Design and performance of rigid nanosize multimetallic cartwheel pincer compounds as Lewis-acid catalysts

Organometallics

Volumn 20, Issue 14, 2001, Pages 3159-3168

  Dijkstra, Harm P ^a   Meijer, Michel D ^a   Patel, Jim ^b   Kreiter, Rob ^a   Van Klink, Gerard P M ^a   Lutz, Martin ^c   Spek, Anthony L ^c   Canty, Allan J ^b   Van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UNIVERSITY OF TASMANIA   (Australia)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID CATALYSTS; RIGID CARTWHEEL PINCER METAL COMPLEXES;

CATALYST ACTIVITY; CATALYSTS; COMPLEXATION; CONDENSATION REACTIONS; CRYSTAL STRUCTURE; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

EID: 0035833305     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0101689     Document Type: Article

References (56)

1. For a review on the application of metallodendrimers as homogeneous catalysts, see: Kreiter, R.; Kleij, A. W.; Klein Gebbink, R. J. M.; van Koten, G. Topics in Current Chemistry, Dendrimers IV by Prof. Dr. F. Vögtle.
2. (a) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
3. (b) Kragl, U.; Dreisbach, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 642.
4. (c) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. 1997, 36, 1526.
5. (d) Giffels, G.; Beliczey, J.; Felder, M.; Kragl, U. Tetrahedron: Asymmetry 1998, 9, 691.
6. (e) Brinkmann, N.; Giebel, D.; Lohmer, G.; Reetz, M. T.; Kragl, U. J. Catal. 1999, 183, 163.
7. (f) Hovestad, N. J.; Eggeling, E. B.; Heidbüchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. 1999, 38, 1655.
8. (g) De Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Commun. 1999, 1623.
9. (h) Dijkstra, H. P.; Steenwinkel, P.; Grove, D. M.; Lutz, M.; Spek, A. L.; van Koten, G. Angew. Chem., Int. Ed. 1999, 38, 2186.
10. (i) Albrecht, M.; Hovestad, N. J.; Boersma, J.; van Koten, G. Chem. Eur. J. 2001, 7, 1289.
11. (j) Kleij, A. W.; Gossage, R. A.; Klein Gebbink, R. J. M.; Brinkman, N.; Reijerse, E. J.; Kragl, U.; Lutz, M.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 2000, 122, 12112.
12. (a) Mahrwald, R. Chem. Rev. 1999, 99, 1095 and references therein.
13. (b) Christoffers, J. Eur. J. Org. Chem. 1998, 1259 and references therein.
14. (c) Drury, W. J.; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006.
15. Diels-Aldr Reactions: (a) Bruin, M. E.; Kündig, E. P. Chem. Commun. 1998, 2635.
16. (b) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-I.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. J. Am. Chem. Soc. 1998, 120, 3074.
17. (c) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403.
18. (d) Davies, D. L.; Fawcett, J.; Garrat, S. A.; Russell, D. R. Chem. Commun. 1997, 1351.
19. (e) Evans, D. A.; Murray, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
20. (f) Kündig, E. P.; Bourdin, B.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1856.
21. (g) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
22. Aldol reactions: (a) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032.
23. (b) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859.
24. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319.
25. (d) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814.
26. (e) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077.
27. Michael reactions: (a) Blacker, A. J.; Clarke, M. L.; Loft, M. S.; Mahon, M. F.; Williams, J. M. J. Organometallics 1999, 18, 2867.
28. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439.
29. (c) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Wade Downey, C.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134.
30. Alkylation reactions: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
31. (b) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723.
32. (a) Gorla, F.; Togni, A.; Venanzi, L. M.; Albinati, A.; Lianza, F. Organometallics 1994, 13, 1607.
33. (b) Longmire, J. M.; Zhang, X.; Shang, M. Organometallics 1998, 17, 4374.
34. (a) Stark, M. A.; Richards, C. J. Tetrahedron Lett. 1997, 38, 5881.
35. (b) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282.
36. Motoyama, Y.; Narusawa, H.; Nishiyama, H. Chem. Commun. 1999, 131.
37. For the synthesis of 3a see: Alsters, P. L.; Baesjou, P. J.; Janssen, M. D.; Kooijman, H.; Sicherer-Roetman, A.; Spek, A. L.; van Koten, G. Organometallics 1992, 11, 4124.
38. For the synthesis of 1b and 3b see: Canty, A. J.; Honeyman, R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1990, 389, 277.
39. For the synthesis of 1a from 3a see: Grove, D. M.; van Koten, G.; Louwen, J. N.; Noltes, J. G.; Spek, A. L.; Ubbels, H. J. C. J. Am. Chem. Soc. 1984, 104, 6609.
40. Hartshorn, C. M.; Steel, P. J. Organometallics 1998, 17, 3487.
41. (a) For the synthesis of 3d see: Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1983, 259, C6.
42. (b) For the synthesis of 3e see: Lucena, N.; Casabo, J.; Escriche, L.; Sanchez-Castello, G.; Teixidor, F.; Kivekäs, R.; Sillanpää, R. Polyhedron 1996, 15, 3009.
43. Duchêne, K.-H.; Vögtle, F. Synthesis 1986, 659.
44. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
45. Procedure reported by: (a) Loeb, S. J.; Shimizu, G. K. H. J. Chem. Soc., Chem. Commun. 1993, 1396.
46. (b) Kickham, J. E.; Loeb, S. J. Inorg. Chem. 1994, 33, 4351.
47. Van de Kuil, L. A.; Luitjes, H.; Grove, D. M.; Zwikker, J. W.; van der Linden, J. G. M.; Roelofsen, A. M.; Jenneskens, L. W.; Drenth, W.; van Koten, G. Organometallics 1994, 13, 471.
48. Modification of a reported method wsa used: Elmorsy, S. S.; Pelter, A.; Smith, K. Tetrahedron Lett. 1991, 32, 4175.
49. Canty, A. J.; Patel, J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 2000, 599, 195.
50. Canty, A. J.; Lee, C. V. Organometallics 1982, 1, 1063.
51. Dijkstra, H. P.; Kruithof, K.; Ronde, N.; Vogt, D.; van Klink, G. P. M.; van Koten, G. To be submitted for publication. SelRo nanofiltration membranes (MPF-60) were purchased from Koch Membrane Systems Inc., Düsseldorf, Germany; further product information may be found at http://www.kochmembrane.com.
52. Drew, D.; Doyle, J. R.; Shaver, A. G. Inorg. Synth. 1972, 13, 47.
53. Derived values do not contain the contribution of the disordered solvent.
54. Spek, A. L. PLATON: A Multipurpose Crystallographic Tool; Utrecht University, The Netherlands, 2000.
55. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF97 Program System, Technical Report of the Crystallography Laboratory; University of Nijmegen, Nijmegen, The Netherlands, 1997.
56. Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Refinement; University of Göttingen, Göttingen, Germany, 1997.