Ionic liquid [omim][PF6] as an efficient and recyclable reaction media for the cyanosilylation of aldehydes without Lewis acid or any special activation

Tetrahedron Letters

Volumn 46, Issue 17, 2005, Pages 3137-3139

  Shen, Zhi Liang ^b   Ji, Shun Jun ^b   Loh, Teck Peng ^a,b  

^a Nanyang Technological University   (Singapore)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

Cyanohydrins; Cyanosilylation; Ionic liquid; Recycle; TMSCN; omim PF6

Indexed keywords

ALDEHYDE DERIVATIVE; FLUORINE DERIVATIVE; LEWIS ACID;

ARTICLE; CHEMICAL REACTION; CYANATION; LIQUID; RECYCLING; SILYLATION;

EID: 15944422923     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.177     Document Type: Article

References (51)

1. B.R. Matthews, H. Gountzos, W.R. Jackson, and K.G. Watson Tetrahedron Lett. 30 1989 5157 5158
2. W.R. Jackson, H.A. Jacobs, G.S. Jayatilake, B.R. Matthews, and K.G. Watson Aust. J. Chem. 43 1990 2045
3. W.R. Jackson, H.A. Jacobs, B.R. Matthews, G.S. Jayatilake, and K.G. Watson Tetrahedron Lett. 31 1990 1447 1450
4. T. Ziegler, B. Horsch, and F. Effenberger Synthesis 7 1990 575 578
5. F. Effenberger, and U. Stelzer Angew. Chem., Int. Ed. Engl. 30 1991 873
6. P. Zandbergen, J. Brussee, A. Van der Gen, and C.G. Kruse Tetrahedron: Asymmetry 3 1992 769 774
7. Synthesis of pharmaceutical: K.G. Watson, Y.M. Fung, M. Gredley, G.J. Bird, W.R. Watson, H. Gountzos, and B.R. Matthews J. Chem. Soc., Chem. Commun. 15 1990 1018 1019
8. For a recent review: M. North Synlett 11 1993 807 820 and references cited therein
9. F.-X. Chen, X.-M. Feng, B. Qin, G.-L. Zhang, and Y.-Z. Jiang Synlett 4 2003 558 560
10. Y.-C. Shen, X.-M. Feng, Y. Li, G.-L. Zhang, and Y.-Z. Jiang Tetrahedron 59 2003 5667 5675
11. T.-P. Loh, K.-C. Xu, D.S.C. Ho, and K.-Y. Sim Synlett 1998 369 370
12. Z.-X. Bian, H.-Y. Zhao, and B.-G. Li Polyhedron 22 2003 1523 1528
13. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, and A.R. Prasad Tetrahedron Lett. 43 2002 9703 9706
14. V.K. Singh, P. Saravanan, and R. Vijaya Anand Tetrahedron Lett. 39 1998 3823 3824
15. H.S. Wilkinson, P.T. Grover, C.P. Vandenbossche, R.P. Bakale, N.N. Bhongle, S.A. Wald, and C.H. Senanayake Org. Lett. 3 2001 553 556
16. M. Bandini, P.G. Cozzi, P. Melchiorre, and A. Umani-Ronchi Tetrahedron Lett. 42 2001 3041 3043
17. C. Baleizao, B. Gigante, H. Garcia, and A. Corma Tetrahedron Lett. 44 2003 6813 6816 and references cited therein
18. Y. Hamashima, D. Sawada, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 121 1999 2641 2642
19. Y. Hamsahima, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 122 2000 7412 7413
20. K. Yabu, S. Masumoto, S. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D.P. Curran, and M. Shibasaki J. Am. Chem. Soc. 123 2001 9908 9909
21. Y. Hamashima, M. Kanai, and M. Shibasaki Tetrahedron Lett. 42 2001 691 694
22. K. Yabu, S. Masumoto, M. Kanai, D.P. Curran, and M. Shibasaki Tetrahedron Lett. 43 2002 2923 2926
23. H. Deng, M.P. Isler, M.L. Snapper, and A.H. Hoveyda Angew. Chem., Int. Ed. 41 2002 1009 1012
24. J. Casas, C. Nájera, J.M. Sansano, and J.M. Saá Org. Lett. 4 2002 2589 2592
25. F.-X. Chen, X.-M. Feng, B. Qin, G.-L. Zhang, and Y.-Z. Jiang Org. Lett. 5 2003 949 952
26. Y.-C. Shen, X.-M. Feng, G.-L. Zhang, and Y.-Z. Jiang Synlett 8 2002 1353 1355
27. Y.-C. Shen, X.-M. Feng, Y. Li, G.-L. Zhang, and Y.-Z. Jiang Eur. J. Org. Chem. 1 2004 129 137
28. D.H. Ryu, and E.J. Corey J. Am. Chem. Soc. 126 2004 8106 8107
29. S.K. Tian, R. Hong, and L. Deng J. Am. Chem. Soc. 125 2003 9900 9901 and references cited therein
30. Review articles: R.A. Sheldon Chem. Commun. 2001 2399 2407
31. C.M. Gordon Appl. Catal. A: Gen. 222 2001 101 117
32. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772 3789
33. J.D. Holbrey, and K.R. Seddon Clean Prod. Processes 1 1999 223 236
34. T. Welton Chem. Rev. 99 1999 2071 2084
35. H. Zhao, and S.V. Malhotra Aldrichim. Acta 35 2002 75 83
36. C.E. Song Chem. Commun. 9 2004 1033 1043
37. For example, see: L.A. Blanchard, D. Hancu, E.J. Beckman, and J.F. Brennecke Nature 399 1999 28 29
38. R.A. Brown, P. Pollet, E. Mckoon, C.A. Eckert, C.L. Liotta, and P.G. Jessop J. Am. Chem. Soc. 123 2001 1254 1255
39. W. Leitner Nature 423 2003 930 931
40. X.-F. Yang, M.-W. Wang, and C.-J. Li Org. Lett. 5 2003 657 660
41. T.-P. Loh, L.-C. Feng, H.-Y. Yang, and J.-Y. Yang Tetrahedron Lett. 43 2002 8741 8743
42. S.-L. Chen, S.-J. Ji, and T.-P. Loh Tetrahedron Lett. 45 2004 375 377
43. S.-L. Chen, S.-J. Ji, and T.-P. Loh Tetrahedron Lett. 44 2003 2405 2408
44. S.-J. Ji, M.-F. Zhou, D.-G. Gu, S.-Y. Wang, and T.-P. Loh Synlett 13 2003 2077 2079
45. J. Lu, S.-J. Ji, R. Qian, J.-P. Chen, Y. Liu, and T.-P. Loh Synlett 3 2004 534 536
46. S.-J. Ji, M.-F. Zhou, D.-G. Gu, Z.-Q. Jiang, and T.-P. Loh Eur. J. Org. Chem. 2004 1584 1587
47. S.-J. Ji, Z.-Q. Jiang, J. Lu, and T.-P. Loh Synlett 5 2004 831 835
48. G.W. Kabalka, G. Dong, and B. Venkataiah Org. Lett. 5 6 2003 893 895
49. J. Dupont, S.M. Silva, and R.F. De Souza Catal. Lett. 77 2001 131 133
50. J.S. Yadav, B.V.S. Reddy, C.S. Reddy, and K. Rajasekhar J. Org. Chem. 68 2003 2525 2527
51. 7NO 133.0528, found 133.0554