Insertions of unsymmetric alkynes into the metal-carbon bonds of nickelacycles: What determines the regiochemistry?

Helvetica Chimica Acta

Volumn 84, Issue 10, 2001, Pages 3084-3104

  Bennett, Martin A ^a   Macgregor, Stuart A ^b   Wenger, Eric ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; NICKEL; TRANSITION METALS;

ALKANYES;

SYNTHESIS (CHEMICAL);

CARBON; METAL COMPLEX; NICKEL COMPLEX; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ISOMERISM; KINETICS; STEREOCHEMISTRY;

EID: 0035191738     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20011017)84:10<3084::AID-HLCA3084>3.0.CO;2-H     Document Type: Article

References (81)

1. L. S. Boffa, B. M. Novak, Chem. Rev. 2000, 100, 1479.
2. S. D. Ittel, L. K. Johnson, M. Brookhart, Chem. Rev. 2000, 100, 1169.
3. M. Torrent, M. Solà, G. Frenking, Chem. Rev. 2000, 100, 439.
4. P. M. Maitlis, Pure Appl. Chem. 1972, 30, 427.
5. P. M. Maitlis, Pure Appl. Chem. 1973, 33, 489.
6. P. M. Maitlis, Acc. Chem. Res. 1976, 9, 93.
7. P. M. Maitlis, J. Organomet. Chem. 1980, 200, 161.
8. P. W. Jolly, in 'Comprehensive Organometallic Chemistry', Eds. G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon, Oxford, 1982, Vol. 8, p. 649.
9. M. I. Bruce, Angew. Chem., Int. Ed. 1977, 16, 73.
10. I. Omae, 'Organometallic Intramolecular Coordination Compounds', Organometallic Chemistry Library No 18, Elsevier, Amsterdam, 1986.
11. A. D. Ryabov, Chem. Rev. 1990, 90, 403.
12. A. D. Ryabov, Synthesis 1985, 233.
13. E. Lindner, Adv. Heterocycl. Chem. 1986, 39, 237.
14. M. Pfeffer, Recl. Trav. Chim. Pays-Bas 1990, 109, 567.
15. R. F. Heck, G. Wu, W. Tao, A. L. Rheingold, in 'Catalysis of Organic Reactions', Ed. D. W. Blackburn, Dekker, New York, 1990.
16. J. Spencer, M. Pfeffer, in 'Advances in Metal-Organic Chemistry', Ed. L. S. Liebeskind, JAI Press, Stamford, 1998, Vol. 6, p. 104.
17. S. Cacchi, J. Organomet. Chem. 1999, 576, 42.
18. R. C. Larock, J. Organomet. Chem. 1999, 576, 111.
19. L. S. Liebeskind, J. R. Gasdaska, J. S. McCallum, S. J. Tremont, J. Org. Chem. 1989, 54, 669.
20. L. Main, B. K. Nicholson, in 'Advances in Metal-Organic Chemistry', Ed. L. S. Liebeskind, JAI Press, Stamford, 1994, Vol. 3, p. 1.
21. F. Kakiuchi, Y. Yamamoto, N. Chatani, S. Murai, Chem. Lett. 1995, 681.
22. M. Martinez, G. Muller, D. Panyella, M. Rocamora, X. Solans, M. Font-Bardía, Organometallics 1995, 14, 5552.
23. E. G. Samsel, J. R. Norton, J. Am. Chem. Soc. 1984, 106, 5505.
24. J. M. Huggins, R. G. Bergman, J. Am. Chem. Soc. 1981, 103, 3002.
25. P. de Vaal, A. Dedieu, J. Organomer. Chem. 1994, 478, 121.
26. A. D. Ryabov, R. van Eldik, G. Le Borgne, M. Pfeffer, Organometallics 1993, 12, 1386.
27. W. Ferstl, I. K. Sakodinskaya, N. Beydoun-Sutter, G. Le Borgne, M. Pfeffer, A. D. Ryabov, Organometallics 1997, 16, 411.
28. J.-A. Abad, Gazz. Chim. Ital. 1997, 127, 119.
29. J. Spencer, M. Pfeffer, N. Kyritsakas, J. Fischer, Organometallics 1995, 14, 2214.
30. M. A. Bennett, E. Wenger, Organometallics 1995, 14, 1267.
31. A. K. Smith, in 'Comprehensive Organometallic Chemistry II', Eds. E. W. Abel, F. G. A. Stone, G. Wilkinson, and R. J. Puddephatt, Elsevier, Oxford, 1995, Vol. 9, p. 29.
32. J. Cámpora, P. Palma, E. Carmona, Coord. Chem. Rev. 1999, 193-195, 207.
33. A. M. Echavarren, A. M. Castaño, in 'Advances in Metal-Organic Chemistry', Ed. L. S. Liebeskind, JAI Press, Stamford, 1998, Vol. 6, p. 1.
34. J. Cámpora, M. Paneque, M. L. Poveda, E. Carmona, Synlett 1994, 465.
35. M. A. Bennett, H. P. Schwemlein, Angew. Chem., Int. Ed. 1989, 28, 1296.
36. M. A. Bennett, E. Wenger, Chem. Ber. Recl. 1997, 130, 1029.
37. W. M. Jones, J. Klosin, Adv. Organomet. Chem. 1998, 42, 147.
38. G. Muller, D. Panyella, M. Rocamora, J. Sales, M. Font-Bardía, X. Solans, J. Chem. Soc., Dalton Trans. 1993, 2959.
39. A. J. Edwards, S. A. Macgregor, A. D. Rae, E. Wenger, A. C. Willis, Organometallics 2001, 20, 2864.
40. S. A. Macgregor, E. Wenger, Organometallics, submitted.
41. F. Maassarani, M. Pfeffer, G. Le Borgne, Organometallics 1987, 6, 2029.
42. J. Dupont, M. Pfeffer, J. Organomet. Chem. 1987, 321, C13.
43. J. Spencer, M. Pfeffer, A. DeCian, J. Fischer, J. Org. Chem. 1995, 60, 1005.
44. H.-F. Klein, L. Reitzel, Chem. Ber. 1988, 121, 1115.
45. E. Carmona, E. Gutiérrez-Puebla, A. Monge, J. M. Marin, M. Paneque, M. L. Poveda, Organometallics 1984, 3, 1438;
46. E. Carmona, E. Gutiérrez-Puebla, A. Monge, J. M. Marin, M. Paneque, M. L. Poveda, Organometallics 1989, 8, 967.
47. M. Hada, Y. Tanaka, M. Ito, M. Murakami, H. Amii, Y. Ito, H. Nakatsuji, J. Am. Chem. Soc. 1994, 116, 8754.
48. N. Koga, K. Morokuma, Chem. Rev. 1991, 91, 823.
49. A. Dedieu, Chem. Rev. 2000, 100, 543.
50. S. Niu, M. B. Hall, Chem. Rev. 2000, 100, 353.
51. J. Browning, M. Green, B. R. Penfold, J. L. Spencer, F. G. A. Stone, J. Chem. Soc., Chem. Commun. 1973, 31;
52. J. Browning, M. Green, J. L. Spencer, F. G. A. Stone, J. Chem. Soc., Dallon Trans. 1974, 97;
53. H. C. Clark, A. Shaver, Can. J. Chem. 1975, 53, 3462.
54. E. Carmona, P. Palma, M. Paneque, M. L. Poveda, E. Gutiérrez-Puebla, A. Monge, J. Am. Chem. Soc. 1986, 108, 6424.
55. E. Carmona, E. Gutiérrez-Puebla, J. M. Marín, A. Monge, M. Paneque, M. L. Poveda, C. Ruiz, J. Am. Chem. Soc. 1989, 111, 2883.
56. J. Cámpora, A. Llebaria, J. M. Moretó, M. L. Poveda, E. Carmona, Organometallics 1993, 12, 4032.
57. J. Cámpora, E. Carmona, P. Palma, M. L. Poveda, J. Chem. Soc., Perkin Trans. 1 1990, 180.
58. K. Koo, G. L. Hillhouse, Organometallics 1995, 14, 4421.
59. K. Koo, G. L. Hillhouse, A. L. Rheingold, Organometallics 1995, 14, 456.
60. K. Koo, G. L. Hillhouse, Organometallics 1996, 15, 2669.
61. M. A. Bennett, T. W. Hambley, N. K. Roberts, G. B. Robertson, Organometallics 1985, 4, 1992.
62. M. A. Bennett, M. Glewis, D. C. R. Hockless, E. Wenger, J. Chem. Soc., Dalton Trans. 1997, 3104.
63. M. A. Bennett, E. Wenger, Organometallics 1996, 15, 5536.
64. M. A. Bennett, D. C. R. Hockless, E. Wenger, Organometallics 1995, 14, 2091.
65. M. Catellani, B. Marmiroli, M. C. Fagnola, D. Acquotti, J. Organomet. Chem. 1996, 507, 157.
66. T. Tsuda, H. Mizuno, A. Takeda, A. Tobisawa, Organometallics 1997, 16, 932.
67. M. A. Bennett, C. J. Cobley, E. Wenger, A. C. Willis, Chem. Commun. 1998, 1307.
68. M. A. Bennett, C. J. Cobley, A. D. Rae, E. Wenger, A. C. Willis, Organometallics 2000, 19, 1522.
69. A. Altomare, M. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
70. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, The DIRDIF-94 Program System, Technical Report of the Crystallographic Laboratory, University of Nijmegen, The Netherlands, 1994.
71. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Eds. C. W. Carter Jr. and R. M. Sweet, Academic Press, New York, 1997, Vol. 276, p. 307.
72. TEXSAN: Single Crystal Structure Analysis Software, Vers. 1.8, Molecular Structure Corp., 3200 Research Forest Drive, The Woodlands TX 77381, USA, 1997.
73. E. J. Baerends, D. E. Ellis, P. Ros, Chem. Phys. 1973, 2, 41;
74. G. te Velde, E. J. Baerends, J. Comput. Phys. 1992, 99, 84;
75. C. Fonseca Guerra, J. G. Snijders, G. te Velde, E. J. Baerends, Theor. Chem. Acc. 1998, 99, 391.
76. A. D. Becke, Phys. Rev. A 1988, 38, 3098.
77. J. P. Perdew, Phys. Rev. B 1986, 33, 8822.
78. J. G. Snijders, E. J. Baerends, P. Ros, Mol. Phys. 1979, 38, 1909;
79. T. Ziegler, V. Tschinke, E. J. Baerends, J. G. Snijders, W. Ravenek, J. Phys. Chem. 1989, 93, 3050;
80. E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1993, 99, 4597.
81. L. Versluis, T. Ziegler, J. Chem. Phys. 1988, 88, 322.