Dichloro[l,l'-bis(diphenylphosphino)ferrocene]palladium-(II): An Effective Catalyst for Cross-Coupling of Secondary and Primary Alkyl Grignard and Alkylzinc Reagents with Organic Halides

Journal of the American Chemical Society

Volumn 106, Issue 1, 1984, Pages 158-163

  Hayashi, Tamio ^a   Konishi, Mitsuo ^a   Kobori, Yuji ^a   Kumada, Makoto ^a   Higuchi, Taiichi ^b   Hirotsu, Ken ^b  

^a KYOTO UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000488020     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00313a032     Document Type: Article

References (75)

1. Hayashi, T.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 21, 1871.
2. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
3. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
4. Kumada, M. Pure Appl. Chem. 1980, 52, 669.
5. Negishi, E. Acc. Chem. Res. 1982, 15, 340.
6. Tamao, K.; Kumada, M. “Carbon-Carbon Bond Formation by Transition Metal Catalyzed Coupling Reactions”; Elsevier: Amsterdam, in press.
7. Jolly, P. W. In “Comprehensive Organometallic Chemistry”; Wilkinson, G., Stone, F. G. A., Abel, E. W., Ed.; Pergamon Press: New York, 1982; Vol. 8., p 713.
8. Trost, B. M.; Verhoeven, T. R. Pergamon Press., Vol. 8.; p 799.
9. Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
10. Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915.
11. Okamura, H.; Miura, M.; Take:, H. Tetrahedron Lett. 1979, 43.
12. Wenkert, E.; Ferreire, T. W.; Michelotti, E. L. J. Chem. Soc., Chem. Commun. 1979, 637.
13. Trost, B. M.; Tanigawa, Y. J. Am. Chem. Soc. 1979, 101, 4743.
14. Okamura, H.; Miura, M.; Kosugi, K.; Takei, H. Tetrahedron Lett. 1980, 21, 87.
15. Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1980, 21, 2531.
16. Sato, M.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1609.
17. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449.
18. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001.
19. Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821.
20. King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc., Chem. Commun. 1977, 683.
21. King, A. O.; Negishi, E. J. Org. Chem. 1978, 43, 358.
22. Negishi, E.; Okukado, N.; King, A. O.; VanHorn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254.
23. Fauvarque, J.-F.; Jutand, A. J. Organomet. Chem. 1977, 132, C17.
24. Russell, C. E.; Hegedus, L. S. J. Am. Chem. Soc. 1983, 105, 943.
25. Negishi, E.; Baba, S. J. Chem. Soc., Chem. Commun. 1976, 596.
26. Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729.
27. Negishi, E.; VanHorn, D. E. J. Am. Chem. Soc. 1977, 99, 3168.
28. Okukado, N.; VanHorn, D. E.; Klima, W. L.; Negishi, E. Tetrahedron Lett. 1978, 1027.
29. Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408.
30. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833.
31. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
32. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
33. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 3437.
34. Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 867.
35. Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. 1981, 22, 127.
36. Tomao, K.; Kiso, Y.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9268.
37. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1973, 50, C12.
38. Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
39. Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180.
40. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minalo, A.; Kumada, M. Bull Chem. Soc. Jpn. 1976, 49, 1958.
41. Johnson, C. A. ORTEP-ll; Oak Ridge National Laboratory Report ORNL-3794 (2nd revision with supplemental instructions), 1971.
42. Steffen, W. L.; Palenik, G. J. Inorg. Chem. 1976, 15, 2432.
43. Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262.
44. Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7547.
45. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981.
46. Moravsky, A.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4182.
47. Bergstrom, D. E.; Ogawa, M. K. J. Am. Chem. Soc. 1978, 100, 8106.
48. Heck, R. F. “Organotransition Metal Chemistry. A Mechanistic Approach”; Academic Press: New York, 1974.
49. Whitesides, G. M.; Gaash, J. F.; Stedronsky, E. R. J. Am. Chem. Soc. 1972, 94, 5258.
50. Reger, D. L.; Culbertson, E. C. J. Am. Chem. Soc. 1976, 98, 2789.
51. Grubbs, R. H.; Miyashita, A.; Liu, M.; Burk, P. J. Am. Chem. Soc. 1978, 100, 2418.
52. Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933.
53. Loar, M. K.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4174.
54. Ozawa, F.; Ito, T.; Nakamura, Y.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1981, 54, 1868.
55. Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857.
56. Sanger, A. R. J. Chem. Soc., Dalton Trans. 1977, 1971.
57. Hayashi, T.; Konishi, M.; Kumada, M. J. Organomet. Chem. 1980, 186, C1.
58. Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1981, 313.
59. Pridgen, L. N.; Killmer, L. B. J. Org. Chem. 1981, 46, 5402.
60. Suzuki, A. 27th Symposium on Organometallic Chemistry, Tokyo, 1980, Abstract p 3.
61. Kobayashi, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1981, 333.
62. Cotton, F. A.; Faut, O. D.; Goodgame, D. M. L. J. Am. Chem. Soc. 1961, 83, 344.
63. Sandhu, S. S.; Gupta, M. Chem. Ind. (London) 1967, 1876.
64. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
65. Hartley, F. R. Organomet. Chem. Rev., Sect. A 1970, 6, 119.
66. Sugi, Y.; Bando, K. Chem. Lett. 1976, 727.
67. Braude, E. A.; Evans, E. A. J. Chem. Soc. 1956, 3333.
68. Dolby, L. J.; Wilkins, C.; Frey, T. G. J. Org. Chem. 1966, 31, 1110.
69. Bishop, J. J.; Davison, A.; Katcher, M. L.; Lichtenberg, D. W.; Merrill, R. E.; Smart, J. C. J. Organomet. Chem. 1971, 27, 241.
70. Pouchert, C. J.; Cambell, J. R. “The Aldrich Library of NMR Spectra”; Aldrich Chemical Company, Inc.: Milwaukee, WI, 1974; Vol. IV.
71. Moore, W. M.; Peters, D. G. J. Am. Chem. Soc. 1975, 97, 139.
72. Caubere, P.; Coudert, G. Tetrahedron 1972, 28, 5635.
73. Pino, P.; Lardicci, L.; Centoni, L. J. Org. Chem. 1959, 24, 1399.
74. Busing, W. R.; Martin, K. O.; Levy, H. A. orfls; Oak Ridge National Laboratory Report ORNL-TM-305, 1965.
75. Cromer, D. T.; Waber, J. T. “International Tables for X-ray Crystallography”; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.2A, p 72.