Ortho-bis(cyanomercurio)tetrafluorobenzene as a Bidentate lewis acid co-catalyst in the cyanosilylation of benzaldehyde

Organometallics

Volumn 22, Issue 6, 2003, Pages 1275-1280

  King, Julie B ^a   Gabbai, François P ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; BIDENTATE LEWIS ACID; BISCYANOMERCURIOTETRAFLUOROBENZENE; CYANOSILYLATION; ELEMENTAL ANALYSIS;

CATALYSTS; CRYSTAL STRUCTURE; CYANIDES; INFRARED SPECTROSCOPY; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; STRETCHING;

ORGANOMETALLICS;

EID: 0037451050     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020918u     Document Type: Article

References (56)

1. Hawthorne, M. F. Pure Appl. Chem. 1994, 66, 245-254.
2. Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267-276.
3. Chistyakov, A. L.; Stankevich, I. V.; Gambaryan, N. P.; Struchkov, Y. T.; Yanovsky, A. I.; Tikhonova, I. A.; Shur, V. B. J. Organomet. Chem. 1997, 536, 413-424.
4. Vaugeois, J.; Simard, M.; Wuest, J. D. Coord. Chem. Rev. 1995, 145, 55-73.
5. Katz, H. E. Inclusion Compd. 1991, 4, 391.
6. Piers, W. E.; Irvine, G. J.; Williams, V. C. Eur. J. Inorg. Chem. 2000, 10, 2131.
7. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434.
8. (a) Kaufmann, D. E.; Otten, A. Angew. Chem. 1994, 106, 1917-1918.
9. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
10. (c) Beer, P. D.; Smith, D. K. Prog. Inorg. Chem. 1997, 46, 11-96.
11. (d) Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 443-448.
12. (e) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
13. (a) Shur, V. B.; Tikhonova, I. A.; Yanovskii, A. I.; Struchkov, Y. T.; Petrovskii, P. V.; Panov, S. Y.; Furin, G. G.; Vol'pin, M. E. J. Organomet. Chem. 1991, 418, C29-C32.
14. (b) Shur, V. B.; Tikhonova, I. A.; Yanovskii, A. I.; Struchkov, Y. T.; Petrovskii, P. V.; Panov, S. Y.; Furin, G. G.; Vol'pin, M. E. Dokl. Akad. Nauk SSSR 1991, 321, 1002-1004.
15. (c) Shur, V. B.; Tikhonova, I. A.; Dolgushin, F. M.; Yanovsky, A. I.; Struchkov, Y. T.; Volkonsky, A. Y.; Solodova, E. V.; Panov, S. Y.; Petrovskii, P. V.; Vol'pin, M. E. J. Organomet. Chem. 1993, 443, C19-C21.
16. Wuest, J. D.; Zacharie, B. Organometallics 1985, 4, 410-411.
17. Lee, H.; Diaz, M.; Knobler, C. B.; Hawthorne, M. F. Angew. Chem., Int. Ed. 2000, 39, 776-778.
18. Katz, H. E. J. Org. Chem. 1985, 50, 5027-5032.
19. Jia, L.; Yang, X.; Stern, C.; Marks, T. J. Organometallics 1994, 13, 3755-3757.
20. Metz, M. V.; Schwartz, D. J.; Stern, C. L.; Nickias, P. N.; Marks, T. J. Angew. Chem., Int. Ed. 2000, 39, 1312-1316.
21. Köhler, K.; Piers, W. E.; Jarvis, A. P.; Xin, S.; Feng, Y.; Bravakis, A. M.; Collins, S.; Clegg, W.; Yap, G. P. A.; Marder, T. B. Organometallics 1998, 17, 3557-3566.
22. Williams, V. C.; Piers, W. E.; Clegg, W.; Elsegood, M. R. J.; Collins, S.; Marder, T. B. J. Am. Chem. Soc. 1999, 121, 3244-3245.
23. Williams, V. C.; Dai, C.; Li, Z.; Collins, S.; Piers, W. E.; Clegg, W.; Elsegood, M. R. J.; Marder, T. B. Angew. Chem., Int. Ed. 1999, 38, 3695-3698.
24. Williams, V. C.; Irvine, G. J.; Piers, W. E.; Li, Z.; Collins, S.; Clegg, W.; Elsegood, M. R. J.; Marder, T. B. Organometallics 2000, 19, 1619-1621.
25. Sakurai, H. Synlett. 1989, 1-8.
26. Marshall, J. A. Chemtracts-Org. Chem. 1998, 11, 697-712.
27. Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 12, 7920-7921, and reference therein.
28. Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323-4326.
29. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517.
30. Seeberger, P. H.; Haase, W.-C. Chem. Rev. 2000, 100, 4349-4394.
31. Boons, G.-J.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539-4566.
32. Hanessian, S.; Lou, B. Chem. Rev. 2000, 100, 4443-4464.
33. Graybill, T. L.; Casillas, E. G.; Pal, K.; Townsend, C. A. J. Am. Chem. Soc. 1999, 121, 7729-7746.
34. Nishizawa, M.; Yamamoto, H.; Seo, K.; Imagawa, H.; Sugihara, T. Org. Lett. 2002, 4, 1947-1949.
35. Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699.
36. Chen, J.; Sakamoto, K.; Orita, A.; Otera, J. J. Org. Chem. 1998, 63, 9739-9745.
37. Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248-3249.
38. Mukai, C.; Hashizume, S.; Nagami, K.; Hanaoka, M. Chem. Pharm. Bull. 1990, 38, 1509-1512.
39. Sakurai, H.; Sasaki, K.; Hosomi, A. Bull. Chem. Soc. Jpn. 1983, 56, 3195-3196.
40. Miura, K.; Ootsuka, K.; Suda, S.; Nishikori, H.; Hosomi, A. Synlett. 2002, 2, 313-315.
41. Fürstner, A.; Voigtländer, D. Synthesis 2000, 959-969.
42. For the synthesis of 1 see: Massey, A. G.; Al-Jabar, N. A. A.; Humphries, R. E.; Deacon, G. B. J. Organomet. Chem. 1986, 316, 25-39.
43. For the synthesis of 3 see: Chambers, R. D.; Coates, G. E.; Livingstone, J. G.; Musgrave, W. K. R. J. Chem. Soc. 1962, 4367-4371.
44. For the synthesis of 2 and 4 see: Albrecht, H. B.; Deacon, G. B. J. Organomet. Chem. 1973, 57, 77-86.
45. Deacon, G. B.; Tunaley, D. J. Organomet. Chem. 1978, 156, 403-426.
46. Tschinkl, M.; Schier, A.; Riede, J.; Gabbai, F. P. Organometallics 1999, 18, 1747-1753.
47. Tschinkl, M.; Bachman, R. E.; Gabbai, F. P. Organometallics 2000, 19, 2633-2636.
48. Gardinier, J. R.; Gabbai, F. P. J. Chem. Soc., Dalton Trans. 2000, 2861-2865.
49. Beckwith, J. D.; Tschinkl, M. T.; Tsunoda, M.; Picot, A.; Gabbaï, F. P. Organometallics 2001, 20, 3169-3174.
50. Tschinkl, M.; Schier, A.; Riede, J.; Gabbai, F. P. Organometallics 1999, 18, 2040-2042.
51. Nyburg, S. C.; Faerman, C. H. Acta Crystallogr. Sect. B 1985, 41, 274-279.
52. Canty, A. J.; Deacon, G. B. Inorg. Chim. Acta 1980, 45, L225-L227.
53. Pyykkö, P.; Straka, M. Phys. Chem. Chem. Phys. 2000, 2, 2489-2493.
54. Tsunoda, M.; Gabbai, F. P. J. Am. Chem. Soc. 2000, 122, 8335-8336.
55. Martin Tschinkl, Ph.D. Thesis, Technische Universität München, 1999.
56. Goggin, P. L.; Goodfellow, R. J.; Hurst, N. W. J. Chem. Soc., Dalton Trans. 1978, 561-566.