Bis(pyridylimino)isoindolato-iridium complexes as epoxidation catalysts for alkenes

Organometallics

Volumn 30, Issue 3, 2011, Pages 379-382

  Camerano, José A ^a   Sämann, Christoph ^a   Wadepohl, Hubert ^a   Gade, Lutz H ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ACTIVITY; ELECTRON-RICH OLEFINS; EPOXIDATION CATALYSTS; HIGH YIELD; IRIDIUM COMPLEX; OXIDIZING AGENTS; PYRIDYL; SODIUM SALT;

CATALYST ACTIVITY; IRIDIUM COMPOUNDS; KETONES; OLEFINS; SALTS;

IRIDIUM;

EID: 79751469454     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1010116     Document Type: Article

References (74)

1. Rhodium Catalyzed Organic Reactions; Edwards, S. A., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
2. Iridium Complexes in Organic Synthesis; Oro, L. A., Claver, C., Eds.; Wiley-VCH: Weinheim, Germany, 2009.
3. De Vries, J.-G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation; Wiley-VCH: Weinheim, Germany, 2007.
4. Brodzky, D.; Denise, B.; Pannetier, G. J. Mol. Catal. 1977, 2, 149
5. Matsumoto, T.; Mizoroki, T.; Ozaki, A. J. Catal. 1978, 51, 96
6. Foster, D. Inorg. Chem. 1972, 11, 473
7. Handgraff, J.-W.; Reek, J. N. H.; Meijer, E. J. Organometallics 2003, 22, 3150
8. Spogliarich, R.; Farnetti, E.; Kaspar, J.; Graziani, M.; Cesarotti, E. J. Mol. Catal. 1989, 50, 19
9. Spogliarich, R.; Vidotto, S.; Farnetti, E.; Graziani, M.; Verma Gulati, N. Tetrahedron: Asymmetry 1989, 45, 5703
10. Zhang, X.; Kumobayashi, H.; Tayaka, H. Tetrahedron: Asymmetry 1994, 5, 1179
11. Maillet, C.; Praveen, T.; Janvier, P.; Minguet, S.; Evain, M.; Saluzzo, C.; Tommasino, M. L.; Bujoli, B. J. Organomet. Chem. 2002, 67, 8191
12. Blaser, H.-U.; Buser, H.-P.; Häusel, R.; Jalett, H.-P.; Spindler, F. J. Organomet. Chem. 2001, 621, 34
13. Woodmansee, D. H.; Müller, M.-A.; Neuburger; Pfaltz, A. Chem. Sci. 2010, 1, 72
14. Baeza, A.; Pfaltz, A. Chem. Eur. J. 2010, 16, 4003
15. Schrems, M. G.; Pfaltz, A. Chem. Commun 2009, 6210
16. Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391
17. Chakka, S. K.; Peters, B. K.; Andresson, P. G.; Maguire, G. E. M.; Kruger, H. G.; Govender, T. Tetrahedron: Asymmetry 2010, 21, 2295
18. Verendel, J. H.; Zhou, T.; Li, J.-Q.; Paptchikhine, A.; Lebedev, O.; Andersson, P. G. J. Am. Chem. Soc. 2010, 132, 8880
19. Recent reviews: Takeuchi, R.; Kezuka, S. Synthesis 2006, 3349
20. Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun 2007, 675
21. Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461
22. Recent reviews: Ishii, Y.; Sakaguchi, S. Bull. Chem. Soc. Jpn. 2004, 77, 909
23. Fujita, K.; Yamaguchi, R. Synlett 2005, 560 See also. Casalnuovo, A. L.; Calabrese, J.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738
24. Togni, A.; Dorta, R.; Köllner, C.; Pioda, G. Pure Appl. Chem. 1998, 70, 1477
25. Field, L. S.; Messerle, B. A.; Wren, S. L. Organometallics 2003, 22, 4393
26. Carter, C. A. G.; Vogels, C. M.; Harrison, D. J.; Gagnon, M. K. J.; Norman, D. W.; Langler, R. F.; Baker, R. T.; Westcott, S. A. Organometallics 2001, 20, 2130
27. Takeuchi, R. Synlett 2002, 1954
28. Shibata, T.; Tsuchikama, K. Chem. Commun. 2005, 6017
29. Jeong, N.; Kim, D. H.; Choi, J. H. Chem. Commun. 2004, 1134
30. Carmona, D.; Lamata, M. P.; Viguri, F.; Rodriguez, R.; Oro, L. A.; Lahoz, F. J.; Balana, A. I.; Tejero, T.; Merino, P. J. Am. Chem. Soc. 2005, 127, 13386
31. See for example: Esteruelas, M. A.; Lahoz, F. J.; Onñate, E.; Oro, L. A.; Rodriguez, L. Organometallics 1996, 15, 823
32. Klei, S. R.; Tilley, T. D.; Bergman, R. G. Organometallics 2002, 21, 4648
33. Cipot, J.; McDonald, R.; Ferguson, M. J.; Schatte, G.; Straditto, M. Organometallics 2007, 26, 594
34. Krogh-Jespersen, K.; Czerw, M.; Summa, N.; Renkema, K. B.; Achord, P. A.; Goldman, A. S. J. Am. Chem. Soc. 2002, 124, 11404
35. Göttker-Schnetmann, I.; White, P.; Brookhart, M. J. Am. Chem. Soc. 2004, 126, 1804
36. Goldman, A. S.; Roy, A. H.; Huang, Z.; Ahuja, R.; Schinsli, W.; Brookhart, M. Science 2006, 312, 257 and references cited therein.
37. The most widely developed methods for the epoxidation of olefins involve complexes of the early and middle transition metals and some late transition metals such as palladium and copper: Adolfsson, H. In Modern Oxidation Methods, 1 st ed.; Bäckvall, J.-E., Ed.; Wiley: Weinheim, Germany, 2004.
38. Morvillo, A.; Bressan, M. J. Mol. Catal. 1986, 37, 63
39. Lyons, J. E.; Turner, J. O. J. Org. Chem. 1972, 37, 2881
40. Lyons, J. E.; Turner, J. O. Tetrahedron Lett. 1972, 2903
41. Fusi, A.; Ugo, R.; Fox, F.; Pasini, A.; Cenisi, S. J. Organomet. Chem. 1971, 26, 417
42. Albrecht, M.; van Koten, G. Angew. Chem. 2001, 113, 3866;
43. Angew. Chem., Int. Ed. 2001, 40, 3750.
44. van der Boom, M.; Milstein, D. Chem. Rev. 2003, 103, 1759
45. Siegl, W. O. J. Org. Chem. 1977, 42, 1872
46. Siegl, W. O. Inorg. Nucl. Chem. Lett. 1974, 10, 825
47. Chavez, F. A.; Mascharak, P. K. Acc. Chem. Res. 2000, 33, 539
48. Farinas, E. T.; Nguyen, C. V.; Mascharak, P. K. Inorg. Chim. Acta 1997, 263, 17
49. Saussine, L.; Brazi, E.; Robine, A.; Mimoun, H.; Fischer, J.; Weiss, R. J. Am. Chem. Soc. 1985, 107, 3534
50. Krimm, H. British Patent 743, 940.
51. Siggelkow, B.; Meder, M. B.; Galka, C. H.; Gade, L. H. Eur. J. Inorg. Chem. 2004, 3424
52. Langlotz, B. K.; Lloret-Fillol, J.; Gross, J. H.; Wadepohl, H.; Gade, L. H. Chem. Eur. J. 2008, 14, 10267
53. Meder, M. B.; Gade, L. H. Eur. J. Inorg. Chem. 2004, 2716
54. Meder, M. B.; Siggelkow, B. A.; Gade, L. H. Z. Anorg. Allg. Chem. 2004, 630, 1962
55. Horner, L.; Jürgens, E. Chem. Ber. 1957, 90, 2184
56. Davis, F. A.; Lamendola, J., Jr.; Nadir, U. K.; Kluger, E. V.; Sedergran, T. C.; Panunto, T. W.; Billmers, R., Jr.; Turchi, I. J.; Watson, W. H.; Chen, J. S.; Kimura, M. J. Am. Chem. Soc. 1980, 102, 2000
57. Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703
58. Davis, F. A.; Abdul-Malik, N. F.; Awad, S. B.; Harakal., M. E. Tetrahedron Lett. 1981, 917
59. Wilbuer, A.; Vlecken, D. H.; Schmitz, D. J.; Kräling, K.; Harms, K.; Bagowski, C. P.; Meggers, E. Angew. Chem., Int. Ed. 2010, 49, 3839
60. 2, (18d, 18e) all non-hydrogen atoms anisotropic, hydrogen atoms at calculated positions (refined riding), except those of the cod methyne groups (refined with d (CH) restrained equal). Sheldrick, G. M. SADABS; Bruker AXS, 2004-2008.
61. Sheldrick, G. M. SHELXS-97; University of Göttingen, Göttingen, Germany, 1997.
62. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112
63. Sheldrick, G. M. SHELXL-97; University of Göttingen, Göttingen, Germany, 1997.
64. Hui-Min, W.; Yu-Hui, W.; Yang, F.; Li-Yi, Z.; Chang-Neng, C.; Zhong-Ning, C. Inorg. Chem. 2010, 49, 2210
65. Langlotz, B. K.; Wadepohl, H.; Gade, L. H. Angew. Chem., Int. Ed. 2008, 47, 4670
66. Bröring, M.; Kleeberg, C; Cónsul-Tejero, E. Eur. J. Inorg. Chem. 2007, 3208
67. Tejel, C.; del Rio, M. P.; Ciriano, M. A.; Reijerse, E. J.; Hartl, F.; Záliš, S.; Hetterscheid, D. G. H.; Tsichlis i Spithas, N.; de Bruin, B. Chem. Eur. J. 2009, 15, 11878
68. Mc Bee, J. L.; Escalada, J.; Tilley, D. T. J. Am. Chem. Soc. 2009, 131, 12703
69. Rohde, J. U.; Kelley, M. R.; Lee, W. E. Inorg. Chem. 2007, 47, 11461
70. Yuan, L. C.; Bruice, T. C. J. Chem. Soc., Chem. Commun. 1985, 868
71. Davis, F. A.; Abdul-Malik, N. F.; Awad, S. B.; Harakal., M. E. Tetrahedron Lett. 1981, 917
72. Murali, M.; Mayilmurugan, R.; Paliniandavar, M. Eur. J. Inorg. Chem. 2009, 22, 3238
73. Roy, P.; Nandi, M.; Manassero, N.; Riccó, M.; Mazzani, M.; Bhaumik, A.; Banerjee, P. Dalton Trans. 2009, 9543
74. McDonald, A. R.; Franssen, N.; van Klink, G. P. M.; van Koten, G. J. Organomet. Chem. 2009, 14, 2153