Highly efficient O-silylation of alcohol with vinylsilane using a Rh(l)/HCl catalyst at room temperature

Organic Letters

Volumn 9, Issue 20, 2007, Pages 4073-4076

  Park, Jung Woo ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; HYDROCHLORIC ACID; RUTHENIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLSILANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE;

ALCOHOLS; CATALYSIS; HYDROCHLORIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RUTHENIUM; SILANES; TEMPERATURE; VINYL COMPOUNDS;

EID: 35048885491     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701909e     Document Type: Article

References (41)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1999; p 113.
2. (a) Morita, T.; Yoshida, S.; Okamoto, Y.; Sakurai, H. Synthesis 1979, 5, 379.
3. (b) Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549.
4. (a) Zhang, Z.-H.; Li, T.-S.; Yang, F.; Fu, C.-G. Synth. Commun. 1998, 28, 3105.
5. (b) Chrini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Synth. Commun. 1999, 29, 541.
6. (c) Karimi, B.; Golshani, B. J. Org. Chem. 2000, 65, 7228.
7. (d) Firouzabadi, H.; Iranpoor, N.; Amani, K.; Nowrouzi, F. J. Chem. Soc., Perkins Trans. 1 2002, 23, 2601.
8. (e) Firouzabadi, H.; Iranpoor, N.; Sobhani, S.; Ghassamipour, S.; Amoozgar, Z. Tetrahedron Lett. 2003, 44, 891.
9. (f) Azizi, N.; Saidi, M. R. Organometallics 2004, 23, 1457.
10. (g) Ghosh, A. K.; Bileer, G.; Schiltz, G. Synthesis 2001, 2203.
11. (h) List, B.; Castello, C. Synlett 2001, 1687.
12. (i) For an article of application to mesoporous silica surface, see: Zapilko, C.; Widenmeyer, M.; Nagl, I.; Estler, F.; Anwander, R.; Raudaschl-Sieber, G.; Groeger, O.; Engelhardt, G. J. Am. Chem. Soc. 2006, 128, 16266.
13. (a) Sinou, D.; Emziane, M. Synthesis 1986, 1045.
14. (b) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 6734.
15. Mai, K.; Patil, G. J. Org. Chem. 1986, 51, 3545.
16. (a) Morita, T.; Okamoto, Y.; Sakurai, H. Tetrahedron Lett. 1980, 21, 835.
17. (b) Olah, G. A.; Husain, A.; Gupta, B. G. B.; Salem, G. F.; Narang, S. C. J. Org. Chem. 1981, 46, 5212.
18. (c) Hosomi, A.; Sakurai, H. Chem. Lett. 1981, 1, 85.
19. (d) Olah, G. A.; Husain, A.; Singh, B. P. Synthesis 1983, 892.
20. (e) Suzuki, T.; Watahiki, T.; Oriyama, T. Tetrahedron Lett. 2000, 41, 8903.
21. (f) Shibata, T, Kanda, K, Ueno, Y.; Fujiwara, R. Bull. Chem. Soc. Jpn. 2006, 79, 1146.
22. Huang, X.; Craita, C.; Awad, L.; Vogel, P. Chem. Commun. 2005, 1297.
23. (a) For a review, see: Lukevics, E.; Dzintara, M. J. Organomet. Chem. 1985, 295, 265.
24. (b) Luo, X. L.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2527.
25. (c) Ito, H.; Watanabe, A.; Sawamura, M. Org. Lett. 2005, 7, 1869 and references cited therein.
26. (a) Tanabe, Y.; Okumura, H.; Maeda, A.; Murakami, M. Tetrahedron Lett. 1994, 35, 8413.
27. (b) Shirakawa, E.; Hironaka, K.; Otsuka, H.; Hayashi, T. Chem. Commun. 2006, 3927.
28. Park, J.-W.; Chang, H.-J.; Jun, C.-H. Synlett 2006, 5, 771.
29. Commercially available HCl dissolved in 1,4-dioxane was used without further purification.
30. van der Ent, A.; Onderdelinden, A. L. Inorg. Synth. 1973, 14, 92.
31. Complex 3c was prepared by olefin exchange reaction of chlorobis-(ethylene)rhodium(I) dimer (3b) with trimethylvinylsilane, and a crude identical spectra of 3c could be also obtained from 3a and 2a. BlażejewskaChadyniak, P.; Kubicki, M.; Maciejewski, H.; Marciniec, B. Inorg. Chim. Acta 2003, 350, 603-608.
32. For the related references of organometallic reactions incorporating an acid with transition-metal complexes, see: (a) Chung, M.-K.; Orlova, G.; Goddard, J. D.; Schlaf, M.; Harris, R.; Beveridge, T. J.; White, G.; Hallett, F. R. J. Am. Chem. Soc. 2002, 124, 10508.
33. (b) Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828. See also ref 9b.
34. For the related references of β-silyl elimination in silylative coupling of vinyl or aromatic compounds: (a) Kakiuchi, F.; Tanaka, Y.; Chatani, N.; Murai, S. J. Organomet. Chem. 1993, 456, 45-47.
35. (b) Marciniec, B.; Pietraszuk, C. Organometallics 1997, 16, 4320-4326.
36. (c) Marciniec, B.; Walczuk-Gusciora, E.; Blazejewska-Chadyniak, P. J. Mol. Catal. A: Chem. 2000, 160, 165-171.
37. (d) Marciniec, B.; Kujawa, M.; Pietraszuk, C. Organometallics 2000, 19, 1677-1681.
38. (e) Marciniec, B.; Walczuk-Gusciora, E.; Pietraszuk, C. Organometallics 2001, 20, 3423-3428.
39. (f) Marciniec, B.; Chadyniak, D.; Krompiec, S. Tetrahedron Lett. 2004, 45, 4065-4068.
40. (g) Kakiuchi, F.; Matsumoto, M.; Sonoda, M.; Fukuyama, T.; Chatani, N.; Murai, S. Chem. Lett. 2000, 7, 750-751.
41. For the recent review of silica-based organic-inorganic hybrid, see: Hoffmann, F.; Cornelius, M.; Morell, J.; Fröba, M.; Angew. Chem., Int. Ed. 2006, 45, 3216.