MTO Schiff-base complexes: Synthesis, structures and catalytic applications in olefin epoxidation

Chemistry - A European Journal

Volumn 13, Issue 1, 2007, Pages 158-166

  Zhou, Ming Dong ^a   Zhao, Jin ^b,f,g   Li, Jun ^a   Yue, Shuang ^a   Bao, Chang Nian ^a   Mink, Janos ^c,d   Zang, Shu Liang ^a   Kühn, Fritz E ^b,e  

^a LIAONING UNIVERSITY   (China)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c CHEMICAL RESEARCH CENTER   (Hungary)

^d UNIVERSITY OF PANNONIA   (Hungary)

^e INSTITUTO TECNOLÓGICO E NUCLEAR   (Portugal)

^f NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^g GIST TUM Asia Singapore   (Singapore)

Author keywords

Epoxidation; Homogeneous catalysis; Rhenium; Schiff bases; Structure activity relationships

Indexed keywords

CATALYST ACTIVITY; COMPLEXATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY; ATOMS; CATALYST SELECTIVITY; CATALYSTS; CRYSTALLOGRAPHY; EPOXIDATION; FUNCTIONAL GROUPS; HYDROGEN; REACTION KINETICS; RHENIUM; RHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

CATALYST DECOMPOSITION; EPOXIDATION; HOMOGENEOUS CATALYSIS; SCHIFF BASES; STRUCTURE-ACTIVITY RELATIONSHIPS;

RHENIUM COMPOUNDS; LIGANDS;

CATALYST DECOMPOSITION; CATALYTIC APPLICATIONS; CATALYTIC PERFORMANCE; EPOXIDATION CATALYSTS; HOMOGENEOUS CATALYSIS; SCHIFF BASE COMPLEXES; SCHIFF BASIS; STRUCTURE ACTIVITY RELATIONSHIPS;

EID: 33845942328     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600863     Document Type: Article

References (76)

1. I. R. Beattie, P. J. Jones, Inorg. Chem. 1979, 18, 2318-2319.
2. a) W. A. Herrmann, J. G. Kuchler, J. K. Felixberger, E. Herdtweck, W. Wagner. Angew. Chem. 1988, 100, 420-422:
3. Angew. Chem. Int. Ed. Engl. 1988, 27, 394-396;
4. b) W. A. Herrmann, F. E. Kühn, R. W. Fischer, W. R. Thiel, C. C. Romão, Inorg. Chem. 1992, 31, 4431-4432:
5. c) W. A. Herrmann, R. M. Kratzer, Inorg. Synth. 2002, 33, 110-112.
6. For recent reviews see, for example: a) F. E. Kühn, A.M. Santos, W. A. Herrmann, Dalton Trans. 2005, 2483-2491:
7. b) F. E. Kühn, J. Zhao, W. A. Herrmann. Tetrahedron: Asymmetry 2005, 16, 3469-3479;
8. c) F. E. Kühn, A. Scherbaum, W. A. Herrmann, J. Organomet. Chem. 2004, 689, 4149-4164;
9. d) G. Soldaini, Synlett 2004, 1849-1850.
10. a) W. A. Herrmann, R. W. Fischer, D. W. Marz, Angew. Chem. 1991, 103, 1704-1706;
11. Angew. Chem. Int. Ed. Engl. 1991, 30, 1638-1641;
12. b) W. A. Herrmann, R. W. Fischer, W. Scherer, M. U. Rauch, Angew. Chem. 1993, 105, 1209-1212;
13. Angew. Chem. Int. Ed. Engl. 1993, 32, 1157-1160;
14. c) A. M. Ajlouni, J. H. Espenson, J. Am. Chem. Soc. 1995, 117, 9243-9250:
15. d) A. M. Ajlouni, J. H. Espenson, J. Org. Chem. 1996, 61, 3969-3976;
16. e) F. E. Kühn, A. M. Santos, I. S. Gonçalves, C. C. Romão, A. D. Lopes, Appl. Organomet. Chem. 2001, 15, 43-50.
17. a) M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, Chem. Commun. 1999, 821-822;
18. b) F. E. Kühn, W. A. Herrmann. Struct. Bonding (Berlin) 2000, 97, 213-236;
19. c) J. Iskara, D. Bonnet-Delpon, J. P. Begue, Tetrahedron Lett. 2002, 43, 1001-1003;
20. d) R. Buffon, U. Schuchardt, J. Braz. Chem. Soc. 2003, 14, 347-353;
21. e) R. Saladino, A. A. Andrechi, V. Neri, C. Crestini. Tetrahedron 2005, 61, 1069-1075;
22. f) E. Da Palma Carreiro, G. Yong-En, A. J. Burke, J. Mol. Catal. A 2005, 2483-2491:
23. g) L. M. Gonzalez, A. L. Vila, C. Montes, G. Gelbard, React. Funct. Polym. 2005, 65, 169-181;
24. h) D. Ogrin, A. R. Barron, J. Mol. Catal. A 2006, 244, 267-270;
25. i) S. Gago, J. A. Fernandes, M. Abrantes, F. E. Kühn, P. Ribeiro-Claro, M. Pillinger, T. M. Santos, I. S. Gonçalves, Microporous Mesoporous Mater. 2006, 89, 284-290.
26. a) C. C. Romão, F. E. Kühn, W. A. Herrmann, Chem. Rev. 1997, 97, 3197-3246;
27. b) W. A. Herrmann, F. E. Kühn, Acc. Chem. Res. 1997, 30, 169-180.
28. a) W. A. Herrmann, G. Weichselbaumer, E. Herdtweck. J. Organomet. Chem. 1989, 372, 371-389:
29. b) W. A. Herrmann, J. G. Kuchler, G. Weichselbaumer, E. Herdtweck, P. Kiprof, J. Organomet. Chem. 1989, 372, 351-370.
30. a) W. A. Herrmann, R. W. Fischer, M. U. Rauch, W. Scherer, J. Mol. Catal. 1994, 86, 243-266;
31. b) W. A. Herrmann, F.E. Kühn, M. R. Mattner, G. R. J. Artus, M. Geisberger, J. D. G. Correia, J. Organomet. Chem. 1997, 538, 203-209;
32. c) W. A. Herrmann. F.E. Kühn, M. U. Rauch, J. D. G. Correia, G. Artus, Inorg. Chem. 1995, 34, 2914-2920.
33. a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189-6190;
34. b) C. Coperet, H. Adolfsson, K.B. Sharpless, Chem. Commun. 1997, 1565-1566:
35. c) W. A. Herrmann, H. Ding, R. M. Kratzer, F. E. Kühn, J. J. Haider, R. W. Fischer, J. Organomet. Chem. 1997, 549, 319-322;
36. d) W. A. Herrmann, R. M. Kratzer, H. Ding, W. R. Thiel, H. Glas, J. Organomet. Chem. 1998, 555, 293-295:
37. e) H. Rudier, J. R. Gregorio, B. Denise, J. M. Bregeault. A. Deloffre, J. Mol. Catal. A 1998, 133, 255-265:
38. f) H. Adolfsson, A. Converse, K. B. Sharpless. Tetrahedron Lett. 1999, 40, 3991-3994;
39. g) H. Adolfsson, C. Coperet, J. P. Chiang, A. K. Judin, J. Org. Chem. 2000, 65, 8651-8658.
40. a) F. E. Kühn, A. M. Santos, P. W. Roesky, E. Herdtweck, W. Scherer, P. Gisdakis, I. V. Yudanov, C. di Valentin, N. Rösch, Chem. Eur. J. 1999, 5, 3603-3615;
41. b) P. Ferreira, W. M. Xue, E. Bencze, E. Herdtweck, F. E. Kühn. Inorg. Chem. 2001, 40, 5834-5842;
42. c) A. M. Santos, F. E. Kühn, K. Bruus-Jensen, I. Lucas, C. C. Romão, E. Herdtweck, J. Chem. Soc. Dalton Trans. 2001, 1332-1337:
43. d) J. Mink, G. Keresztury, A. Stirling, W. A. Herrmann, Spectrochim. Acta Part A 1994, 50, 2039-2057.
44. a) M. Nakajima, Y. Sasaki, H. Iwamoto, S. Hashimoto, Tetrahedron Lett. 1998, 39, 87-88;
45. b) W. D. Wang, J. H. Espenson, J. Am. Chem. Soc. 1998, 120, 11335-11341;
46. c) C. D. Nunes, M. Pillinger, A.A. Valente, I. S. Gonçalves, J. Rocha, P. Ferreira, F. E. Kühn, Eur. J. Inorg. Chem. 2002, 1100-1107;
47. d) M. J. Sabater, M.E. Domine, A. Corma, J. Catal. 2002, 210, 192-197;
48. e) E. Da Palma Carreiro, A. J. Burke, M. J. Marcelo Curto, A. J. Teixeira, J. Mol. Catal. A 2004, 217, 69;
49. f) K. Shimura, K. Fujita, H. Kanai, K. Utani, S. Imamura, Appl. Catal. A 2004, 274, 253-257;
50. g) J. J. Haider, R. M. Kratzer, W. A. Herrmann, J. Zhao, F. E. Kühn, J. Organomet. Chem. 2004, 689, 3735-3740;
51. h) S. M. Nabavizadeh, Dalton Trans. 2005, 1644-1648;
52. i) S. M. Nabavizadeh, A. Akbari, M. Rashidi, Eur. J. Inorg. Chem. 2005, 2368-2375;
53. j) S. M. Nabavizadeh, A. Akbari, M. Rashidi. Dalton Trans. 2005, 2423-2427.
54. W. A. Herrmann, J. D. G. Correia, M. U. Rauch, G. R. J. Artus, F. E. Kühn, J. Mol. Catal. A 1997, 118, 33-45.
55. a) P. D. Benny, J. L. Green, H. P. Engelbrecht, C. L. Barnes, S. S. Jurisson, Inorg. Chem. 2005, 44, 2381-2390, and references therein;
56. b) Z.-K. Li, Y. Li, L. Lei, C.-M. Che, X.-G. Zhou, Inorg. Chem. Commun. 2005, 8, 307-309:
57. c) W. A. Herrmann, M. U. Rauch, G. R. J. Artus. Inorg. Chem. 1996, 35, 1988-1991;
58. d) F. E. Kühn, M. U. Rauch, G. M. Lobmaier, G. R. J. Artus, W. A. Herrmann, Chem. Ber./Recueil 1997, 130, 1427-1431.
59. W. A. Herrmann, P. Kiprof, K. Rybdal, J. Tremmel, R. Blom, R. Alberto, J. Behm, R. W. Albach, H. Bock, B. Solouki, J. Mink, D. Lichtenberger, N. E. Gruhn, J. Am. Chem. Soc. 1991, 113, 6527-6537.
60. a) X. G. Zhou, J. Zhao, A. M. Santos, F. E. Kühn, Z. Naturforsch. B 2004, 59, 1223-1228;
61. b) J. Zhao, X. G. Zhou, A.M. Santos, E. Herdtweck, C. C. Romão, F.E. Kühn, Dalton Trans. 2003, 3736-3742.
62. W. A. Herrmann, W. M. Wachter, F. E. Kühn, R. W. Fischer, J. Organomet. Chem. 1998, 553, 443-452.
63. W. A. Herrmann, W. A. Wojtczak, G. R. J. Artus, F. E. Kühn, M. R. Mattner, Inorg. Chem. 1997, 36, 465-471.
64. W. A. Herrmann, P. W. Roesky, M. Wang, W. Scherer. Organometallics 1994, 13, 4531-4535.
65. C. de Méric de Beliefern, W. A. Herrmann, P. Kiprof, C. R. Whitaker, Organometallics 1992, 11, 1072-1081.
66. W. A. Herrmann, F. E. Kühn, P. W. Roesky, J. Organomet. Chem. 1995, 485, 243-251.
67. M. M. Abu-Omar, P. J. Hansen, J. H. Espenson, J. Am. Chem. Soc. 1996, 118, 4966-4974.
68. a) F. E. Kühn, A. M. Santos, M. Abrantes, Chem. Rev. 2006, 106, 2455;
69. b) C. Freund, M. Abrantes, F. E. Kühn, J. Organomet. Chem. 2006, 691, 3718.
70. a) D. R. Lal, S. Keka. Indian J. Chem. Sect. A 2000, 39, 1177-1181;
71. b) S. Shekhar, K. Abul, J. Indian Chem. Soc. 2002, 79, 502-504;
72. c) P. P. Singh, B. Srivastava, Indian J. Chem. Sect. A 1986, 25, 1109-1113.
73. a) G. M. Sheldrick. SHELXTL97. University of Göttingen. Germany. 1997;
74. b) SMART V5.618 Software for the CCD Detector System. Bruker Analytical X-ray Systems, Inc., Madison, WI, 1998:
75. c) SAINTPLUS, V6.45, A Software for the CCD Detector System. Bruker Analytical X-ray System. Inc., Madison. WI, 1998:
76. d) SADABS V2.10. Program for absorption correction using SMART CCD data based on the method of Blessing: R. H. Blessing. Acta Crystallogr. Sect. A 1995, A51, 33.