Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study

Journal of the American Chemical Society

Volumn 121, Issue 39, 1999, Pages 9120-9132

  Au, Sze Man ^a   Huang, Jie Sheng ^a   Yu, Wing Yiu ^a   Fung, Wai Hong ^a   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; ALKANE DERIVATIVE; ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE; CUMENE; DEUTERIUM; DICHLOROMETHANE; ETHYLBENZENE; HYDROCARBON; NORBORNENE DERIVATIVE; PORPHYRIN DERIVATIVE; PYRAZOLE DERIVATIVE; RADICAL; RUTHENIUM DERIVATIVE; STILBENE DERIVATIVE; STYRENE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE;

AMIDATION; ARTICLE; CHEMICAL REACTION; HYBRIDIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032830991     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9913481     Document Type: Article

References (72)

1. Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073.
2. (a) Mansuy, D.; Mahy, J.-P.; Dureault, A.; Bedi, G.; Battioni, P. J. Chem. Soc., Chem. Commun. 1984, 1161.
3. (b) Mahy, J.-P.; Bedi, G.; Battioni, P.; Mansuy, D. J. Chem. Soc., Perkin Trans. 2 1988, 1517.
4. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744.
5. (b) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
6. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
7. (d) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
8. (a) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
9. (b) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
10. O'Connor, K. J.; Wey, S.-J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001.
11. Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309.
12. Lai, T.-S.; Kwong, H.-L.; Che, C.-M.; Peng, S.-M. Chem. Commun. 1997, 2373.
13. Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469.
14. Müller, P.; Baud, C.; Jacquier, Y. Tetrahedron 1996, 52, 1543.
15. Au, S.-M.; Fung, W.-H.; Cheng, M.-C.; Che, C.-M.; Peng, S.-M. Chem. Commun. 1997, 1655.
16. Breslow, R.; Gellman, S. H. J. Chem. Soc., Chem. Commun. 1982, 1400.
17. (a) Breslow, R.; Kluttz, R. Q.; Khanna, P. L. Tetrahedron Lett. 1979, 3273.
18. (b) Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728.
19. Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. Tetrahedron Lett. 1988, 29, 1927.
20. Albone, D. P.; Aujla, P. S.; Taylor, P. C. J. Org. Chem. 1998, 63, 9569.
21. Au, S.-M.; Zhang, S.-B.; Fung, W.-H.; Yu, W.-Y.; Che, C.-M.; Cheung, K.-K. Chem. Commun. 1998, 2677.
22. Nägeli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087.
23. (a) Samsel, E. G.; Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1985, 107, 7606.
24. (b) Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1986, 108, 507.
25. (c) Castellino, A. J.; Bruice, T. C. J. Am. Chem. Soc. 1988, 110, 158.
26. (d) Garrison, J. M.; Bruice, T. C. J. Am. Chem. Soc. 1989, 111, 191.
27. (e) Garrison, J. M.; Ostovic, D.; Bruice, T. C. J. Am. Chem. Soc. 1989, 111, 4960.
28. (f) Ostovic, D.; Bruice, T. C. J. Am. Chem. Soc. 1989, 111, 6511.
29. (g) Ostovic, D.; Bruice, T, C. Acc. Chem. Res. 1992, 25, 314.
30. (h) Arasasingham, R. D.; He, G. X.; Bruice, T. C. J. Am. Chem. Soc. 1993, 115, 7985.
31. (i) Groves, J. T.; Gross, Z.; Stern, M. K. Inorg. Chem. 1994, 33, 5065.
32. (j) Finney, N. S.; Pospisil, P. J.; Chang, S.; Palucki, M.; Konsler, R. G.; Hansen, K. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 1720.
33. (k) Linde, C.; Arnold, M.; Norrby, P.; Åkermark, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1723.
34. (l) Linker, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2060.
35. (m) Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948.
36. Wigley, D. E. Prog. Inorg. Chem. 1994, 42, 239.
37. Groves, J. T. Personal communication.
38. Lindler, H.; Dubuis, R. Org. Synth. 1973, 5, 880.
39. (a) Overberger, G. H.; Saunders, J. H. Org. Synth. 1955, 3, 204.
40. (b) Hosokawa, T.; Ohta, T.; Kanagama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758.
41. (c) Wesener, J. R.; Maskau, D.; Günther, H. J. Am. Chem. Soc. 1985, 107, 7307.
42. Abbreviations: TPP = meso-tetraphenylporphyrinato dianion; TTP = meso-tetrakis(p-tolyl)porphyrinato dianion; 4-Cl-TPP = meso-tetrakis-(p-chlorophenyl)porphyrinato dianion; 4-MeO-TPP = meso-tetrakis(p-methoxyphenyl)porphyrinato dianion; OEP = octaethylporphyrinato dianion.
43. Rillema, D. P.; Nagle, J. K.; Barringer, L. F., Jr.; Meyer, T. J. J. Am. Chem. Soc. 1981, 103, 56.
44. PATTY: Beurskens, P. T.; Admiraal, G.; Beurskens, G., Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF program system, Technical Report of the Crystallography Laboratory; University of Nijmegen: The Netherlands, 1992.
45. TeXsan: Crystal Structure Analysis Package; Molecular Structure Corporation: The Woodlands, Texas, 1985 & 1992.
46. Evans, D. F. J. Chem. Soc. 1959, 2003.
47. (a) Groves, J. T.; Quinn, R. Inorg. Chem. 1984, 23, 3844.
48. (b) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
49. (c) Groves, J. T.; Ahn, K.-H. Inorg. Chem. 1987, 26, 3831.
50. (d) Leung, W.-H.; Che, C.-M. J. Am. Chem. Soc. 1989, 111, 8812.
51. (e) Ho, C.; Leung, W.-H.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1991, 2933.
52. Huang, J.-S.; Che, C.-M.; Poon, C.-K. J. Chem. Soc., Chem. Commun. 1992, 161.
53. Leung, W.-H.; Hun, T. S. M.; Hou, H.-W.; Wong, K.-Y. J. Chem. Soc., Dalton Trans. 1997, 237.
54. Au, S.-M.; Fung, W.-H.; Huang, J.-S.; Cheung, K.-K.; Che, C.-M. Inorg. Chem. 1998, 37, 6564.
55. Che, C.-M.; Cheung, W.-C.; Lai, T.-F. Inorg. Chem. 1988, 27, 2801.
56. (a) Ke, M.; Sishta, C.; James, B. R.; Dolphin, D.; Sparapany, J. W.; Ibers, J. A. Inorg. Chem. 1991, 30, 4766.
57. (b) Cheng, S. Y. S.; Rajapakse, N.; Rettig, S. J.; James, B. R. J. Chem. Soc., Chem. Commun. 1994, 2669.
58. (c) Collman, J. P.; Brothers, P. J.; McElwee-White, L.; Rose, E. J. Am. Chem. Soc. 1985, 107, 6110.
59. (d) Collman, J. P.; Brothers, P. J.; McElwee-White, L.; Rose, E.; Wright, L. J. J. Am. Chem. Soc. 1985, 107, 4570.
60. (e) Huang, J.-S.; Che, C.-M.; Li, Z.-Y.; Poon, C.-K. Inorg. Chem. 1992, 31, 1315.
61. 2] (9.68 ppm). See: Sishta, C.; Ke, M.; James, B. R.; Dolphin, D. J. Chem. Soc., Chem. Commun. 1986, 787.
62. Collman, J. P.; Barnes, C. E.; Swepston, P. N.; Ibers, J. A. J. Am. Chem. Soc. 1984, 106, 3500.
63. (a) Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
64. (b) Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J.-M.; Saveant, J.-M. J. Am. Chem. Soc. 1979, 101, 3431.
65. Collin, C. J.; Bowman, N. S. Isotope Effects in Chemical Reactions; Van Nostrand Reinhold: New York, NY, 1970.
66. (a) Schubert, W. M.; Keefe, J. R. J. Am. Chem. Soc. 1972, 94, 559.
67. (b) Yates, K.; McDonald, R. S.; Shapiro, S. A. J. Org. Chem. 1973, 38, 2460.
68. Jiang, X.-K. Acc. Chem. Res. 1997, 30, 283.
69. (a) Che, C.-M.; Leung, W.-H.; Li, C.-K.; Poon, C.-K. J. Chem. Soc., Dalton Trans. 1991, 379.
70. (b) Che, C.-M.; Tang, W.-T., Wong, K.-Y.; Li, C.-K. J. Chem. Soc., Dalton Trans. 1991, 3277.
71. (c) Cheng, W.-C.; Yu, W.-Y.; Li, C.-K.; Che, C.-M. J. Org. Chem. 1995, 60, 6840.
72. Wu, Y.-D.; Wong, C.-L.; Chan, K. W.-K.; Ji, G.-Z.; Jiang X.-K. J. Org. Chem. 1996, 61, 746.