Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispread in silica gel under neutral condition

Journal of Organometallic Chemistry

Volumn 691, Issue 5, 2006, Pages 817-820

  Azizi, Najmedin ^a   Yousefi, Rozbeh ^a   Saidi, Mohammad R ^a  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Alcohol; Hexamethyldisilazane; Hydroxyl group; Lithium perchlorate; LP SiO2; Phenol; Recycling; Regioselective; Silica gel; Silylation

Indexed keywords

ALCOHOLS; GELS; LITHIUM COMPOUNDS; ORGANOMETALLICS; PHENOLS; SILICA;

HEXAMETHYLDISILAZANE; HYDROXYL GROUPS; LITHIUM PERCHLORATE; LP-SIO2; REGIOSELECTIVE; SILICA GELS; SILYLATION;

ORGANIC CHEMICALS;

EID: 31644440633     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.11.005     Document Type: Article

References (27)

1. G. Van Look, G. Simchen, and J. Heberle Silylation Agents 1995 Fluka Buchs, Switzerland
2. M.A. Brook Silicon in Organic, Organometallic, and Polymer Chemistry 2000 Wiley New York
3. T. Morita, Y. Okamoto, and H. Sakurai Tetrahedron Lett. 21 1980 835
4. T. Vesoglu, and L.A. Mitscher Tetrahedron Lett. 22 1981 1299
5. X. Huang, C. Craita, L. Awad, and P. Vogel Chem. Commun. 2005 1297
6. A. Hosomi, and H. Sakurai Chem. Lett. 85 1981 880
7. G.A. Olah, A. Husain, B.G.B. Gupta, G.F. Salem, and S.C. Narang J. Org. Chem. 46 1981 5212
8. T. Suzuki, T. Watahiki, and T. Oriyama Tetrahedron Lett. 41 2000 8903
9. T. Watahiki, M. Masaya, and T. Oriyama Green Chem. 5 2003 82
10. H. Firouzabadi, and B. Karimi Synth. Commun. 23 1993 1633
11. H. Firouzabadi, A.R. Sardarian, Z. Hayat, B. Karimi, and S. Tangestaninejad Synth. Commun. 27 1997 2709
12. H. Firouzabadi, N. Iranpoor, K. Amani, and F. Nowrouzi J. Chem. Soc., Perkin Trans. 1 2002 2601
13. B. Karimi, and B. Golshani J. Org. Chem. 65 2000 7228
14. S.H. Langer, S. Connell, and J. Wender J. Org. Chem. 23 1958 50
15. P. Gauuret, S. El-Ghamarli, A. Legrand, D. Couirier, and B. Rigo Synth. Commun. 26 1996 707
16. Z.H. Zhang, T.S. Li, F. Yang, and C.G. Fu Synth. Commun. 28 1998 3105
17. D. Amantini, F. Fringuelli, F. Pizzo, and L. Vaccaro J. Org. Chem. 66 2001 6734
18. V.H. Tillu, V.H. Jadhav, H.B. Borate, and R.D. Wakharkar Arkivoc XIV 2004 83
19. M.M. Mojtahedi, M.R. Saidi, M. Bolourtchian, and M.M. Heravi Phosphorus Sulfur Silicon Relat. Elem. 177 2002 289
20. F. Shirini, M.A. Zolfigol, and K. Mohammadi Phosphorus Sulfur Silicon Relat. Elem. 178 2003 1567
21. M.R. Saidi, and N. Azzizi Synlett 2002 347
22. S. Sankararaman, and J.E. Nesakumar Eur. J. Org. Chem. 2000 2003
23. N. Azizi, and M.R. Saidi Tetrahedron 60 2004 383
24. N. Azizi, and M.R. Saidi Eur. J. Org. Chem. 2003 4630
25. N. Azizi, and M.R. Saidi J. Organomet. Chem. 688 2003 283
26. N. Azizi, and M.R. Saidi Organometallics 23 2004 1457
27. Lithium perchlorate dispersed on silica gel has been prepared by simple mixing of both reagent in acetonitriles or diethyl ether and removing of the solvent and drying in vacuum.