Synthesis and structure of η2-phosphonioalkene-palladium(0) complexes. A catalyst intermediate in the palladium-mediated synthesis of alkenylphosphonium halides

Organometallics

Volumn 17, Issue 4, 1998, Pages 676-682

  Huang, Chien Chih ^a   Duan, Jiun Pey ^a   Wu, Ming Yuan ^a   Liao, Fen Ling ^a   Wang, Sue Lein ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000810911     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970709n     Document Type: Article

References (61)

1. For examples: (a) Kim, J.-I.-I.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1981, 46, 1067. (b) Takano, S.; Samizu, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 1032. (c) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047. (d) Hegedus, L. S.; Holden, M. S. J. Org. Chem. 1986, 51, 1171.
2. For examples: (a) Kim, J.-I.-I.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1981, 46, 1067. (b) Takano, S.; Samizu, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 1032. (c) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047. (d) Hegedus, L. S.; Holden, M. S. J. Org. Chem. 1986, 51, 1171.
3. For examples: (a) Kim, J.-I.-I.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1981, 46, 1067. (b) Takano, S.; Samizu, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 1032. (c) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047. (d) Hegedus, L. S.; Holden, M. S. J. Org. Chem. 1986, 51, 1171.
4. For examples: (a) Kim, J.-I.-I.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1981, 46, 1067. (b) Takano, S.; Samizu, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 1032. (c) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047. (d) Hegedus, L. S.; Holden, M. S. J. Org. Chem. 1986, 51, 1171.
5. (a) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
6. (b) Mascareñas, J. L.; García, A. M.; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1992, 33, 7589.
7. (c) Hong, C, Y.; Kishi, Y. J. Am. Chem. Soc. 1991, 113, 9693.
8. (d) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
9. (a) Satoh, N.; Ishiyama, T.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1987, 60, 3471.
10. (b) Miyaura, N.; Satoh, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 3745.
11. (c) Hayashi, T.; Hagihara, T.; Katsuro, Y.; Kumada, M. Bull. Chem. Soc. Jpn. 1983, 56, 363.
12. (a) Fauvarque, J. F.; Jutand, A. J. Organomet. Chem. 1981, 209, 109.
13. (b) Negishi, E.; Matsushita, H.; Okukado, N. Tetrahedron Lett. 1981, 22, 2715.
14. (c) Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393.
15. (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
16. (b) Minato, A.; Suzuki, K.; Tamao, K.; Kumada, M. Tetrahedron Lett. 1984, 25, 83.
17. (a) Yamamura, M.; Moritani, I.; Murahashi, S. I. J. Organomet. Chem. 1975, 91, C39.
18. (b) Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408.
19. (a) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138.
20. (b) Magnus, P.; Annoura, H.; Harling, J. J. Org. Chem. 1990, 55, 1709.
21. (c) Butlin, R. J.; Holmes, A. B.; Mcdonald, E. Tetrahedron Lett. 1988, 29, 2989.
22. (a) Mukhedkar, A. J.; Green, M.; Stone, F. G. A. J. Chem. Soc. A 1969, 3023.
23. (b) Johnson, B. F. G.; Lewis, J.; Jones, J. D.; Taylor, K. A. J. Chem. Soc., Datlon Trans. 1974, 34.
24. (c) Mukhedkar, V. A.; Mukhedkar, A. J. J. Inorg. Nucl. Chem. 1981, 43, 2801.
25. (d) Otsuka, S.; Ataka, K. J. Chem. Soc., Dalton Trans. 1976, 327.
26. (e) Frizuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1979, 101, 3043.
27. (f) Onishi, M.; Yamamoto, H.; Hiraki, K. Bull. Chem. Soc. Jpn. 1978, 51, 1856.
28. Rybin, L. V.; Petrovskaya, E. A.; Rubinskaya, M. I.; Kuz'mina, L. G.; Struchkov, Y. T.; Kaverin, V. V.; Koneva, N. Y. J. Organomet. Chem. 1985, 288, 119.
29. (a) Kong, K.-C.; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313.
30. (b) Segelstein, B. E.; Butler, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12.
31. (c) Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576.
32. (d) Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937.
33. Loar, M. K.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4174.
34. (a) Ozawa, F.; Ito, T.; Nakamura, Y.; Yamamoto, A. J. Organomet. Chem. 1979, 168, 375.
35. (b) Ito, T.; Hasegawa, S.; Takahashi, Y.; Ishii, Y. J. Organomet. Chem. 1974, 73, 401.
36. (c) Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
37. (d) Minematsu, H.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1975, 91, 389.
38. (e) Minematsu, H.; Nonaka, Y.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1973, 59, 395.
39. (f) Green, M.; Howard, J. A. K.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1977, 271.
40. (a) Tolman, C. A.; Seidel, W. C.; Gerlach, D. H. J. Am. Chem. Soc. 1972, 94, 2669.
41. (b) Cheng, P. T.; Cook, C. D.; Nyburg, S. C.; Wan, K. Y. Inorg. Chem. 1971, 10, 2210.
42. Cheng, P. T.; Cook, C. D.; Koo, C. H.; Nyburg, S. C.; Shiomi, M. T. Acta Crystallogr. 1971, B27, 1904.
43. (a) Rösch, N.; Hoffmann, R. Inorg. Chem. 1974, 13, 2656.
44. (b) Åkermark, B.; Almemark, M.; Almlöf, J.; Bäckvall, J. E.; Roos, B.; Stegard, Å. J. Am. Chem. Soc. 1977, 99, 4617.
45. Scordia, H.; Kergoat, R.; Kubicki, M. M.; Guerchais, J. Organometallics 1983, 2, 1681.
46. (a) Ebsworth, E. A. V.; Fraser, T. E.; Rankin, D. W. H. Chem. Ber. 1977, 110, 3494.
47. (b) Klebach, T. C.; Lourens, R.; Bickelhaupt, F.; Stam, C. H.; Van Herk, A. J. Organomet. Chem. 1981, 210, 211.
48. (c) Pickering, R. A.; Jacobson, R. A. Angelici, R. J. J. Am. Chem. Soc. 1981, 103, 817.
49. (d) Voran, S.; Blau, H.; Malisch, W.; Schubert, U. J. Organomet. Chem. 1982, 232, C33.
50. (e) Antonova, A. B.; Kovalenko, S. V.; Korniyets, E. D.; Johansson, A. A.; Struchkov, Y. T.; Ahmedov, A. I.; Yanovsky, A. I. J. Organomet. Chem. 1983, 244, 35.
51. Lai, C. H.; Cheng, C. H.; Chou, W. C.; Wang, S. L. Orgonometallics 1993, 12, 1105.
52. (a) Verkade, J. G.; Quin, L. D. Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis: Organic Compounds and Metal Complexes; VCH: Deerfield Beach, FL, 1987.
53. (b) Gorenstein, D. G. Phosphorus-31 NMR: Principles and Applications; Academic Press: Orlando, FL, 1984.
54. 2(CH=CHPh)Br changed with reaction time with the former increased in relative concentration as the reaction proceeded.
55. Seyferth, D.; Fogel, J. J. Organomet. Chem. 1966, 6, 205.
56. Migita, T.; Nagai, T.; Kiughi, K.; Kosugi, M. Bull. Chem. Soc. Jpn. 1983, 56, 2869.
57. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
58. Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. J. Chem. Soc. D 1970, 1065.
59. Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287.
60. Roger, D. Acta Crystallogr. 1981, A37, 734.
61. Atomic scattering factors were obtained from the following: International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. IV.