Formation of zirconocenes containing vinyl-imine and keteniminate species from zirconacycles and diphenylacetonitrile

Organometallics

Volumn 30, Issue 13, 2011, Pages 3464-3467

  Zhao, Jing ^a   Zhang, Shaoguang ^b   Zhang, Wen Xiong ^b   Xi, Zhenfeng ^b,c  

^a INSTITUTE OF CHEMISTRY   (China)

^b PEKING UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BONDS; EFFECT OF PH; INTRAMOLECULAR PROTON TRANSFER; ZIRCONOCENE COMPLEXES; ZIRCONOCENES;

ZIRCONIUM COMPOUNDS;

NITROGEN COMPOUNDS;

EID: 79960027320     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200404p     Document Type: Article

References (79)

1. For reviews of zirconacycles, see: Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701
2. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769
3. Takahashi, T.; Xi, Z.; Kotora, M. Rec. Res. Dev. Pure Appl. Chem. 1998, 2, 515-525
4. Takahashi, T.; Kotora, M.; Hara, R.; Xi, Z. Bull. Chem. Soc. Jpn. 1999, 72, 2591-2602
5. Takahashi, T.; Li, Y. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinhein, Germany, 2002; pp 50-85.
6. Erker, G.; Kehr, G.; Fröhlich, R. J. Organomet. Chem. 2004, 689, 4305-4318
7. Negishi, E. Dalton Trans. 2005, 827-848
8. Rosenthal, U.; Burlakov, V. V.; Bach, M. A.; Beweries, T. Chem. Soc. Rev. 2007, 36, 719-728
9. Suzuki, N.; Hashizume, D. Coord. Chem. Rev. 2010, 254, 1307-1326
10. Chen, C.; Xi, C. Chin. Sci. Bull. 2010, 55, 3235-3247
11. Selected examples of zirconacyclopentenes: Takahashi, T.; Xi, Z.; Kotora, M.; Xi, C.; Nakajima, K. Tetrahedron Lett. 1996, 37, 7521-7524
12. Liu, Y.; Sun, W.-H.; Nakajima, K.; Takahashi, T. Chem. Commum. 1998, 1133-1134
13. Dumond, Y.; Negishi, E. J. Am. Chem. Soc. 1999, 121, 11223-11224
14. Zhao, C.; Lu, J.; Yan, J.; Xi, Z. Tetrahedron Lett. 2003, 44, 6895-6898
15. Norton, D.; Whitby, R. J.; Griffen, E. Chem. Commun. 2004, 1214-1215
16. Liu, Y.; Gao, H. Org. Lett. 2006, 8, 309-311
17. Chen, J.; Li, Y.; Gao, H.; Liu, Y. Organometallics 2008, 27, 5619-5623
18. Chen, C.; Liu, Y.; Xi, C. Tetrahedron Lett. 2009, 50, 5434-5436
19. Zhou, Y.; Chen, J.; Zhao, C.; Wang, E.; Liu, Y.; Li, Y. J. Org. Chem. 2009, 74, 5326-5330
20. Zheng, W.; Wu, Y.; Zheng, F.; Hu, L.; Hong, Y. Tetrahedron Lett. 2010, 51, 4702-4704
21. Selected examples of zirconacyclopentadienes: Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829-2832
22. Erker, G.; Zwettler, R.; Krüger, C.; Hyla-Kryspin, I.; Gleiter Organometallics 1990, 9, 524-530
23. Ruwwe, J.; Erker, G.; Fröhlich, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 80-82
24. Mahieu, A.; Miquel, Y.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Organometallics 1997, 16, 3086-3088
25. Takahashi, T.; Sun, W.-H.; Xi, C.; Kotora, M. Chem. Commun. 1997, 2069-2070
26. Nakamoto, M.; Tilley, T. D. Organometallics 2001, 20, 5515-5517
27. Xi, Z.; Fan, H.-T.; Mito, S.; Takahashi, T. J. Organomet. Chem. 2003, 682, 108-112
28. Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A.; Rosenthal, U. Organometallics 2004, 23, 4160-4165
29. Chen, C.; Xi, C.; Jiang, Y.; Hong, X. J. Am. Chem. Soc. 2005, 127, 8024-8025
30. Liu, Y.; Liu, M.; Song, Z. J. Am. Chem. Soc. 2005, 127, 3662-3663
31. Yan, X.; Zhou, Y.; Xi, C. Chem. Commun. 2010, 46, 7801-7803
32. Gessner, V. H.; Tannacl, J. F.; Miller, A. D.; Tilley, T. D. Acc. Chem. Res. doi: 10.1021/ar100148g.
33. Selected examples of azazirconacycles: Negishi, E.; Holms, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336-3346
34. Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690
35. Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705-3723
36. Binger, P.; Sandmeyer, F.; Krüger, C. Organometallics 1995, 14, 2969-2976
37. Zippel, T.; Arndt, P.; Ohff, A.; Spannenberg, A.; Kempe, R.; Rosenthal, U. Organometallics 1998, 17, 4429-4437
38. Takahashi, T.; Xi, C.; Xi, Z.; Kageyama, M.; Fischer, R.; Nakajima, K.; Negishi, E. J. Org. Chem. 1998, 63, 6802-6806
39. Cadierno, V.; Zablocka, M.; Donnadieu, B.; Igau, A.; Majoral, J.-P. Angew. Chem., Int. Ed. 2000, 39, 4524-4528
40. Takahashi, T.; Liu, Y.; Xi, C.; Huo, S. Chem. Commun. 2001, 31-32
41. Takahashi, T.; Tsai, F.-Y.; Li, Y.; Wang, H.; Kondo, Y.; Yamanaka, M.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 5059-5067
42. Liu, Y.; Shen, B.; Kotora, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2002, 67, 7019-7028
43. Ruck, R. T.; Zuckerman, R. L.; Krska, S. W.; Bergman, R. G. Angew. Chem., Int. Ed. 2004, 43, 5372-5374
44. Liu, Y.; Yan, B. Organometallics 2006, 25, 544-547
45. Bach, M. A.; Beweries, T.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A.; Rosenthal, U. Organometallics 2007, 26, 4592-4597
46. Fu, X.; Chen, J.; Li, G.; Liu, Y. Angew. Chem., Int. Ed. 2009, 48, 5500-5504
47. Kaleta, K.; Ruhmann, M.; Theilmann, O.; Beweries, T.; Roy, S.; Arndt, P.; Villinger, A.; Jemmis, E. D.; Schulz, A.; Rosenthal, U. J. Am. Chem. Soc. 2011, 133, 5463-5473
48. For reviews of nitriles, see: Michelin, R. A.; Mozzon, M.; Bertani, R. Coord. Chem. Rev. 1996, 147, 299-338 and references therein
49. Murahashi, S.-I.; Takaya, H. Acc. Chem. Res. 2000, 33, 225-233
50. Kukushkin, V. Y.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771-1802
51. Ferreira, M. J.; Martins, A. M. Coord. Chem. Rev. 2006, 250, 118-132
52. For examples of the insertion of nitriles into the M-X bond, see: Sun, X.; Wang, C.; Li, Z.; Zhang, S.; Xi, Z. J. Am. Chem. Soc. 2004, 126, 7172-7173
53. Zhang, W.-X.; Zhang, S.; Sun, X.; Nishiura, M.; Hou, Z.; Xi, Z. Angew. Chem., Int. Ed. 2009, 48, 7227-7231
54. Zhang, S.; Sun, X.; Zhang, W.-X.; Xi, Z. Chem.-Eur. J. 2009, 15, 12608-12617
55. Zhang, S.; Zhang, W.-X.; Xi, Z. Chem.-Eur. J. 2010, 16, 8419-8426
56. Zhang, S.; Zhang, W.-X.; Zhao, J.; Xi, Z. J. Am. Chem. Soc. 2010, 132, 14042-14045
57. Zhang, S.; Zhang, W.-X.; Zhao, J.; Xi, Z. Chem.-Eur. J. 2011, 17, 2442-2449
58. 2CHCN into the M-X bond, see: Dormond, A.; Elbouadili, A.; Moise, C. J. Org. Chem. 1989, 54, 3747-3748
59. Yu, Z.; Wittbrodt, J. M.; Xia, A.; Heeg., M. J.; Schlegel, H. B.; Winter, C. H. Organometallics 2001, 20, 4301-4303
60. Lee, J.; Lee, C.; Lee, S. S.; Kang, S. O.; Ko, J. Chem. Commun. 2001, 1730-1731
61. 2CHCN, see: Tellers, D. M.; Ritter, J. C. M.; Bergman, R. G. Inorg. Chem. 1999, 38, 4810-4818
62. Iravani, E.; Neumüller, B. Organometallics 2003, 22, 4129-4135
63. Fedushkin, I. L.; Morozov, A. G.; Rassadin, O. V.; Fukin, G. K. Chem.-Eur. J. 2005, 11, 5749-5757
64. Fedushkin, I. L.; Morozov, A. G.; Chudakova, V. A.; Fukin, G. K.; Cherkasov, V. K. Eur. J. Inorg. Chem. 2009, 4995-5003
65. Well-defined keteniminate species: Zarges, W.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 1392-1394
66. Langlotz, I.; Marsch, M.; Harms, K.; Boche, G. Z. Kristallogr. 1999, 214, 509-510
67. Fulton, J. R.; Sklenak, S.; Bouwkamp, M. W.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 4722-4737
68. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330-9331
69. Farwell, J. D.; Hitchcock, P. B.; Lappert, M. F.; Protchenko, A. V. Chem. Commun. 2005, 2271-2273
70. Honzícek, J.; Vinklárek, J.; Erben, M.; Strizík, L.; Císarová, I.; Padelková, Z. J. Organomet. Chem. 2009, 694, 4250-4255
71. Only a keteniminate titanium species was reported: Minko, Y. A.; Belina, N. V.; Sushev, V. V.; Fukin, G. K.; Bubnov, M. P.; Kornev, A. N. J. Organomet. Chem. 2007, 692, 4157-4160
72. For cleavage of the β,β′-C-C bond of zirconacyclopentadienes, see: Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874
73. Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540
74. Hara, R.; Xi, Z.; Kotora, M.; Kotora, M.; Xi, C.; Takahashi, T. Chem. Lett. 1996, 1003-1004
75. Liu, J.; Zhang, W.-X.; Guo, X.; Hou, Z.; Xi, Z. Organometallics 2007, 26, 6812-6820
76. Miller, A. D.; McBee, J. L.; Tilley, T. D. J. Am. Chem. Soc. 2008, 130, 4992-4999
77. Owsianik, K.; Zablocka, M.; Igau, A.; Majoral, J.-P.; Skowronska, A. Eur. J. Inorg. Chem. 2001, 1693-1697
78. Cadierno, V.; Zablocka, M.; Donnadieu, B.; Igau, A.; Majoral, J.-P.; Skowronska, A. Chem.-Eur. J. 2001, 7, 221-229
79. Choukroun, R.; Lorber, C.; Vendier, L. Organometallics 2007, 26, 3784-3790