Cationic rare-earth metal trimethylsilylmethyl complexes supported by THF and 12-crown-4 ligands: Synthesis and structural characterization

Inorganic Chemistry

Volumn 44, Issue 19, 2005, Pages 6777-6788

  Elvidge, Benjamin R ^a   Arndt, Stefan ^a   Zeimentz, Peter M ^a   Spaniol, Thomas P ^a   Okuda, Jun ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 25144489037     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0511165     Document Type: Article

References (95)

1. Cationic rare-earth metal complexes incorporating only π-bound hydrocarbyl ligands utilize three ligand types: "Cp": (a) Evans, W. J.; Bloom, I.; Grate, J. W.; Hughes, L. A.; Hunter, W. E.; Atwood, J. L. Inorg. Chem. 1985, 24, 4620.
2. (b) Hazin, P. N.; Bruno, J. W.; Schulte, G. K. Organometallics 1990, 9, 416.
3. (c) Evans, W. J.; Ulibarri, T. A.; Chamberlain, L. R.; Ziller, J. W.; Alvarez, D., Jr. Organometallics 1990, 9, 2124.
4. (d) Heeres, H. J.; Meetsma, A.; Teuben, J. H. J. Organomet. Chem. 1991, 414, 351.
5. (e) Evans, W. J.; Kociok-Köhn, G.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1081.
6. (f) Deng, D.; Zheng, X.; Qian, C.; Sun, J.; Dormond, A.; Baudry, D.; Visseaux, M. J. Chem. Soc., Dalton Trans. 1994, 1665.
7. (g) Schumann, H.; Winterfeld, J.; Keitsch, M. R.; Herrmann, K.; Demtschuk, J. Z. Anorg. Allg. Chem. 1996, 622, 1457.
8. (h) Yuan, F.; Shen, Q.; Sun, J. J. Organomet. Chem. 1997, 538, 241.
9. (i) Song, X.; Thornton-Pett, M.; Bochmann, M. Organometallics 1998, 17, 1004.
10. (j) Evans, W. J.; Seibel, C. A.; Ziller, J. W. J. Am. Chem. Soc. 1998, 120, 6745.
11. (k) Evans, W. J.; Seibel, C. A.; Forrestal, K. J.; Ziller, J. W. J. Coord. Chem. 1999, 48, 403.
12. (l) Xie, Z.; Liu, Z.; Chui, K.; Xue, F.; Mak, T. C. W. J. Organomet. Chem. 1999, 588, 78.
13. (m) Molander, G. A.; Rzasa, R. M. J. Org. Chem. 2000, 65, 1215.
14. (n) Evans, W. J.; Davis, B. L.; Ziller, J. W. Inorg. Chem. 2001, 40, 6341.
15. (o) Kaita, S.; Hou, Z. M.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiuchi, A. C.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 179.
16. (p) Evans, W. J.; Perotti, J. M.; Brady, J. C.; Ziller, J. W. J. Am. Chem. Soc. 2003, 125, 5204.
17. (q) Evans, W. J.; Perotti, J. M.; Ziller, J. W. J. Am. Chem. Soc. 2005, 127, 3894.
18. 8": (r) Cendrowski-Guillaume, S. M.; Nierlich, M.; Lance, M.; Ephritikhine, M. Organometallics 1998, 17, 786.
19. (s) Cendrowski-Guillaume, S. M.; Le Gland, G.; Nierlich, M.; Ephritikhine, M. Organometallics 2000, 19, 5654.
20. (t) Cendrowski-Guillaume, S. M.; Nierlich, M.; Ephritikhine, M. Eur. J. Inorg. Chem. 2001, 1495.
21. "allyl": (u) Taube, R.; Maiwald, S.; Sieler, J. J. Organomet. Chem 2001, 621, 327.
22. (v) Kaita, S.; Hou, Z.; Wakatsuki, Y. US2002/0119889A1.
23. Cationic rare-earth metal complexes incorporating one σ-bound alkyl and another different monoanionic ligand utilize four ligand types: "LX": (a) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522.
24. (b) Bambirra, S.; Bouwkamp, M. W.; Meetsma, A.; Hessen, B. J. Am. Chem. Soc. 2004, 126, 9182.
25. 2X": (c) Schaverien, C. J. Organometallics 1992, 11, 3476.
26. (d) Lee, L. W. M.; Piers, W. E.; Elsegood, M. R. J.; Clegg, W.; Parvez, M. Organometallics 1999, 18, 2947.
27. (e) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132.
28. (f) Hayes, P. G.; Piers, W. E.; Parvez, M. J. Am. Chem. Soc. 2003, 125, 5622.
29. (g) Hayes, P. G.; Welch, G. C.; Emslie, D. J. H.; Noack, C. L.; Piers, W. E.; Parvez, M. Organometallics 2003, 22, 1577.
30. (h) Cameron, T. M.; Gordon, J. C.; Michalczyk, R.; Scott, B. L. Chem. Commun. 2003, 2282.
31. (i) Henderson, L. D.; MacInnis, G. D.; Piers, W. E.; Parvez, M. Can. J. Chem. 2004, 82, 162.
32. (j) Luo, Y.; Baldamus, J.; Hou, Z. J. Am. Chem. Soc. 2004, 126, 13910.
33. 3X": (k) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637.
34. (l) Tazelaar, C. G. J.; Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Organometallics 2004, 23, 936.
35. (m) Bambirra, S.; Boot, S. J.; van Leusen, D.; Meetsma, A.; Hessen, B. Organometallics 2004, 23, 1891.
36. (n) Hessen, B.; Bambirra, S., WO2002032909.
37. (o) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Schaffer, T. D., WO0018808.
38. 5X": (p) Lee, L.; Berg, D. J.; Einstein, F. W.; Batchelor, R. J. Organometallics 1997, 16, 1819.
39. 3": (a) Arndt, S.; Spaniol, T. P.; Okuda, J. Chem. Commun. 2002, 896.
40. (b) Arndt, S.; Zeimentz, P. M.; Spaniol, T. P.; Okuda, J.; Honda, M.; Tatsumi, K. Dalton Trans. 2003, 3622.
41. (c) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075.
42. (d) Okuda, J.; Arndt, S.; Matsui, S., JP2005015579.
43. (e) Ward, B. D., Bellemin-Laponnaz, S.; Gade, L. H. Angew. Chem., Int. Ed. 2005, 44, 1668.
44. (f) Lawrence, S. C.; Ward, B. D.; Dubberley, S. R.; Kozak, C. M.; Mountford, P. Chem. Commun. 2003, 2880.
45. 3": (g) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45.
46. Lauterwasser, F.; Hayes, P. G.; Bräse, S.; Piers, W. E.; Schafer, L. L. Organometallics 2004, 23, 2234.
47. Taube, R. In Metalorganic Catalysts for Synthesis and Polymerisation; Kaminsky, W., Ed.; Springer: Berlin, Germany, 1999; p 531.
48. Arndt, S.; Okuda, J. Adv. Synth. Catal. 2005, 347, 339.
49. Pyridine activation processes involving rare-earth metal alkyl and hydride complexes are known, see Kirillov, E.; Lehmann, C. W.; Razavi, A.; Carpentier, J.-F. Eur. J. Inorg. Chem. 2004, 943 and references therein.
50. 5) with clean 12-crown-4 incorporation.
51. 9) requires 11.24%.
52. 2, 15a and an alkyl-free byproduct.
53. 1H} NMR spectra are similar to those of the co-product observed at low concentration in the formation of 15a. Alkyl-free tricationic rare-earth metal borate complexes are known: (a) Sauro, L. J.; Moeller, T. J. Inorg. Nucl. Chem. 1968, 30, 953.
54. (b) Thomas, R. R.; Chebolu, V.; Sen, A. J. Am. Chem. Soc. 1986, 108, 4096.
55. 8 required 10 days for complete loss of monocation resonances. The Lu analysis of the worked-up product was 2-3% too high in Lu for the dication.
56. 2 after 2 days at room temperature.
57. (a) Estler, F.; Eickerling, G.; Herdtweck, E.; Anwander, R. Organometallics 2003, 22, 1212.
58. (b) Lara-Sanchez, A.; Rodriguez, A.; Hughes, D. L.; Schormann, M.; Bochmann, M. J. Organomet. Chem. 2002, 663, 63.
59. (c) Ward, B. D.; Dubberley, S. R.; Maisse-Francois, A.; Gade, L. H.; Mountford, P. J. Chem. Soc., Dalton Trans. 2002, 4649.
60. (d) Emslie, D. J. H.; Piers, W. E.; Parvez, M.; McDonald, R. Organometallics 2002, 21, 4226 and references therein,
61. (e) Hayes, P. G.; Piers, W. E.; Lee, L. W. M.; Knight, L. K.; Parvez, M.; Elsegood, M. R. J.; Clegg, W. Organometallics 2001, 20, 2533.
62. (a) Willey, G. R.; Meehan, P. R.; Drew, M. G. B. Polyhedron 1996, 15, 1397.
63. (b) Nishihara, S.; Takamatsu, N.; Akutagawa, T.; Hasegawa, T.; Nakamura, T. Synth. Met. 2001, 121, 1806.
64. (a) Willey, G. R.; Lakin, M. T.; Alcock, N. W. J. Chem. Soc., Chem. Commun. 1992, 1619.
65. (b) Willey, G. R.; Lakin, M. T.; Alcock, N. W. J. Chem. Soc., Dalton Trans. 1993, 3407.
66. Brown, M. D.; Levason, W.; Murray, D. C.; Popham, M. C.; Reid, G.; Webster, M. Dalton Trans. 2003, 857.
67. (a) Westerhausen, M.; Hartmann, M.; Schwarz, W. Inorg. Chim. Acta 1998, 269, 91.
68. (b) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kojicprodic, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726.
69. (c) den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Smeets, W. J. J.; Spek, A. L. J. Organomet. Chem. 1987, 327, 31.
70. (d) Coughlin, E. B.; Henling, L. M.; Bercaw, J. E. Inorg. Chim. Acta 1996, 242, 205.
71. (e) Arndt, S.; Beckerle, K.; Zeimentz, P. M.; Spaniol, T. P.; Okuda, J. Unpublished work.
72. Rogers, R. D.; Rollins, A. N.; Benning, M. M. Inorg. Chem. 1988, 27, 3826.
73. (a) Evans, W. J.; Olofson, J. M.; Ziller, J. W. J. Am. Chem. Soc. 1990, 112, 2308.
74. (b) Sobota, P.; Utko, J.; Szafert, S. Inorg. Chem. 1994, 33, 5203.
75. (c) Chiu, K. Y.; Zhang, Z. Y.; Mak, T. C. W.; Xie, Z. W. J. Organomet. Chem. 2000, 614, 107.
76. Higher order downfield multiplets for crown ether ligands have been observed in similar compounds and arise from the diastereotopic methylene protons of the exocyclic crown ether when the coordination is rigid on the NMR time scale (see ref 3a,b). The apparent discrepancy with the solid-state structure can be explained by a carousel-like 12-crown-4 oxygen rotation that is fast on the NMR time scale. A very low intensity signal at 3.62 ppm, slightly broad at 25°C and sharp at -10°C, was assigned to a trace free 12-crown-4 impurity.
77. Thomson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.M Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203.
78. Deelman, B.-J.; Stevels, W. M.; Teuben, J. H.; Lakin, M. T.; Spek, A. L. Organometallics 1994, 13, 3881.
79. Watson, P. L. J. Chem. Soc., Chem. Commun. 1983, 276.
80. Evans, W. J.; Meadows, J. H.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1984, 106, 1291.
81. YC = 33.2 Hz) for the pyridine α-carbon (see ref 23).
82. 2Ph): Horton, A. D.; de With, J.; van der Linden, A. J.; van de Weg, H. Organometallics 1996, 15, 2672.
83. 4 coordination has also been noted in cationic zirconium complexes: (a) Bochmann, M.; Karger, G.; Jaggar, A. J. J. Chem. Soc., Chem. Commun. 1990, 1038.
84. (b) Horton, A. D.; Frijns, J. H. G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1152.
85. (a) Lappert, M. F.; Pearce, R. J. Chem. Soc., Chem. Commun. 1973, 126.
86. (b) Evans, W. J.; Brady, J. C.; Ziller, J. W. J. Am. Chem. Soc. 2001, 123, 7711.
87. (c) Schumann, H.; Freckmann, D. M. M.; Dechert, S. Z. Anorg. Allorg. Chem., 2002, 628, 2422.
88. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
89. Siemens. ASTRO, SAINT and SADABS. Data Collection and Processing Software for the SMART System; Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1996.
90. Sheldrick, G. M. SHELXS-86, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1986.
91. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
92. International Tables for X-ray Crystallography, Vol. C; Kluwer Academic Publishers: Dordrecht, 1992.
93. (a) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045.
94. (b) Bambirra, S.; Brandsma, M. J. R.; Brussee, E. A. C.; Meetsma, A.; Hessen, B.; Teuben, J. H.; Organometallics 2000, 19, 3197.
95. Arndt, S.; Spaniol, T. P.; Okuda, J. Organometallics 2003, 22, 775 and references therein.