Electrophile (H+, Me+)-mediated carbon-carbon bond formation between η3-allyl and alkynyl groups coordinated to "Cp*Ir"

Organometallics

Volumn 18, Issue 11, 1999, Pages 2210-2215

  Chin, Chong Shik ^a   Maeng, Wangho ^a   Chong, Daesung ^a   Won, Gyongshik ^a   Lee, Byeongno ^a   Park, Young Ja ^b   Shin, Jung Mi ^b  

^a Sogang University   (South Korea)

^b Sookmyung Women's University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001585058     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9900770     Document Type: Article

References (61)

1. (a) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272.
2. (b) Ipaktschi, J.; Mirzaei, F.; Demuth-Eberle, G. J.; Beck, J.; Serafin, M. Organometallics 1997, 16, 3965.
3. (c) Ipaktschi, J.; Demuth-Eberle, G. J.; Mirzaei, F.; Muller, B. G.; Beck, J.; Serafin, M. Organometallics 1995, 14, 3335.
4. (d) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
5. (e) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1994, 116, 11570.
6. (f) Ikeda, S.; Cui, D.-M.; Sato, Y. J. Org. Chem. 1994, 59, 6877.
7. (g) Trost, B. M.; Indolese, A. J. Am. Chem. Soc. 1993, 115, 4361.
8. (h) Barrado, G.; Hricko, M. M.; Miguel, D.; Riera, V.; Wally, H. Organometallics 1998, 17, 820.
9. (i) Camps, F.; Coll, J.; Moreto, J. M.; Torras, J. J. Org. Chem. 1989, 54, 1969.
10. (a) Shul'pin, G. B.; Shilov, A. E. Chem. Rev. 1997, 97, 2879.
11. (b) Bell, T. W.; Brough, S.-A.; Partridge, M. G.; Perutz, R. N.; Rooney, A. D. Organometallics 1993, 12, 2933.
12. (c) Brookhart, M.; Hauptman, E. J. Am. Chem. Soc. 1992, 114, 4437.
13. (d) Moseley, K.; Kang, J. W.; Maitlis, P. M. J. Chem. Soc. (A) 1970, 2875.
14. (e) Wakefield, J. B.; Stryker, J. M. Organometallics 1990, 9, 2428.
15. (f) Ritter, J. C. M.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 2580.
16. (g) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517.
17. McGhee, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 4246.
18. (a) Mirabelli, M. G. L.; Sneddon, L. G. J. Am. Chem. Soc. 1988, 110, 449.
19. (b) Ara, I.; Berenguer, J. R.; Eguizabal, E.; Fornies, J.; Lalinde, E.; Martin, A.; Martinez, F. Organometallics 1998, 17, 4578, and references therein.
20. (a) Tajden, E. B.; Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1992, 114, 1100.
21. (b) Tjaden, E. B.; Stryker, J. M. Organometallics 1992, 11, 16.
22. (c) Tajden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420.
23. (d) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 11, 600.
24. (e) Wakefield, J. M.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
25. Older, C. M.; Stryker, J. M. Organometallics 1998, 17, 5596.
26. (a) Chang, S.; Yoon, J.; Brookhart, M. J. Am. Chem. Soc. 1994, 116, 1869.
27. (b) Simpson R. D. Organometallics 1997, 16, 1797.
28. (a) de los Rios, I.; Tenorio, M. J.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
29. (b) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276.
30. (c) Kelly, C.; Lugan, M. R.; Geoffroy G. L.; Haggerty, B. S.; Rheingold, A. L. J. Am. Chem. Soc. 1992, 114, 6735.
31. (d) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585.
32. (e) O'Connor, J. M.; Hiibner, K. Chem. Commun. 1995, 1209.
33. (f) Wakatsuki, Y.; Koga, N.; Yamazaki, H.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 8105.
34. (g) McMullen, A. K.; Selegue, J. P.; Wang, J.-G. Organometallics 1991, 10, 3421.
35. (h) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 3697.
36. (i) Jia, G.; Xia, H. P.; Wu, W. F.; Ng, W. S. Organometallics 1996, 15, 3634.
37. (a) Gilbert, T. M.; Bergman, R. G. Organometallics 1983, 2, 1458.
38. (b) Fernandez, M.-J.; Maitlis, P. M. Organometallics 1983, 2, 164.
39. (c) Gilbert, T. M.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107, 3508.
40. (d) Fernandez, M.-J.; Maitlis, P. M. J. Chem. Soc., Dalton. Trans. 1984, 2063.
41. (e) Isobe, K.; Miguel, A. V.; Nutton, A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1984, 929.
42. (a) Vicic, D. A.; Jones, W. D. Organometallics 1997, 16, 1912.
43. (b) Bianchini, C.; Meli, A. J. Chem. Soc., Dalton Trans. 1996, 801.
44. (c) Alaimo, P. J.; Arndtsen, B. A.; Bergman, R. G. J Am. Chem. Soc. 1997, 119, 5269.
45. (d) Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970.
46. (a) Strout, D. L.; Zaric, S.; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068.
47. (b) Niu, S.; Zaric, S.; Bayse, C. A.; Strout, D. L.; Hall, M. B. Organometallics 1998, 17, 5139.
48. Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Frediani, P.; Herrera, V.; Sanchez-Delgado, R. A. J. Am. Chem. Soc. 1993, 115, 2731, and references therein.
49. (a) Wolf, J.; Werner, H. Organometallics 1987, 6, 1164.
50. (b) Casey, C. P.; Brady, J. T.; Boller, T. M.; Weinhold, F.; Hayashi, R. K. J. Am. Chem. Soc. 1998, 120, 12500.
51. (c) Casey, C. P.; Brady, J. T. Organometallics 1998, 17, 4620.
52. (d) van der Ent, A.; Onderdelinden, A. L. Inorg. Chim. Acta 1973, 7, 203.
53. Gamasa, M. P.; Gimeno, J.; Martin-Vaca, B. M. Organometallics 1998, 17, 3707.
54. 2-CH=CHPh) and the geometric isomer of 3H, respectively.
55. 1H NMR spectra showed that the products contained deuterium at five different carbons of 6H with different % of D, and mass spectra also showed various isotopomers.
56. Jeong, H.; Joo, K.-S.; Chin, C. S. Bull. Korean Chem. Soc. 1997, 18, 402.
57. (a) Kang, J. W.; Mosely, K.; Maitlis, P. M. J. Am. Chem. Soc. 1969, 91, 5970.
58. (b) Ball, R. G.; Graham, W. A. G.; Heinekey, D. M.; Hoyano, J. K.; McMaster, A. D.; Mattson, B. M.; Michel, S. T. Inorg. Chem. 1990, 29, 2023.
59. (c) Heinekey, D. M.; Chinn, M. S. J. Am. Chem. Soc. 1990, 112, 5166.
60. (d) Churchill, M. R.; Julis, S. A. Inorg. Chem. 1979, 18, 1215.
61. (e) White, C.; Thomson, S. T.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1977, 1305.