Triazenide complexes of the heavier alkaline earths: Synthesis, characterization, and suitability for hydroamination catalysis

Inorganic Chemistry

Volumn 47, Issue 16, 2008, Pages 7366-7376

  Barrett, Anthony G M ^a   Crimmin, Mark R ^a   Hill, Michael S ^b   Hitchcock, Peter B ^c   Kociok Köhn, Gabriele ^c   Procopiou, Panayiotis A ^d  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b University of Bath Claverton Down   (United Kingdom)

^c UNIVERSITY OF SUSSEX   (United Kingdom)

^d GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE EARTH METAL; LIGAND; ORGANOMETALLIC COMPOUND; TRIAZINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS; TEMPERATURE;

AMINATION; CATALYSIS; LIGANDS; METALS, ALKALINE EARTH; ORGANOMETALLIC COMPOUNDS; TEMPERATURE; TRIAZINES;

EID: 50449094022     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic800789x     Document Type: Article

References (84)

1. (a) Crimmin, M. R.; Casely, I. J.; Hill, M. S. J. Am. Chem. Soc. 2005, 127, 2042.
2. (b) Crimmin, M. R.; Barrett, A. G. M.; Hill, M. S.; Hitchcock, P. B.; Procopiou, P. A. Organometallics 2007, 26, 2953.
3. (c) Crimmin, M. R.; Barrett, A. G. M.; Hill, M. S.; Hitchcock, P. B.; Procopiou, P. A. Organometallics 2008, 27, 497.
4. (d) Barrett, A. G. M.; Crimmin, M. R.; Hill, M. S.; Kociok-Köhn, G.; Lachs, J. R.; Mahon, M. F.; Procopiou, P. A.,submitted for publication.
5. (e) Crimmin, M. R.; Barrett, A. G. M.; Casely, I. J.; HillM. S.; Kociok-Köhn, G.; Procopiou, P. A.,in preparation.
6. (a) Datta, S.; Roesky, P. W.; Blechert, S. Organometallics 2007, 26, 4392.
7. (b) Datta, S.; Gamer, M. T.; Roesky, P. W. Organometallics 2008, 27, 1207.
8. (a) Buch, F.; Brettar, J.; Harder, S. Angew. Chem., Int. Ed. 2006, 45, 2741.
9. (b) Spielmann, J.; Harder, S. Eur. J. Inorg. Chem. 2008, 1480.
10. (a) Weeber, A.; Harder, S.; Brintzinger, H. H. Organometallics 2000, 19, 1325.
11. (b) Harder, S.; Feil, F.; Knoll, K. Angew. Chem., Int. Ed. 2001, 40, 4261.
12. (c) Harder, S.; Feil, F.; Weeber, A. Organometallics 2001, 20, 1044.
13. (d) Harder, S.; Feil, F. Organometallics 2002, 21, 2268.
14. (e) Feil, F.; Harder, S. Eur. J. Inorg. Chem. 2003, 3401.
15. (f) Piesik, D. f. J.; Häbe, K.; Harder, S. Eur. J. Inorg. Chem. 2007, 5652.
16. (a) Zhong, Z.; Schneiderbauer, S.; Dijkstra, P. J.; Westerhausen, M.; Feijen, J. J. Polym. Environ. 2002, 9, 31.
17. (b) Zhong, Z.; Schneiderbauer, S.; Dijkstra, P. J.; Westerhausen, M.; Feijen, J. Polym. Bull. 2003, 51, 175.
18. (c) Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Chem. Commun. 2003, 48.
19. (d) L Piao, L.; Deng, M.; Chen, X.; Jiang, L.; Jing, X. Polymer 2003, 44, 2331.
20. (e) Westerhausen, M.; Schneiderbauer, S.; Kneifel, A. N.; Sohl, Y.; Mayer, P.; Nöth, H.; Zhong, Z.; Dijkstra, P. J.; Feijen, J. Eur. J. Inorg. Chem. 2003, 3432.
21. (f) Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Inorg. Chem. 2004, 43, 6717.
22. (g) Chisholm, M. H.; Gallucci, J. C.; Yaman, G. Chem. Commun. 2006, 1872.
23. (h) Sarazin, Y.; Howard, R. H.; Hughes, D. L.; Humphrey, S. M.; Bochmann, M. Dalton Trans. 2006, 340.
24. (i) Davidson, M. G.; O'Hara, C. T.; Jones, M. D.; Keir, C. G.; Mahon, M. F.; Kociok-Köhn, G. Inorg. Chem. 2007, 46, 7686.
25. Orzechowski, L.; Harder, S. Organometallics 2007, 26, 2144.
26. Crimmin, M. R.; Barrett, A. G. M.; Hill, M. S.; Procopiou, P. A. Org. Lett. 2007, 9, 331.
27. Avent, A. G.; Crimmin, M. R.; Hill, M. S.; Hitchcock, P. B. Dalton Trans. 2005, 278.
28. (a) Barker, J.; Kilner, M. Coord. Chem. Rev. 1994, 133, 219.
29. (b) Cotton, F. A.; Lin, C.; Murillo, C. A. PNAS 2002, 99, 4810.
30. (a) Meldola, R.; Streatfeild, F. W. J. Chem. Soc., Trans. 1887, 51, 434.
31. (b) Dwyer, F. P. J. Am. Chem. Soc. 1941, 63, 78.
32. (c) Harris, C. M.; Hoskins, B. F.; Martin, R. L. J. Chem. Soc. 1959, 3728.
33. For s-block triazenide complexes see,(a) Gantzel, P.; Walsh, P. J. Inorg. Chem. 1998, 37, 3450.
34. (b) Westhusin, S.; Gantzel, P.; Walsh, P. J. Inorg. Chem. 1998, 37, 5956.
35. (c) Nimitsiriwat, N.; Gibson, V. C.; Marshall, E. L.; Takolpuckdee, P.; Tomov, A. K.; White, A. J. P.; Williams, D. J.; Elsegood, M. R. J.; Dale, S. H. Inorg. Chem. 2007, 46, 9988.
36. (d) Hauber, S-.O.; Lissner, F.; Deacon, G. B.; Niemeyer, M. Angew. Chem., Int. Ed. 2005, 44, 5871.
37. (e) Lee, H. S.; Hauber, S.-O.; Vinduš, D.; Niemeyer, M. Inorg. Chem. [Online early access]. DOI: 10.1021/ic800029z. Published Online: 2008.
38. (f) Lee, H. S.; Niemeyer, M. Inorg. Chem. 2006, 45, 6126.
39. (g) Brinckman, F. E.; Haiss, H. S.; Robb, R. A. Inorg. Chem. 1965, 4, 936.
40. For late TM triazenide complexes see,(a) Nuricumbo-Escobar, J. J.; Campos-Alvarado, C.; Rios-Moreno, G.; Morales-Morales, D.; Walsh, P. J.; Parra-Hake, M. Inorg. Chem. 2007, 46, 6182.
41. (b) Rios-Moreno, G.; Aguirre, G.; Parra-Hake, M.; Walsh, P. J. Polyhedron 2003, 22, 563.
42. (c) Albertin, G.; Antoniutti, S.; Bedlin, M.; Castro, J.; Garcia-Fontan, S. Inorg. Chem. 2006, 45, 3816.
43. (d) Adams, C. J.; Baber, R. A.; Connelly, N. G.; Harding, P.; Hayward, O. D.; Kandiah, M.; Orpen, A. G. Dalton Trans. 2006, 1749.
44. (e) Connelly, N. G.; Hayward, O. D.; Klangsinsirikul, P.; Orpen, A. G.; Rieger, P. H. Chem. Commun. 2000, 963.
45. (f) Hörner, M.; Manzoni de Oliveira, G.; Koehler, E. G.; CantoVisentin, L. D. J. Organomet. Chem. 2006, 691, 1311.
46. (g) Hörner, M.; Casagrande, I. C.; Fenner, H.; Daniels, J.; Beck, J. Acta Crystallogr. 2003, C59, 424.
47. (h) Peregudov, A. S.; Kravtsov, D. N.; Drogunova, G. I.; Starikova, Z. A.; Yanovsky, A. I. J. Organomet. Chem. 2000, 597, 164.
48. For group 13 triazenide complexes see. (a) Leman, J. T.; Braddock-Wilking, J.; Coolond, A. J.; Barron, A. R. Inorg. Chem. 1993, 32, 4324.
49. (b) Leman, J. T.; Barron, A. R.; Ziller, J. W.; Kren, R. M. Polyhedron 1989, 8, 1909, and refs 11e and 11g.
50. (a) Junk, P. C.; Cole, M. L. Chem. Commun. 2007, 1579.
51. (b) Cole, M. L.; Junk, P. C. J. Organomet. Chem. 2003, 666, 55.
52. (c) Cole, M. L.; Davies, A. J.; Jones, C.; Junk, P. C. New J. Chem. 2005, 29, 1404.
53. Jones, C.; Junk, P. C.; Platts, J. A.; Rathmann, D.; Stasch, A. Dalton Trans. 2005, 2497.
54. (a) Cole, M. L.; Junk, P. C. New J. Chem. 2005, 29, 135.
55. (b) Cole, M. L.; Deacon, G. B.; Forsyth, C. M.; Konstas, K.; Junk, P. C. Dalton Trans. 2006, 3360.
56. (a) King, R. B.; Nainan, K. C. Inorg. Chem. 1975, 14, 272.
57. (b) Inglis, T.; Kilner, M. J. Chem. Soc., Dalton Trans. 1975, 930.
58. (a) Lyakhov, A. S.; Gaponik, P. N.; Pytleva, D. S.; Voitekhovich, S. V.; Ivashkevich, L. S. Acta Crystallogr. 2004, C60, 421.
59. (b) Hanot, V. P.; Robert, T. D.; Hassnoot, J. G.; Kooijman, H.; Spek, A. L. J. Chem. Crystallogr. 1999, 29, 299.
60. (c) Hanot, V. P.; Robert, T. D.; Kolnaar, J. J. A.; Haasnoot, J. G.; Kooijman, H.; Spek, A. L. Inorg. Chim. Acta 1997, 256, 327.
61. (a) Hartman, W. W.; Dickey, J. B. Org. Synth. 1943, 162, Coll. Vol. 2.
62. (b) Hill, D. T.; Stanley, K. G.; Williams, J. E. K.; Loev, B.; Fowler, P. J.; McCafferty, J. P.; Macko, E.; Berkoff, C. E.; Ladd, C. B. J. Med. Chem. 1983, 26, 865.
63. Chen, N.; Barra, M.; Lee, I.; Chahal, N. J. Org. Chem. 2002, 67, 2271.
64. (a) Forber, C. L.; Kelusky, E. C.; Bunce, N. J. J. Am. Chem. Soc. 1985, 107, 5884.
65. (b) Bunce, N. J.; Ferguson, G.; Forber, C. L.; Stachnyk, G. J. J. Org. Chem. 1987, 52, 394.
66. (a) McCormick, M. J.; Sockwell, S. C.; Davis, C. E. H.; Hanusa, T. P.; Huffman, J. C. Organometallics 1989, 8, 2044.
67. (b) Harvery, M. J., Jr.; Hanusa, T. P.; Young, V. G. J. Organomet. Chem. 2001, 626, 43.
68. (c) Harvery, M. J.; Hanusa, T. P. Organometallics 2000, 19, 1556.
69. (d) Burkey, D. J.; Alexander, E. K.; Hanusa, T. P. Organometallics 1994, 13, 2773.
70. (f) El-Kaderi, H. M.; Heeg, M. J.; Winter, C. H. Polyhedron 2006, 25, 224.
71. (g) Datta, S.; Gamer, M. T.; Roesky, P. W. Dalton Trans. [Online early access] DOI: 10.1039/b719552d. Published Online: 2008.
72. Vaartstra, B. A.; Huffman, J. C.; Streib, W. E.; Caulton, K. G. Inorg. Chem. 1991, 30, 121.
73. M. J. Frisch et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
74. Minima were confirmed by independent frequency calculations.
75. (a) Avent, A. G.; Crimmin, M. R.; Hill, M. S.; Hitchcock, P. B. Dalton Trans. 2004, 3166.
76. (b) Barrett, A. G. M.; Crimmin, M. R.; Hill, M. S.; Kociok-Köhn, G.; Lachs, J. R.; Procopiou, P. A. Dalton Trans. 2008, 1292.
77. (c) Barrett, A. G. M.; CrimminM. R.; Hill, M. S.; Mahon, M. F.; Procopiou, P. A.;in preparation.
78. (a) Boncella, J. M.; Coston, C. J.; Cammack, J. K. Polyhedron 1991, 10, 769.
79. (b) Tanner, P. S.; Burkey, D. J.; Hanusa, T. P. Polyhedron 1995, 14, 331.
80. (a) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
81. (b) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
82. Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2003, 125, 12584.
83. Otwinowski, Z.; Minor, W. DENZO-SCALEPACK, Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology, Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press.: New York, 1997; Volume 276, Macromolecular Crystallography, part A, pp 307-326.
84. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.