Syntheses of monomeric iron and manganese complexes using bulky tripodal ligands: Catalytic alkene epoxidations

Journal of Organometallic Chemistry

Volumn 601, Issue 1, 2000, Pages 57-68

  Chen, Jinyuan ^a   Woo, L Keith ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Catalysis; Epoxidation; Iron; Manganese; Oxidation

Indexed keywords

EID: 0002242082     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00022-X     Document Type: Article

References (67)

1. (a) R.H. Holm, Chem. Rev. 87 (1987) 1401.
2. (b) K.A. Jorgensen, Chem. Rev. 89 (1989) 431.
3. (c) K.B. Sharpless, T.R. Verhoeven, Aldrichim. Acta 12 (1979) 63.
4. (a) A.J. Castellino, T.C. Bruice, J. Am. Chem. Soc. 110 (1988) 158.
5. (b) J.T. Groves, T.E. Nemo, R.S. Myers, J. Am. Chem. Soc. 101 (1979) 1032.
6. (c) E. Guilmet, B. Meunier, Tetrahedron Lett. 21 (1980) 4449.
7. (d) Z.Q. Tian, J.L. Richards, T.G. Traylor, J. Am. Chem. Soc. 117 (1995) 21.
8. (a) W. Zhang, E.N. Jacobsen, J. Org. Chem. 56 (1991) 2296.
9. (b) C.W. Ho, W.C. Cheng, M.C. Cheng, S.M. Peng, K.F. Cheng, C.M. Che, J. Chem. Soc. Dalton Trans. (1996) 405.
10. (a) T. Katsuki, K.B. Sharpless, J. Am. Chem. Soc. 102 (1980) 5974.
11. (b) V.S. Martin, S.S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, K.B. Sharpless, J. Am. Chem. Soc. 103 (1981) 6237.
12. (c) M.G. Finn, K.B. Sharpless, in: J.D. Morrison (Ed.), Asymmetric Synthesis, vol. 5, Academic, New York, 1985, Ch. 8.
13. Vos D.E.D., Bein T. J. Organomet. Chem. 520:1996;195.
14. (a) W.A. Herrmann, R.W. Fischer, D.W. Marz, Angew. Chem. Int. Ed. Engl. 30 (1991) 1638.
15. (b) A.M. Al-Ajlouni, J.H. Espenson, J. Am. Chem. Soc. 117 (1995) 9243.
16. (a) D.C. Heimbrook, R.L. Mulholland, Jr., S.M. Hecht, J. Am. Chem. Soc. 108 (1986) 7839.
17. (b) J. Stubbe, J.W. Kozarich, Chem. Rev. 87 (1987) 1107.
18. (c) D.C. Heimbrook, S.A. Carr, M.A. Mentzer, E.C. Long, S.M. Hecht, Inorg. Chem. 26 (1987) 3835.
19. (a) W. Adam, R. Kumar, T.I. Reddy, M. Renz, Angew. Chem. Int. Ed. Engl. 35 (1996) 880.
20. (b) J.D. Koola, J.K. Kochi, Inorg. Chem. 26 (1987) 908.
21. (c) J.P. Collman, L.S. Hegedus, J.R. Norton, R.G. Finke (Eds.), Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1987.
22. B. Meunier, Bull. Soc. Chim. Fr. (1986) 578.
23. J.-C. Marchon, R. Ramasseul, Synthesis (1989) 389.
24. (a) T. Yamada, T. Takai, O. Rhode, T. Mukaiyama, Bull. Chem. Soc. Jpn. 64 (1991) 2109.
25. (b) T. Mukaiyama, T. Takai, T. Yamada, O. Rhode, Chem. Lett. (1990) 1661.
26. (c) T. Yamada, T. Takai, O. Rhode, T. Mukaiyama, Chem. Lett. (1991) 1.
27. Fdil N., Romane A., Allaoud S., Karim A., Castanet Y., Mortreux A. J. Mol. Catal. A: Chem. 108:1996;15.
28. T. Takai, T. Yamada, T. Mukaiyama, Chem. Lett. (1990) 1657.
29. Takai T., Hata E., Yamada T., Mukaiyama T. Bull. Chem. Soc. Jpn. 64:1991;2513.
30. (a) N. Mizuno, H. Weiner, R.G. Finke, J. Mol. Catal. A: Chem. 114 (1996) 15.
31. (b) O.A. Kholdeeva, V.A. Grigoriev, G.M. Maksimov, M.A. Fedotov, A.V. Golovin, K.I. Zamaraev, J. Mol. Catal. A: Chem. 114 (1996) 123.
32. (a) R. Belal, B. Meunier, J. Mol. Catal. 44 (1988) 187.
33. (b) N. Kitajima, N. Tamura, H. Amagai, H. Fukui, Y. Moro-oka, Y. Mizutani, T. Kitagawa, R. Mathur, K. Heerwegh, C.A. Reed, C.R. Randall, L. Que, Jr., K. Tatsumi, J. Am. Chem. Soc. 116 (1994) 9071.
34. Medina J.C., Gabriunas N., Paez-Mozo E. J. Mol. Catal. A: Chem. 115:1997;233.
35. Anzenbacher P. Jr., Kral V., Jursikova K., Gunterova J., Kasal A. J. Mol. Catal. A: Chem. 118:1997;63.
36. (a) P.S. Traylor, D. Dolphin, T.G. Traylor, J. Chem. Soc. Chem. Commun. (1984) 279.
37. (b) P. Bhyrappa, J.K. Young, J.S. Moore, K.S. Suslick, J. Mol. Catal. A: Chem. 113 (1996) 109.
38. (c) P. Bhyrappa, J.K. Young, J.S. Moore, K.S. Suslick, J. Am. Chem. Soc. 118 (1996) 5708.
39. Gorrell I.B., Parkin G. Inorg. Chem. 29:1990;2452.
40. (a) N. Kitajima, H. Fukui, Y. Moro-oka, J. Chem. Soc. Chem. Commun. (1988) 485.
41. (b) N. Kitajima, M. Ito, H. Fukui, Y. Moro-oka, J. Chem. Soc. Chem. Commun. (1991) 102.
42. Shriver D.F., Drezdon M.A. The Manipulation of Air-Sensitive Compounds. 1986;Wiley-Interscience, New York.
43. Starke K.J. Inorg. Nucl. Chem. 11:1959;77.
44. Saltzman H., Sharefkin J.G. Org. Synth. 5:1973;658.
45. Duan Z., Young V.G. Jr., Verkade J.G. Inorg. Chem. 34:1995;2179.
46. Wilkinson G., Cotton F.A., Birmingham J.M. J. Inorg. Nucl. Chem. 2:1956;95.
47. Schrock R.R., Sturgeoff L.G., Sharp P.R. Inorg. Chem. 22:1983;2801.
48. Bradley D.C., Copperthwaite R.G. Inorg. Synth. 18:1978;112.
49. Ellison J.J., Power P.P., Shoner S.C. J. Am. Chem. Soc. 111:1989;8044.
50. Kol M., Schrock R.R., Kempe R., Davis W.M. J. Am. Chem. Soc. 116:1994;4382.
51. Trofimenko S., Calabrese J.C., Thompson J.S. Inorg. Chem. 26:1987;1507.
52. Cummins C.C., Lee J., Schrock R.R., Davis W.D. Angew. Chem. Int. Ed. Engl. 31:1992;1501.
53. Schrock R.R. Acc. Chem. Res. 30:1997;9. and references therein.
54. (a) J.S. Freundlich, R.R. Schrock, C.C. Cummins, W.M. Davis, J. Am. Chem. Soc. 116 (1994) 6476.
55. (b) C.C. Cummins, R.R. Schrock, W.M. Davis, Inorg. Chem. 33 (1994) 1448.
56. Mahapatra S., Halfen J.A., Wilkinson E.C., Pan G., Wang X., Young V.G. Jr., Cramer C.J., Que L., Tolman W.B. Jr. J. Am. Chem. Soc. 118:1996;11555.
57. Nam W., Kim H.J., Kim S.H., Ho R.Y.N., Valentine J.S. Inorg. Chem. 35:1996;1045.
58. Collman J.P., Brauman J.I., Meunier B., Hayashi T., Kodadek T., Raybuck S.A. J. Am. Chem. Soc. 107:1985;2000.
59. (a) O. Bortolini, B. Meunier, J. Chem. Soc. Perkin Trans. 2 (1984) 167.
60. (b) J.R. Lindsay Smith, P.R. Sleath, J. Chem. Soc. Perkin Trans. 2 (1982) 1009.
61. (c) A.W. Van Der Made, R.J.M. Nolte, J. Mol. Catal. 26 (1984) 333.
62. (d) B. Meunier, E. Guilmet, M.-E. De Carvalho, R. Poilblanc, J. Am. Chem. Soc. 106 (1984) 6688.
63. (e) E. Guilemet, B. Meunier, New J. Chem. (1982) 512.
64. Sheldon R.A., Kochi J.K. Metal-Catalyzed Oxidations of Organic Compounds. 1981;25 Academic Press, New York.
65. Wilkinson G. Comprehensive Coordination Chemistry: The Synthesis, Reaction, Properties and Applications of Coordination Compounds. 1987;1179 Pergamon, Oxford.
66. (a) K. Fujisawa, M. Tanaka, Y. Moro-oka, N. Kitajima, J. Am. Chem. Soc. 116 (1994) 12079.
67. (b) N. Kitajima, K. Fujisawa, C. Fujimoto, Y. Moro-oka, S. Hashimoto, T. Kitagawa, K. Toriumi, K. Tatsumi, A. Nakamura, J. Am. Chem. Soc. 114 (1992) 1277.