Browse > Article
http://dx.doi.org/10.5012/bkcs.2007.28.7.1167

Solvent-free Cyanosilylation of Carbonyl Compounds Catalyzed by NbCl5  

Georgea, Soney C. (Department of Chemistry, Inha University)
Kim, Sung-Soo (Department of Chemistry, Inha University)
Publication Information
Bulletin of the Korean Chemical Society / v.28, no.7, 2007 , pp. 1167-1170 More about this Journal
Abstract
A simple and convenient method for the addition of TMSCN to carbonyl compounds is described. NbCl5 is found to possess a strong Lewis acid property to transform carbonyl compounds smoothly to the corresponding cyanosilylether in high yields (up to 99 %) in solvent- free conditions.
Keywords
Cyanohydrins; Aldehydes; Ketones; Solvent-free; Nb$Cl_5$;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 6  (Related Records In Web of Science)
Times Cited By SCOPUS : 7
연도 인용수 순위
1 Vougioukas, A. E.; Kagan, H. B. Tetrahedron Lett. 1987, 28, 5513   DOI   ScienceOn
2 Kim, S. S.; Rajagopal, G.; George, S. C. Appl. Organomet. Chem. 2007, 21, 198   DOI   ScienceOn
3 Lidy, W.; Sundermeyer, W. Chem. Ber. 1973, 106, 587   DOI
4 Evans, D. A.; Truesdale, L. K. Tetrahedron Lett. 1973, 4929
5 Komatsu, N.; Uda, M.; Suzuki, H.; Takahashi, T.; Domae, T.; Wada, M. Tetrahedron Lett. 1997, 38, 7215   DOI   ScienceOn
6 Reetz, M. T.; Drewes, M. W.; Harms, K.; Reif, W. Tetrahedron Lett. 1988, 29, 3295   DOI   ScienceOn
7 Loh, T.-P.; Xu, K.-C.; Ho, D. S. C.; Sim, K.-Y. Synlett. 1998, 369
8 Kim, S. S.; Song, D. H. Eur. J. Org. Chem. 2005, 1777
9 Kim, S. S. Pure Appl. Chem. 2006, 78, 977   DOI   ScienceOn
10 Andrade, C. K. Z.; Azevedo, N. R. Tetrahedron Lett. 2001, 42, 6473   DOI   ScienceOn
11 Kim, S. S.; Rajagopal, G. Synthesis-stuttgart 2007, 2, 215
12 Kim, S. S.; Kwak, J. M.; Rajagopal, G. Bull. Korean Chem. Soc. 2006, 27, 1638   DOI   ScienceOn
13 Kim, S. S.; Rajagopal, G.; Song, D. H. J. Organomet. Chem. 2004, 689, 1734   DOI   ScienceOn
14 Kim, S. S.; Kim, D. W.; Rajagopal, G. Synthesis-Stuttgart 2004, 213
15 Kim, S. S.; Rajagopal, G.; Kim, D. W.; Song, D. H. Synth. Commun. 2004, 34, 2973   DOI   ScienceOn
16 Rajagopal, G.; Kim, S. S.; Kwak, J. M. Bull. Korean Chem. Soc. 2006, 27, 1907   DOI   ScienceOn
17 Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 8964   DOI   ScienceOn
18 Kim, S. S.; Kwak, J. M. Tetrahedron 2006, 62, 49   DOI   ScienceOn
19 Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Organic Lett. 2003, 5, 949   DOI   ScienceOn
20 Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384   DOI   ScienceOn
21 Harada, T.; Kanda, K. Organic lett. 2006, 8, 3817   DOI   ScienceOn
22 Cordoba, R.; Plumet, J. Tetrahedron Lett. 2003, 44, 6157   DOI   ScienceOn
23 Chen, F.-X.; Liu, X.; Qin, B.; Zhou, H.; Feng, X.; Zhang, G. Synthesis 2004, 14, 2266
24 Aspinall, H. C.; Bickley, J. F.; Greeves, N.; Kelly, R. V.; Smith, P. M. Organometallics 2005, 24, 3458   DOI   ScienceOn
25 Liu, Y.; Liu, X.; Xin, J.; Feng, X. Synlett 2006, 1085
26 Brunel, J. M.; Holmes, I. P. Angew. Chem. Int. Ed. 2004, 43, 2752   DOI   ScienceOn
27 Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412   DOI   ScienceOn
28 Gregory, R. J. H. Chem. Rev. 1999, 99, 3649   DOI   ScienceOn
29 Special symposium for the synthesis of nonracemic cyanohydrins, see: Tetrahedron 2004, 60, 10371   DOI   ScienceOn
30 Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491
31 Bandini, M.; Cozzi, P. G.; Garelli, A.; Melchiorre, P.; Umani- Ronchi, A. Eur. J. Org. Chem. 2002, 3243
32 Hatano, M.; Ikeno, T.; Miyamoto, T.; Ishihara, K. J. Am. Chem. Soc. 2005, 127, 10776   DOI   ScienceOn
33 Ortiz, A.; Quintero, L.; Hernandez, H.; Maldonado, S.; Mendoza, G.; Bernes, S. Tetrahedron Lett. 2003, 44, 1129   DOI   ScienceOn
34 Kabayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620   DOI   ScienceOn
35 Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371   DOI
36 Guo, Q.; Miyaji, T.; Hara, R.; Shen, B.; Takahashi, T. Tetrahedron 2002, 58, 7327   DOI   ScienceOn
37 Arai, S.; Sudo, Y.; Nishida, A. Synlett 2004, 6, 1104
38 Yadav, J. S.; Subba Reddy, B. V.; Eeshwaraiah, B.; Reddy, P. N. Tetrahedron 2005, 61, 875   DOI   ScienceOn
39 Yadav, J. S.; Narsaiah, A. V.; Subba Reddy, B. V.; Basak, A. K.; Nagaiah, K. J. Mol. Cat A: Chemi. 2005, 230, 107   DOI   ScienceOn
40 Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641   DOI   ScienceOn
41 Evans, D. A.; Truesdale, L. K.; Carroll, G. L. J. Chem. Soc. Chem. Commu. 1973, 55
42 Iwanami, K.; Aoyagi, M.; Oriyama, T. Tetrahedron Lett. 2005, 46, 7487   DOI   ScienceOn
43 Kurono, N.; Yamaguchi, M.; Suzuki, K.; Ohkuma, T. J. Org. Chem. 2005, 70, 6530   DOI   ScienceOn
44 Howarth, J.; Gillespie, K. Tetrahedron Lett. 1996, 37, 6011   DOI   ScienceOn
45 Kim, S. S.; Lee, S. H. Synth. Commun. 2005, 35, 751   DOI   ScienceOn
46 Kim, S. S.; Lee, S. H.; Kwak, J. M. Tetrahedron: Asymmetry 2006, 17, 1165   DOI   ScienceOn
47 Andrade, C. K. Z.; Oliveira, G. R. Tetrahedron Lett. 2002, 43, 1935   DOI   ScienceOn
48 Liu, X.; Qin, B.; Zhou, X.; He, B.; Feng, X. J. Am. Chem. Soc. 2005, 127, 12224   DOI   ScienceOn