A chiral menthyl cyclopentadienyl molybdenum tricarbonyl chloro complex: Synthesis, heterogenization on MCM-41/MCM-48 and application in olefin epoxidation catalysis

Journal of Organometallic Chemistry

Volumn 691, Issue 14, 2006, Pages 3137-3145

  Abrantes, Marta ^a   Sakthivel, Ayyamperumal ^a   Romão, Carlos C ^a   Kühn, Fritz E ^a,b  

^a EAN ^*  (Portugal)

^b INSTITUTO TECNOLÓGICO E NUCLEAR   (Portugal)

Author keywords

Epoxidation; Grafting; Mesoporous materials; Molybdenum; Organometallic complexes

Indexed keywords

ADSORPTION ISOTHERMS; CARBON TETRACHLORIDE; CATALYSIS; CATALYSTS; COMPLEXATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDRIDES; MESOPOROUS MATERIALS; NUCLEAR MAGNETIC RESONANCE; OLEFINS; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION ANALYSIS;

EPOXIDATION CATALYSIS; GRAFTING; HETEROGENIZATION; ORGANOMETALLIC COMPLEXES;

MOLYBDENUM COMPOUNDS;

EID: 33745119778     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.03.037     Document Type: Article

References (74)

1. Mijs W.J., and De Jonge C.R.H.I. Organic Synthesis by Oxidation with Metal Compounds (1996), Plenum Press, New York
2. Reddy C.C., Hamilton G.A., and Madyashta K.M. Biological Oxidation System (1990), Academic Press, San Diego, CA
3. Jacobsen E.N., Zhang W., and Güler M.L. J. Am. Chem. Soc. 113 (1991) 6703
4. Jacobsen E.N., Zhang W., Muci A.R., Ecker J.R., and Deng L. J. Am. Chem. Soc. 113 (1991) 7063
5. Zhang W., and Jacobsen E.N. J. Org. Chem. 56 (1996) 2296
6. Palucki M., McCormick G.J., and Jacobsen E.N. Tetrahedron Lett. 36 (1995) 5457
7. Mukaiyama T., Yamada T., Nagata T., and Imagawa K. Chem. Lett. (1993) 327
8. Adam W., Jeko J., Levai A., Nemes C., Patonay T., and Sebok P. Tetrahedron Lett. 36 (1995) 3666
9. Pietikäinen P. Tetrahedron Lett. 40 (1999) 1001
10. For a Comprehensive Overview see for example. Bäckvall J.E. Modern Oxidation Methods (2004), Wiley-VCH, Weinheim
11. Sheldon R.A. J. Mol. Catal. 7 (1980) 107
12. Thiel W.R., and Priermeier T. Angew. Chem., Int. Ed. Engl. 34 (1995) 1737
13. Thiel W.R. J. Mol. Catal. A: Chem. 117 (1997) 449
14. Kühn F.E., Lopes A.D., Santos A.M., Herdtweck E., Haider J.J., Romão C.C., and Santos A.G. J. Mol. Catal. A: Chem. 151 (2000) 147
15. Abrantes M., Valente A.A., Pillinger M., Gonçalves I.S., Rocha J., and Romão C.C. Inorg. Chem. Commun. 5 (2002) 1069
16. Abrantes M., Valente A.A., Pillinger M., Gonçalves I.S., Rocha J., and Romão C.C. J. Catal. 209 (2002) 237
17. Nunes C.D., Valente A.A., Pillinger M., Fernandes A.C., Romão C.C., Rocha J., and Gonçalves I.S. J. Mater. Chem. 12 (2002) 1735
18. Fuerte A., Iglesias M., Sanchez F., and Corma A. J. Mol. Catal. A: Chem. 211 (2004) 227
19. Herrmann W.A., Haider J.J., Fridgen J., Lobmaier G.M., and Spiegler M. J. Organomet. Chem. 603 (2000) 69
20. Bellemin-Caponnaz S., Coleman K.S., and Osborn J.A. Polyhedron 18 (1999) 273
21. Cross R.J., Newman P.D., Peacock R.D., and Stirling D. J. Mol. Catal. A: Chem. 144 (1999) 273
22. Kühn F.E., Santos A.M., Lopes A.D., Gonçalves I.S., Rodriguez-Borges J.E., Pillinger M., and Romão C.C. J. Organomet. Chem. 621 (2001) 207
23. Valente A.A., Gonçalves I.S., Lopes A.D., Rodriguez-Borges J.E., Pillinger M., Romão C.C., Rocha J., and Garci{dotless}́a-Mera X. New. J. Chem. 25 (2001) 959
24. Gonçalves I.S., Santos A.M., Romão C.C., Lopes A.D., Rodriguez-Borges J.E., Pillinger M., Ferreira P., Rocha J., and Kühn F.E. J. Organomet. Chem. 626 (2001) 1
25. Xia Q.H., Ge H.Q., Ye C.P., Liu Z.M., and Su K.X. Chem. Rev. 105 (2005) 1603
26. Kühn F.E., Zhao J., and Herrmann W.A. Tetrahedron Asymm. 16 (2005) 3469
27. Zhao J., Zhou X.-G., Santos A.M., Herdtweck E., Romão C.C., and Kühn F.E. Dalton Trans. (2003) 3736
28. Zhou X.-G., Zhao J., Santos A.M., and Kühn F.E. Z. Naturforsch. B 596 (2004) 1223
29. Fridgen J., Herrmann W.A., Eickerling G., Santos A.M., and Kühn F.E. J. Organomet. Chem. 689 (2004) 2752
30. Abrantes M., Santos A.M., Mink J., Kühn F.E., and Romão C.C. Organometallics 22 (2003) 2112
31. Trost M.K., and Bergman R.G. Organometallics 10 (1991) 1172
32. Martins A.M., Romão C.C., Abrantes M., Azevedo M.C., Cui J., Dias A.R., Duarte M.T., Lemos M.A., Lorenço T., and Poli R. Organometallics 24 (2005) 2582
33. Valente A.A., Seixas J.D., Gonçalves I.S., Abrantes M., Pillinger M., and Romão C.C. Catal. Lett. 101 (2005) 127
34. Faller J.W., and Ma Y. Organometallics 7 (1988) 559
35. J. Organomet. Chem. 368 (1989) 45
36. Zhao J., Santos A.M., Herdtweck E., and Kühn F.E. J. Mol Catal. A, Chem. 222 (2004) 265
37. Giardello M.A., Ponticello V.P., Brard L., Sabat M., Rheingold A.L., Stern C.L., and Marks T.J. J. Am. Chem. Soc. 116 (1994) 10212
38. Cesarotti E., Kagan H.B., Goddard R., and Krüger C. J. Organomet. Chem. 162 (1978) 297
39. Schumann H., Stenzel O., Dechert S., Girgdies F., and Haltermann R.L. Organometallics 20 (2001) 5360
40. Schumann H., Stenzel O., Dechert S., Girgdies F., and Haltermann R.L. Organometallics 20 (2001) 2155
41. Schumann H., Stenzel O., Dechert S., Girgdies F., Blum J., Gelman D., and Haltermann R.L. Eur. J. Inorg. Chem. (2002) 211
42. Schumann H., Stenzel O., Girgdies F., and Haltermann R.L. Organometallics 20 (2001) 1743
43. Gutnov A., Heller B., Fischer C., Drexler H.-J., Spannenberg A., Sundermann B., and Sundermann C. Angew. Chem., Int. Ed. 43 (2004) 3795
44. Zhang X., Prosenc M.H., Meyer-Friedrichsen T., and Heck J. Eur. J. Inorg. Chem. (2003) 313
45. Douglass M.R., Ogasawara M., Hong S., Metz M.V., and Marks T.J. Organometallics 21 (2002) 283
46. Beagley P., Davies P.J., Blacker A.J., and White C. Organometallics 21 (2002) 5852
47. Corma A., and Garcia H. Chem. Rev. 102 (2002) 3837
48. de Vos D.E., Dams M., Sels B.F., and Jacobs P.A. Chem. Rev. 102 (2002) 1085
49. Leadbeater N.E., and Marco M. Chem. Rev. 102 (2002) 3217
50. Bianchini C., and Barbaro P. Topics Catal. 19 (2002) 17
51. Li C. Catal. Rev.-Sci. Eng. 46 (2004) 419
52. Sakthivel A., Zhao J., Hanzlik M., and Kühn F.E. Dalton Trans. (2004) 3338
53. Sakthivel A., Zhao J., Hanzlik M., Chiang A.S.T., Herrmann W.A., and Kühn F.E. Adv. Syn. Catal. 347 (2005) 473
54. Sakthivel A., Zhao J., Hanzlik M., Raudaschl-Sieber G., and Kühn F.E. Appl. Catal. A; Gen. 281 (2005) 267
55. Sakthivel A., Zhao J., and Kühn F.E. Catal. Lett. 102 (2005) 114
56. Sakthivel A., Zhao J., and Kühn F.E. Stud. Surf. Sci. Catal. 156 (2005) 237
57. Sakthivel A., Zhao J., Raudaschl-Sieber G., and Kühn F.E. J. Organomet. Chem. 690 (2005) 5105
58. Sakthivel A., Hijazi A.K., Hanzlik M., Chiang A.S.T., and Kühn F.E. Appl. Catal. A-Gen. 294 (2005) 161
59. Gago S., Pillinger M., Valente A.A., Santos T.M., Rocha J., and Gonçalves I.S. Inorg. Chem. 43 (2004) 5422
60. Abrantes M., Gago S., Valente A.A., Pillinger M., Gonçalves I.S., Santos T.M., Rocha J., and Romão C.C. Eur. J. Inorg. Chem. (2004) 4914
61. Jia M., Seifert A., and Thiel W.R. Chem. Mater. 15 (2003) 2174
62. J. Catal. 221 (2004) 319
63. Jia M.J., Seifert A., Berger M., Giegengack H., Schulze S., and Thiel W.R. Chem. Mater. 16 (2004) 877
64. Nunes C.D., Valente A.A., Pillinger M., Rocha J., and Gonçalves I.S. Chem. Eur. J. 9 (2003) 4380
65. Inorg. Chem. Commun. 6 (2003) 1228
66. Kresge C.T., Leonowicz M.E., Roth W.J., Vartuli J.C., and Beck J.S. Nature 359 (1992) 710
67. Ryoo R., Joo S.H., and Kim J.M. J. Phys. Chem. B 103 (1999) 7435
68. Sakthivel A., and Selvam P. J. Catal. 211 (2002) 134
69. Goldman A.S., and Tyler D.R. Organometallics 3 (1984) 449
70. Abugideiri F., and Poli R. In: Herrmann W.A. (Ed). Synthetic Methods of Organometallic and Inorganic Chemistry vol . 8 (1997), Georg Thieme, Stuttgart 103
71. Le Gall J.-Y., Kubicki M.M., and Petillon F.Y. J. Organomet. Chem. 221 (1981) 287
72. van Vliet M.C.A., Arends I.W.C.E., and Sheldon R.A. Chem. Comm. (1999) 821
73. Sing K.S.W., Everett D.H., Haul R.A.W., Moscow L., Pierotti R.A., Rouquerol T., and Siemienewska T. Pure Appl. Chem. 57 (1985) 603
74. Kim G.J., and Park D.W. Catal. Today 63 (2000) 537