Combined experimental and computational investigation of the mechanism of nickel-catalyzed three-component addition processes

Organometallics

Volumn 23, Issue 20, 2004, Pages 4636-4646

  Hratchian, Hrant P ^a   Chowdhury, Sanjoy K ^a   Gutiérrez García, Víctor M ^a   Amarasinghe, Kande K D ^a   Heeg, Mary Jane ^a   Schlegel, H Bernhard ^a   Montgomery, John ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYSTS; ADDITION PROCESSES; ADDUCTS; CATALYTIC CYCLIZATIONS;

ADDITION REACTIONS; CATALYSTS; COMPUTATIONAL METHODS; OLIGOMERS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

NICKEL;

EID: 4944241519     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049471a     Document Type: Article

References (119)

1. (a) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
2. (b) Smith, A. K. In Comprehensive Organometallic Chemistry II; Puddephatt, R. J., Ed.; Pergamon Press: New York, 1995; Vol. 9, p 29.
3. (c) Montgomery, J. Organometallic Complexes of Nickel. In Science of Synthesis; Trost, B. M., Lautens, M., Eds.; Thieme: Stuttgart, Germany, 2001; Vol. 1, pp 11-62.
4. (d) Kaschube, W.; Schröder, W.; Pörschke, K. R.; Angermund, K.; Krüger, C. J. Organomet. Chem. 1990, 389, 399.
5. (e) Grubbs, R. H.; Miyashita, A. J. Am. Chem. Soc. 1978, 100, 1300.
6. (f) McKinney, R. J.; Thorn, D. L.; Hoffman, R.; Stockis, A. J. Am. Chem. Soc. 1981, 103, 2595.
7. (g) Büch, H. M.; Binger, P.; Benn, R.; Rufinska, A. Organometallics 1987, 6, 1130.
8. (h) Koo, K.; Hillhouse, G. L. Organometallics 1998, 17, 2924.
9. Maekawa, M.; Munakata, M.; Kuroda-Sowa, T.; Hachiya, K. Inorg. Chim. Acta 1996, 230, 249.
10. (a) Echavarren, A. M.; Castaño, A. M. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1998; Vol. 6, p 1.
11. (b) Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 174.
12. (c) Deming, T. J. J. Am. Chem. Soc. 1998, 120, 4240.
13. (d) Deming, T. J.; Curtin, S. A. J. Am. Chem. Soc. 2000, 122, 5710.
14. (a) Grubbs, R. H.; Miyashita, A.; Liu, M.; Burk, P. L. J. Am. Chem. Soc. 1977, 99, 3863.
15. (b) Grubbs, R. H.; Miyashita, A.; Liu, M.; Burk, P. L. J. Am. Chem. Soc. 1978, 100, 2418.
16. Carmona, E.; Gutiérrez-Puebla, E.; Marïn, J. M.; Menge, A.; Paneque, M.; Poveda, M. L.; Ruiz, C. J. Am. Chem. Soc. 1989, 111, 2883.
17. (a) Benn, R.; Büssemeier, B.; Holle, S.; Jolly, P. W.; Mynott, R.; Tkatchenko, I.; Wilke, G. J. Organomet. Chem. 1985, 279, 63.
18. (b) Keim, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 235.
19. (c) Wender, P. A.; Ihle, N. C. Tetrahedron Lett. 1987, 28, 2451.
20. (d) Wender, P. A.; Snapper, M. L. Tetrahedron Lett. 1987, 28, 2221.
21. (e) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904.
22. (f) Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089.
23. (g) Wender, P. A.; NUSS, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vagberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908.
24. (h) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678.
25. (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432.
26. (b) Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962.
27. (c) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843.
28. (d) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824.
29. (e) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255.
30. (a) Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T. Justus Liebigs Ann. Chem. 1948, 560, 1.
31. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
32. (c) Bhatarah, P.; Smith, E. H. J. Chem. Soc., Perkin Trans. 1 1992, 2163.
33. (d) Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133.
34. (e) Ikeda, S.; Watanabe, H.; Sato, Y. J. Org. Chem. 1998, 63, 7026.
35. (f) Shanmugasundaram, M.; Wu, M. S.; Jeganmohan, M.; Huang, C.-W.; Cheng, C.-H. J. Org. Chem. 2002, 67, 7724.
36. See also: (g) Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2002, 124, 15188.
37. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
38. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
39. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
40. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
41. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
42. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
43. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
44. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
45. For representative examples, see: (a) Montgomery, J. Ace. Chem. Res. 2000, 33, 467. (b) Ikeda, S. Ace. Chem. Res. 2000, 33, 511. (c) Sato, Y.; Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2000, 122, 1624. (d) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (f) Ezoe, A.; Kimura, M.; Inoue, T.; Mori, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2002, 41, 2784. (g) Miller, K. M.; Huang, W.S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442. (h) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
46. (a) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
47. (b) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775.
48. (c) Seo, J.; Chui, H. M. P.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476.
49. (d) Mahandru, G. M.; Skauge, A. R. L.; Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 13481.
50. (e) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1998, 61, 8248.
51. (f) Rayabarapu, D. K.; Sambaiah, T.; Cheng, C.-H. Angew. Chem., Int. Ed. 2001, 40, 1286.
52. (g) Rayabarapu, D. K.; Cheng, C.-H. Chem. Eur. J. 2003, 9, 3164.
53. (a) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30.
54. (b) See ref 9d for additional discussion of nickel enolates.
55. (a) Savchenko, A. V.; Montgomery, J. J. Org. Chem. 1996, 61, 1562.
56. (b) Montgomery, J.; Oblinger, E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911.
57. (a) For examples of Ni(0) complexes that possess and alkene and an alkyne unit, see: Pörschke, K.-R. J. Am. Chem. Soc. 1989, 111, 5691.
58. (b) For an example of a nickel(II) metallacycle derived from an alkene and an alkyne unit, see ref Id.
59. For example, compare ref 13a-c: (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
60. (b) Huang, W.-S.; Chan, J.; Jamison, T. F. Org. Lett. 2000, 2, 4221.
61. (c) Ni, Y.; Amarasinghe, K. K. D.; Montgomery, J. Org. Lett. 2002, 4, 1743. Also see:
62. Lozanov, M.; Montgomery, J. J. Am. Chem. Soc. 2002, 124, 2106.
63. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; GAUSSIAN 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
64. 2〉 of 0.212 and 0.046, respectively. Further, the eigenvalues of the orbital rotation Hessian are -0.009 568 9 and -0.001996 1 au, respectively. This indicates that none of the transition states have significant multireference character at this level of theory.
65. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
66. (b) Becke. A. D. J. Chem. Phys. 1998, 98, 5648.
67. (c) Lee, T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
68. (d) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
69. (e) Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
70. (f) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
71. (g) Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209.
72. (h) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 225.
73. (a) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214,
74. (b) Peng, C.; Schlegel, H. B. Isr. J. Chem. 1998, 33, 449.
75. (c) Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
76. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
77. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
78. (c) Hratchian, H. P.; Schlegel, H. B. J. Phys. Chem. A 2002, 106, 165.
79. (d) Hratchian, H. P.; Schlegel, H. B. J. Chem. Phys. 2004, 120, 9918-9924.
80. (e) Hratchian, H. P.; Schlegel, H. B. J. Chem. Theor. Comput., in press.
81. For a recent discussion of C- and O-tautomers of nickel enolates, see: Campora, J.; Maya, C. M.; Palma, P.; Carmona, E.; Gutiérrez-Puebla, E.; Ruiz, C. J. Am. Chem. Soc. 2003, 125, 1482.
82. For discussion of interactions of metal hydrides or metal alkyls with nickel in catalytic processes, see: (a) Lautens, M.; Ma, S.; Chui, P. J. Am. Chem. Soc. 1997, 119, 6478. (b) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 113, 11090. (c) Terao, J.; Oda, A.; Ikumi, A.; Nakamura, A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2003, 42, 3412. (d) Subburaj, K.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 11210. (e) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
83. For discussion of interactions of metal hydrides or metal alkyls with nickel in catalytic processes, see: (a) Lautens, M.; Ma, S.; Chui, P. J. Am. Chem. Soc. 1997, 119, 6478. (b) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 113, 11090. (c) Terao, J.; Oda, A.; Ikumi, A.; Nakamura, A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2003, 42, 3412. (d) Subburaj, K.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 11210. (e) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
84. For discussion of interactions of metal hydrides or metal alkyls with nickel in catalytic processes, see: (a) Lautens, M.; Ma, S.; Chui, P. J. Am. Chem. Soc. 1997, 119, 6478. (b) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 113, 11090. (c) Terao, J.; Oda, A.; Ikumi, A.; Nakamura, A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2003, 42, 3412. (d) Subburaj, K.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 11210. (e) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
85. For discussion of interactions of metal hydrides or metal alkyls with nickel in catalytic processes, see: (a) Lautens, M.; Ma, S.; Chui, P. J. Am. Chem. Soc. 1997, 119, 6478. (b) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 113, 11090. (c) Terao, J.; Oda, A.; Ikumi, A.; Nakamura, A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2003, 42, 3412. (d) Subburaj, K.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 11210. (e) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
86. For discussion of interactions of metal hydrides or metal alkyls with nickel in catalytic processes, see: (a) Lautens, M.; Ma, S.; Chui, P. J. Am. Chem. Soc. 1997, 119, 6478. (b) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 113, 11090. (c) Terao, J.; Oda, A.; Ikumi, A.; Nakamura, A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2003, 42, 3412. (d) Subburaj, K.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 11210. (e) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698.
87. (a) Kaschube, W.; Pörschke, K.-R.; Angermund, K.; Krüger, C.; Wilke, G. Chem. Ber. 1988, 121, 1921.
88. (b) Pörschke, K.-R.; Kleimann, W.; Tsay, Y.-H.; Krüger, C.; Wilke, G. Chem. Ber. 1990, 123, 1267.
89. (c) Jonas, K.; Pörschke, K.-R.; Krüger, C.; Tsay, Y.-H. Angew. Chem., Int. Ed. Engl. 1976, 15, 621.
90. (d) Pörschke, K.-R.; Jonas, K.; Wilke, G. Chem. Ber. 1988, 121, 1913.
91. (a) Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172.
92. (b) Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160.
93. (c) Ogoshi, S.; Yoshida, T.; Nishida, T.; Monta, M.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 1944.
94. (a) Carpenter, J. E.; Weinhold, F. J. Mol Struct. (THEOCHEM) 1988, 46, 41.
95. (b) Carpenter, J. E. Ph.D. Thesis, University of Wisconsin, 1987.
96. (c) Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
97. (d) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
98. (e) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1986, 53, 1736.
99. (f) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
100. (g) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
101. (h) Weinhold, F.; Carpenter, J. E. The Structure of Small Molecules and Ions, Plenum: Amsterdam, 1988, p 227.
102. For an analysis of molecular orbitals in dimethylzinc, see: Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2805.
103. (a) For an example of a Zn-Ni bond, see: Budzelaar, P. H. M.; Boersma, J.; van der Kerk, G. J. M. Organometallics 1985, 4, 680.
104. z2 orbital to a vacant orbital on Cd, see: Yamaguchi, T.; Yamazaki, F.; Ito, T. J. Am. Chem. Soc. 1999, 121, 7405.
105. (c) For a general discussion of transition-metal/main-group-metal bonding, see: Frenking, G. F. J. Organomet. Chem. 2001, 635, 9.
106. 10 metal reactivity, see: Stahl, S. S.; Thorman, J. L.; de Silva, N.; Guzei, I. A.; Clark, R. W. J. Am. Chem. Soc. 2003, 125, 12.
107. (a) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212.
108. (b) Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598.
109. (c) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
110. We are unaware of an exact precedent for this possibility. However, very different kinetic and thermodynamic cis/trans selectivities in the zirconocene-catalyzed cyclomagnesiation of dienes is well established: (a) Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. (b) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457.
111. We are unaware of an exact precedent for this possibility. However, very different kinetic and thermodynamic cis/trans selectivities in the zirconocene-catalyzed cyclomagnesiation of dienes is well established: (a) Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. (b) Taber, D. F.; Louey, J. P.; Wang, Y.; Nugent, W. A.; Dixon, D. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 9457.
112. (a) Ikeda, S.; Cui, D.-M.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 4712.
113. (b) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371.
114. (c) Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099.
115. (a) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
116. (b) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
117. (c) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
118. (d) Amatore, C.; Carré, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem. Ear. J. 1996, 2, 957.
119. 2: in Stille couplings was demonstrated to have a decelerating effect: Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212.