Sulfated zirconia: An efficient catalyst for solvent-free synthesis of silyl ethers under mild conditions

Synthetic Communications

Volumn 41, Issue 14, 2011, Pages 2064-2072

  Thirupathi, Boningari ^a   Prasad, Avvari N ^a   Srinivas, Rapelli ^a   Reddy, Benjaram M ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Heterogeneous catalyst; Silylation of alcohols; Solid acid; Solvent free; Sulfated zirconia

Indexed keywords

(3,7 DIMETHYLOCTA 2,6 DIENYLOXY)TRIMETHYLSILANE; 1,2 DIPHENYL 2 (TRIMETHYLSILYLOXY)ETHANAMINE; 2,2,8,8 TETRAMETHYL 3,7 DIOXA 2,8 DISILANONANE; 2,2,8,8 TETRAMETHYL 5 (TRIMETHYLSILYLOXY) 3,7 DIOXA 2,8 DISILANONANE; ACETONITRILE; BENZENE; CYCLOHEXANONE O TRIMETHYLSILYL OXIME; CYCLOHEXYLOXYTRIMETHYLSILANE; ENZHYDRYLOXYTRIMETHYLSILANE; METHANOL; SOLVENT; TOLUENE; TRIMETHYL(1 PHENYLETHOXY)SILANE; TRIMETHYL(3 PHENYLPROPOXY)SILANE; TRIMETHYL(NAPHTHALEN 2 YLOXY)SILANE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CATALYST; CHEMICAL STRUCTURE; ENVIRONMENTAL TEMPERATURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SILYLATION;

EID: 79957656139     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.497591     Document Type: Article

References (41)

1. Kocienski, P. J. Protecting Groups, 3rd ed.; Georg Thieme: Stuttgart, 2005.
2. Mei Xiao, H. Y.; Suzane, M. K.; Christian, M. M.; William, L. S.; Yu, L. J. Facile synthesis of anticancer drug NCX 4040 in mild conditions. Lett. Org. Chem. 2008, 5, 510-513;
3. Sartori, G.; Ballani, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Protection (and deprotection) of functional groups in organic synthesis by heterogeneous catalysis. Chem. Rev. 2004, 104, 199-250.
4. Davies, J. S.; Higginbotham, C. L.; Tremeer, E. J.; Brown, C.; Treadgold, R. C. Protection of hydroxy groups by silylation: Use in peptide synthesis and as lipophilicity modifiers for peptides. J. Chem. Soc., Perkin Trans. 1 1992, 3043-3048.
5. Morita, T.; Yoshida, S.; Okamoto, Y.; Sakurai, H. Chlorotrimethylsilane/ sodium iodide: A new reagent for conversion of alcohols into iodides. Synthesis 1979, 5, 379-380;
6. Corey, E. J.; Snider, B. B. A Total synthesis of (±)-fumagillin. J. Am. Chem. Soc. 1972, 94, 2549-2550.
7. Langer, S. H.; Connell, S.; Wender, I. Preparation and properties of trimethylsilyl ethers and related compounds. J. Org. Chem. 1958, 23, 50-58.
8. Sinou, D.; Emziane, M. Trimethylsilylazide: A highly reactive silylating agent for primary and secondary alcohols. Synthesis 1986, 1045-1046;
9. Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Efficient O-trimethylsilylation of alcohols and phenols with trimethylsilyl azide catalyzed by tetrabutylammonium bromide under neat conditions. J. Org. Chem. 2001, 66, 6734-6737. (Pubitemid 32946593)
10. Jacqueline, D. H.; Chan, W. H.; Ashley, D. L.; William, R. R. Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers. Org. Lett. 2007, 9, 5621-5624.
11. Morita, T.; Okamoto, Y.; Sakurai, H. Use of allysilanes as a new type of silylating agent for alcohols and carboxylic acids. Tetrahedron Lett. 1980, 21, 835-838;
12. Olah, G. A.; Husain, A.; Gupta, B. G. B.; Salem, G. F.; Narang, S. C. Synthetic methods and reactions, 104: Silylations with in situ generated trimethylsilyl triflate reagent systems. J. Org. Chem. 1981, 46, 5212-5214;
13. Hosomi, A.; Sakurai, H. Protection of alcohols and acids with allylsilanes catalyzed by iodine or iodotrimethylsilane in chlorinated hydrocarbon. Chem. Lett. 1981, 10, 85-88;
14. Olah, G. A.; Husain, A.; Singh, B. P. Catalysis by solid superacids, 19: Simplified and improved polymeric perfluorinated resin sulfonic acid (Nafion-H) catalyzed protection-deprotection reactions. Synthesis 1983, 892-896;
15. Suzuki, T.; Watahiki, T.; Oriyama, T. A novel and efficient method for the silylation of alcohols with methallylsilanes catalyzed by Sc(OTf)3. Tetrahedron Lett. 2000, 41, 8903- 8906;
16. Shibata, T.; Kanda, K.; Ueno, Y.; Fujiwara, R. Cationic Au(I)- and Pt(II)-catalyzed silylation of alcohols using allylsilanes. Bull. Chem. Soc. Jpn. 2006, 79, 1146-1147. (Pubitemid 44681204)
17. Hajime, I.; Katsuhiro, T.; Takahiro, M.; Masaya, S. Gold(I)-phosphine catalyst for the highly chemoselective dehydrogenative silylation of alcohols. Org. Lett. 2005, 7, 3001-3004.
18. Zhang, Z.-H.; Li, T.-S.; Yang, F.; Fu, C.-G. Montmorillonite clay catalysis XI: Protection and deprotection of hydroxyl group by formation and cleavage of trimethylsilyl ethers catalysed by montmorillonite K-10. Synth. Commun. 1998, 28, 3105-3114; (Pubitemid 28384432)
19. Chrini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Heterogeneous catalysis in trimethylsilylation of alcohols and phenols by zirconium sulfophenyl phosphonate. Synth. Commun. 1999, 29, 541-546; (Pubitemid 29088744)
20. 40) as a heterogeneous inorganic catalyst: Activation of hexamethyldisilazane (HMDS) by tungstophosphoric acid for efficient and selective solvent-free O-silylation reactions. J. Chem. Soc., Perkins Trans. 1 2002, 23, 2601-2604;
21. 2] is an efficient and mild catalyst for the silylation of α-hydroxyphosphonates to a-trimethylsilyloxyphosphonates with HMDS at room temperature. Tetrahedron Lett. 2003, 44, 891-893. (Pubitemid 36183197)
22. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999.
23. Firouzabadi, H.; Karimi, B. Zinc chloride-catalyzed silylation of alcohols and phenols by hexamethyldisilazane: A highly chemoselective reaction. Synth. Commun. 1993, 23, 1633-1641. (Pubitemid 23188570)
24. Firouzabadi, H.; Sardarian, A. R.; Khayat, Z.; Karimi, B.; Tangestaninejad, S. Nitrogen ligand complexes of metal chlorides as effective catalysts for the highly regio- and chemoselective silylation of hydroxyl groups with hexamethyldisilazane (HMDS) at room temperature. Synth. Commun. 1997, 27, 2709-2719. (Pubitemid 27297721)
25. Karimi, B.; Golshani, B. Mild and highly efficient method for the silylation of alcohols using hexamethyldisilazane catalyzed by iodine under nearly neutral reaction conditions. J. Org. Chem. 2000, 65, 7228-7230.
26. Azizi, N.; Saidi, M. R. Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions. Organometallics 2004, 23, 1457-1458.
27. Akhlaghinia, B.; Tavakoli, S. An efficient method for the protection of alcohols and phenols by using hexamethyldisilazane in the presence of cupric sulfate pentahydrate under neutral reaction conditions. Synthesis 2005, 1775-1778. (Pubitemid 41058559)
28. Bruynes, A. C.; Jurriens, T. K. S. Catalysts for silylations with 1,1,1,3,3,3-hexamethyldisilazane. J. Org. Chem. 1982, 47, 3966-3969.
29. Uppadhya, T. T.; Daniel, T.; Sudalai, A.; Ravindranathan, T.; Sabu, K. R. Natural kaolinitic clay: A mild and efficient catalyst for the tetrahydropyranylation and trimethylsilylation of alcohols. Synth. Commun. 1996, 26, 4539-4544.
30. Riemer, T.; Spielbauer, D.; Hunger, M.; Mekhemer, G. A.; Knozinger, H. Superacid properties of sulfated zirconia as measured by Raman and 1H MAS NMR spectroscopy. J. Chem. Soc., Chem. Commun. 1994, 1181-1182.
31. Sarkar, A.; Yemul, O. S.; Bandgar, B. P.; Gaikwad, N. B.; Wadgaonkar, P. P. Sulfated zirconia as an efficient catalyst for tetrahydropyranylation and acetalization. Org. Prep. Proced. Int. 1996, 28, 613-618.
32. Reddy, B. M.; Sreekanth, P. M. An efficient zirconia catalyst for solvent-free tetrahydropyranylation of alcohols and phenols. Synth. Commun. 2002, 32, 3561-3564. (Pubitemid 35278844)
33. Reddy, B. M.; Thirupathi, B.; Patil, M. K. Highly efficient promoted zirconia solid acid catalysts for synthesis of α-aminonitriles using trimethylsilyl cyanide. J. Mol. Catal. A: Chem. 2009, 307, 154-159.
34. Reddy, B. M.; Thirupathi, B.; Patil, M. K. Activation of trimethylsilyl cyanide and mechanistic investigation for facile cyanosilylation by solid acid catalysts under mild and solvent-free conditions. Appl. Catal. A: General 2010, 384, 147-153.
35. Reddy, B. M.; Patil, M. K. Organic syntheses and transformations catalyzed by sulfated zirconia. Chem. Rev. 2009, 109, 2185-2208;
36. Reddy, B. M.; Patil, M. K.; Reddy, B. T.; Park, S.-E. Efficient synthesis of β-amino alcohols by regioselective ring opening of epoxides with anilines catalyzed by sulfated zirconia under solvent-free conditions. Catal. Commun. 2008, 9, 950-954; (Pubitemid 351191886)
37. Reddy, B. M.; Patil, M. K. Promoted zirconia solid acid catalysts for organic synthesis. Curr. Org. Chem. 2008, 12, 118-140;
38. 2 solid acid catalyst for classical Mannich reaction. Catal. Lett. 2008, 125, 97-103;
39. Reddy, B. M.; Patil, M. K.; Reddy, B. T. An efficient protocol for aza-Michael reactions under solvent-free condition employing sulfated zirconia catalyst. Catal. Lett. 2008, 126, 413-418.
40. Reddy, B. M.; Sreekanth, P. M.; Reddy, V. R. Modified zirconia solid acid catalysts for organic synthesis and transformations. J. Mol. Catal. A: Chem. 2005, 225, 71-78.
41. Reddy, B. M.; Patil, M. K.; Reddy, G. K.; Reddy, B. T.; Rao, K. N. Selective tert-butylation of phenol over molybdate- and tungstate-promoted zirconia catalysts. Appl. Catal. A: Gen. 2007, 332, 183-191. (Pubitemid 47562731)