Cyanosilylation of carbonyl compounds with trimethylsilyl cyanide catalyzed by an yttrium-pillared silicotungstate dimer

Angewandte Chemie - International Edition

Volumn 51, Issue 15, 2012, Pages 3686-3690

  Kikukawa, Yuji ^a   Suzuki, Kosuke ^a   Sugawa, Midori ^a   Hirano, Tomohisa ^a   Kamata, Keigo ^a   Yamaguchi, Kazuya ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

carbonyl compounds; cyanosilylation; polyoxometalate; trimethylsilyl cyanide; yttrium

Indexed keywords

CATALYTIC PERFORMANCE; CYANOSILYLATION; POLYOXOMETALATES; TRIMETHYLSILYL CYANIDE; TRIMETHYLSILYL ETHERS; TURNOVER FREQUENCY; TURNOVER NUMBER;

ALDEHYDES; CARBONYL COMPOUNDS; CATALYSIS; ETHERS; KETONES; ORGANIC COMPOUNDS; YTTRIUM; YTTRIUM ALLOYS;

CYANIDES;

CYANIDE; HYDROCARBON; KETONE; SILICON; TRIMETHYLSILYL CYANIDE; TRIMETHYLSILYL DERIVATIVE; TUNGSTEN; TUNGSTEN DERIVATIVE; YTTRIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; CYANIDES; HYDROCARBONS; KETONES; MODELS, MOLECULAR; SILICON; TRIMETHYLSILYL COMPOUNDS; TUNGSTEN; TUNGSTEN COMPOUNDS; YTTRIUM;

EID: 84859530380     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201200486     Document Type: Article

References (57)

1. R. J. H. Gregory, Chem. Rev. 1999, 99, 3649
2. J.-M. Brunel, I. P. Holmes, Angew. Chem. 2004, 116, 2810
3. Angew. Chem. Int. Ed. 2004, 43, 2752, and references therein.
4. B. Y. Park, K. Y. Ryu, J. H. Park, S.-g. Lee, Green Chem. 2009, 11, 946
5. N. Kurono, M. Yamaguchi, K. Suzuki, T. Ohkuma, J. Org. Chem. 2005, 70, 6530
6. M. Bandini, P. G. Cozzi, A. Garelli, P. Melchiorre, A. Umani-Ronchi, Eur. J. Org. Chem. 2002, 3243
7. P. Saravanan, R. V. Anand, V. K. Singh, Tetrahedron Lett. 1998, 39, 3823
8. Y. Yang, D. Wang, Synlett 1997, 1379
9. J. K. Whitesell, R. Apodaca, Tetrahedron Lett. 1996, 37, 2525
10. S. Matsubara, T. Takai, K. Utimoto, Chem. Lett. 1991, 1447
11. S. Kobayasi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 537
12. R. Noyori, S. Murata, M. Suzuki, Tetrahedron 1981, 37, 3899.
13. Y. Ogasawara, S. Uchida, K. Yamaguchi, N. Mizuno, Chem. Eur. J. 2009, 15, 4343
14. A. Procopio, G. Das, M. Nardi, M. Oliverio, L. Pasqua, ChemSusChem 2008, 1, 916
15. K. Iwanami, J.-C. Choi, B. Lu, T. Sakakura, H. Yasuda, Chem. Commun. 2008, 1002
16. W. K. Cho, J. K. Lee, S. M. Kang, Y. S. Chi, H.-S. Lee, I. S. Chio, Chem. Eur. J. 2007, 13, 6351
17. S. Huh, H.-T. Chen, J. W. Wiench, M. Pruski, V. S.-Y. Lin, Angew. Chem. 2005, 117, 1860
18. Angew. Chem. Int. Ed. 2005, 44, 1826
19. K. Yamaguchi, T. Imago, Y. Ogasawara, J. Kasai, M. Kotani, N. Mizuno, Adv. Synth. Catal. 2006, 348, 1516
20. B. Karimi, L. Ma'Mani, Org. Lett. 2004, 6, 4813
21. K. Higuchi, M. Onaka, Y. Izumi, Bull. Chem. Soc. Jpn. 1993, 66, 2016.
22. N. H. Khan, R. I. Kureshy, S. H. R. Abdi, S. Agrawal, R. V. Jasra, Coord. Chem. Rev. 2008, 252, 593
23. Y. Shen, X. Feng, Y. Li, G. Zhang, Y. Jiang, Eur. J. Org. Chem. 2004, 129
24. H. Deng, M. P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2002, 114, 1051
25. Angew. Chem. Int. Ed. 2002, 41, 1009
26. O. R. Evans, H. L. Ngo, W. Lin, J. Am. Chem. Soc. 2001, 123, 10395
27. Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641
28. Z. Zhang, K. M. Lippert, H. Hausmann, M. Kotke, P. R. Schreiner, J. Org. Chem. 2011, 76, 9764
29. C. Lv, Q. Cheng, D. Xu, S. Wang, C. Xia, W. Sun, Eur. J. Org. Chem. 2011, 3407
30. D. Dang, P. Wu, C. He, Z. Xie, C. Duan, J. Am. Chem. Soc. 2010, 132, 14321.
31. C. L. Hill, C. M. Prosser-McCartha, Coord. Chem. Rev. 1995, 143, 407
32. T. Okuhara, N. Mizuno, M. Misono, Adv. Catal. 1996, 41, 113
33. R. Neumann, Prog. Inorg. Chem. 1998, 47, 317
34. Thematic issue on polyoxometalates:, C. L. Hill, Chem. Rev. 1998, 98, 1-390
35. I. V. Kozhevnikov, Catalysis by Polyoxometalates, Wiley, Chichester, 2002.
36. Y. Ogasawara, S. Itagaki, K. Yamaguchi, N. Mizuno, ChemSusChem 2011, 4, 519.
37. C. Boglio, G. Lemiére, B. Hasenknopf, S. Thorimbert, E. Lacôte, M. Malacria, Angew. Chem. 2006, 118, 3402
38. Angew. Chem. Int. Ed. 2006, 45, 3324
39. C. Boglio, K. Micoine, P. Rémy, B. Hasenknopf, S. Thorimbert, E. Lacôte, M. Malacria, C. Afonso, J.-C. Tabet, Chem. Eur. J. 2007, 13, 5426
40. N. Dupré, P. Rémy, K. Micoine, C. Boglio, S. Thorimbert, E. Lacôte, B. Hasenknopf, M. Malacria, Chem. Eur. J. 2010, 16, 7256
41. M. Bosco, S. Rat, N. Dupré, B. Hasenknopf, E. Lacôte, M. Malacria, P. Rémy, J. Kovensky, S. Thorimbert, A. Wadouachi, ChemSusChem 2010, 3, 1249.
42. Y. Kikukawa, K. Yamaguchi, N. Mizuno, Angew. Chem. 2010, 122, 6232
43. Angew. Chem. Int. Ed. 2010, 49, 6096
44. Y. Kikukawa, Y. Kuroda, K. Yamaguchi, N. Mizuno, Angew. Chem. 2012, DOI:; Angew. Chem. Int. Ed. 2012, DOI:.
45. G. C. Pimentel, A. L. McClellan, The Hydrogen Bond, W. H. Freeman and Company, San Francisco, 1960.
46. F. Xin, M. T. Pope, Inorg. Chem. 1996, 35, 5693.
47. R. D. Peacock, T. J. R. Weakley, J. Chem. Soc. A 1971, 1836
48. K.-C. Kim, M. T. Pope, G. J. Gama, M. H. Dickman, J. Am. Chem. Soc. 1999, 121, 11164
49. R. C. Howell, F. G. Perez, S. Jain, W. DeW. Horrocks, Jr., A. L. Rheingold, L. C. Francesconi, Angew. Chem. 2001, 113, 4155
50. Angew. Chem. Int. Ed. 2001, 40, 4031
51. H. Naruke, T. Yamase, Bull. Chem. Soc. Jpn. 2002, 75, 1275
52. X. Fang, T. Anderson, W. A. Neiwert, C. L. Hill, Inorg. Chem. 2003, 42, 8600
53. X. Fang, T. M. Anderson, C. Benelli, C. L. Hill, Chem. Eur. J. 2005, 11, 712
54. M. Barsukova, M. H. Dickman, E. Visser, S. S. Mal, U. Kortz, Z. Anorg. Allg. Chem. 2008, 634, 2423
55. R. Khoshnavazi, R. Sadeghi, L. Bahrami, Polyhedron 2008, 27, 1855
56. R. Khoshnavazi, S. Gholamyan, J. Coord. Chem. 2010, 63, 3365
57. M. Ibrahim, S. S. Mal, B. S. Bassil, A. Banerjee, U. Kortz, Inorg. Chem. 2011, 50, 956.