. Hassani, Phosphorus, Sulfur and Silicon 179 (2004) 403.