Transition metal-catalyzed carbon-carbon bond formation with Grignard reagents - Novel reactions with a classic reagent

European Journal of Organic Chemistry

Volumn , Issue 10, 2004, Pages 2081-2091

  Shinokubo, Hiroshi ^a,b   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Chromium; Cobalt; Grignard reagent; Iron; Manganese

Indexed keywords

CARBON; CHROMIUM; COBALT; IRON; MANGANESE; REAGENT; TRANSITION ELEMENT;

CATALYST; CHEMICAL BOND; GRIGNARD REACTION; SHORT SURVEY; SYNTHESIS;

EID: 2442700920     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300757     Document Type: Short Survey

References (117)

1. [1a] B. J. Wakefield, Organomagnesium Methods in Organic Synthesis, Academic Press, London, 1995.
2. [1b] Handbook of Grignard-Reagents (Eds.: G. S. Silverman, P. E. Rakita), Marcel Dekker, New York, 1996.
3. [1c] Grignard Reagents New Development (Ed.: H. G. Richey, Jr.), Wiley, Chichester, 2000.
4. [2a] V. Grignard, C. R. Hebd. Seances Acad. Sci. 1900, 130, 1322.
5. [2b] V. Grignard, Ann. Chim. 1901, 24, 433.
6. P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. Int. Ed. 2003, 42, 4302.
7. [4a] K. Maruyama, T. Katagiri, J. Am. Chem. Soc. 1986, 108, 6263.
8. [4b] E. C. Ashby, J. R. Bowers Jr., J. Am. Chem. Soc. 1981, 103, 2242.
9. [4c] F. F. Blicke, L. D. Powers, J. Am. Chem. Soc. 1929, 51, 3378.
10. [4d] J. F. Fauvarque, E. Rouget, C. R. Acad. Sci. Ser. C 1968, 267, 1355.
11. [4e] T. Crossland, T. Holm, Acta Chem. Scand. 1971, 25, 29.
12. [4f] H. Yamataka, T. Matsuyama, T. Hanafusa, J. Am. Chem. Soc. 1989, 111, 4912.
13. [4g] K. Maeda, H. Shinokubo, K. Oshima, J. Org. Chem. 1996, 61, 6770.
14. [4h] A. Inoue, H. Shinokubo, K. Oshima, Synlett 1999, 1582.
15. [5a] M. S. Kharasch, O. Reinmuth, Grignard Reactions of Nonmetallic Substances, Prentice Hall, New York, 1954.
16. [5b] M. S. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316.
17. [5c] M. S. Kharasch, W. Nudenberg, S. Archer, J. Am. Chem. Soc. 1943, 65, 495.
18. [5d] J. K. Kochi, J. Organomet. Chem. 2002, 653, 11.
19. [6a] R. J. P. Corriu, J. P. Masse, J. Chem. Soc., Chem. Commun. 1972, 144.
20. [6b] K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374.
21. [6c] K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, M. Kumada, Bull. Chem. Soc. Jpn. 1976, 49, 1958.
22. [7a] G. Cahiez, An. Quim. 1995, 91, 561.
23. [7b] J. F. Normant, G. Cahiez, in Modem Synthetic Methods, Vol. 3 (Ed.: R. Scheffold), Otto Salle Verlag, Frankfurt am Main, 1983, p. 173.
24. [8a] M. Hojo, H. Harada, H. Ito, A. Hosomi, J. Am. Chem. Soc. 1997, 119, 5459.
25. [8b] M. Hojo, H. Harada, H. Ito, A. Hosomi, Chem. Commun. 1997, 2077.
26. [8c] M. Hojo, R. Sakuragi, Y. Murakami, Y. Baba, A. Hosomi, Organometallics 2000, 19, 4941.
27. [9a] G. Cahiez, M. Alami, Tetrahedron Lett. 1989, 30, 3541.
28. [9b] M. Alami, S. Marquais, G. Cahiez, Org. Synth. 1993, 72, 135.
29. [10a] J. F. Normant, A. Alexakis, Synthesis 1981, 841.
30. [10b] W. Oppolozer, Angew. Chem. Int. Ed. Engl. 1989, 28, 38.
31. [10c] E. Negishi, Pure Appl. Chem. 1981, 53, 2333.
32. [10d] P. Knochel, in Comprehensive Organometallic Chemistry II (Eds.: E. W. Able, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, vol. 11, p. 159.
33. [10e] P. Knochel, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, vol. 4, p. 865.
34. [10f] Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207.
35. [10g] E. Negishi, D. Y. Kondakov, Chem. Rev. 1996, 96, 417.
36. [10h] I. Marek, J. F. Normant, in Metal Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, p. 271.
37. Zirconium-catalyzed carbometallation of the C=C bond using Grignard reagents has been very successful. See: [11a] A. H. Hoveyda, in Titanium and Zirconium in Organic Synthesis (Ed.: I. Marek), John Wiley & Sons, 2002, p. 180.
38. [11b] E. Negishi, T. Takahashi, Synthesis 1988, 1.
39. [11c] U. M. Dzhemilev, O. S. Vostrikova, G. A. Tolstikov, J. Organomet. Chem. 1986, 304, 17.
40. [11d] E. Negishi, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, vol. 4, p. 1163.
41. [12a] H. Shinokubo, K. Oshima, J. Synth. Org. Chem. Jpn. 1999, 57, 27.
42. [12b] H. Shinokubo, K. Oshima, Catalysis Surveys from Asia 2003, 7, 39.
43. T. Nishikawa, H. Shinokubo, K. Oshima, Org. Lett. 2003, 5, 4623.
44. P. Kocienski, C. Barber, Pure Appl. Chem. 1990, 62, 1933.
45. [15a] R. W. Hoffmann, O. Knopff, A. Kusche, Angew. Chem. Int. Ed. 2000, 39, 1462.
46. [15b] R. W. Hoffmann, B. Hölzer, O. Knopff, K. Harms, Angew. Chem. Int. Ed. 2000, 39, 3072.
47. [15c] A. Inoue, J. Kondo, H. Shinokubo, K. Oshima, Chem. Eur. J. 2002, 8, 1730.
48. [15d] A. Inoue, J. Kondo, H. Shinokubo, K. Oshima, Chem. Lett. 2001, 956.
49. [15e] J. Kondo, A. Inoue, H. Shinokubo, K. Oshima, Angew. Chem. Int. Ed. 2001, 40, 2085.
50. [16a] A. Sidduri, M. J. Rozema, P. Knochel, J. Org. Chem. 1993, 58, 2694.
51. [16b] A. Sidduri, P. Knochel, J. Am. Chem. Soc. 1992, 114, 7579.
52. [16c] A. Shibli, J. P. Varghese, R Knochel, I. Marek, Synlett 2001, 818.
53. [16d] A. Oku, T. Harada, T. Katsuhira, H. Wada, A. Osada, Pure Appl. Chem. 1996, 68, 649.
54. [16e] T. Harada, T. Katsuhira, D. Hara, Y. Kotani, K. Maejima, R. Kaji, A. Oku, J. Org. Chem. 1993, 58, 4897.
55. [16f] T. Harada, T. Katsuhira, K. Hattori, A. Oku, J. Org. Chem. 1993, 58, 2958.
56. [16g] T. Harada, K. Hattori, T. Katsuhira, A. Oku, Tetrahedron Lett. 1989, 30, 6035.
57. [16h] T. Harada, Y. Kotani, T. Katsuhira, A. Oku, Tetrahedron Lett. 1991, 32, 1573.
58. [16i] T. Katsuhira, T. Harada, A. Osada, K. Maejima, A. Oku, J. Org. Chem. 1993, 58, 6166.
59. [16j] T. Harada, T. Kaneko, T. Fujiwara, A. Oku, J. Org. Chem. 1997, 62, 8966.
60. [17a] R. L. Danheiser, A. C. Savoca, J. Org. Chem. 1985, 50, 2401.
61. [17b] D. S. Maltesen, D. Majumdar, J. Am. Chem. Soc. 1980, 102, 7588.
62. [18a] G. H. Posner, G. L. Loomis, H. S. Sawaya, Tetrahedron Lett. 1975, 16, 1373.
63. [18b] K. Kitatani, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 1976, 98, 2362.
64. [18c] K. Kitatani, H. Hiyama, H. Nozaki, Bull. Chem. Soc. Jpn. 1977, 50, 1600.
65. [18d] K. Kitatani, H. Yamamoto, H. Hiyama, H. Nozaki, Bull. Chem. Soc. Jpn. 1977, 50, 2158.
66. [19a] R. Inoune, H. Shinokubo, K. Oshima, Tetrahedron Lett. 1996, 37, 5377.
67. [19b] H. Kakiya, R. Inoue, H. Shinokubo, K. Oshima, Tetrahedron 2000, 56, 2131.
68. R. Inoue, H. Shinokubo, K. Oshima, J. Org. Chem. 1998, 63, 910.
69. [21a] H. Kakiya, R. Inoue, H. Shinokubo, K. Oshima, Tetrahedron Lett. 1997, 38, 3275.
70. [21b] H. Kakiya, H. Shinokubo, K. Oshima, Bull. Chem. Soc. Jpn. 2000, 73, 2139.
71. Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001.
72. [22b] C. P. Jasperse, D. P. Curran, T. L. Fevig, Chem. Rev. 1991, 91, 1237.
73. [23a] A Studer, S. Amrein, Synthesis 2002, 835.
74. [23b] P. A. Baguley, J. C. Walton, Angew. Chem. Int. Ed. 1998, 37, 3072.
75. [24a] J. Nakao, R. Inoue, H. Shinokubo, K. Oshima, J. Org. Chem. 1997, 62, 1910.
76. [24b] R. Inoue, J. Nakao, H. Shinokubo, K. Oshima, Bull Chem. Soc. Jpn. 1997, 70, 2039.
77. G. Cahiez, F. Lepifre, P. Ramiandrasoa, Synthesis 1999, 2138.
78. M. Alami, P. Ramiandrasoa, G. Cahiez, Synlett 1998, 325.
79. [27a] A Fürstner, Chem. Rev. 1999, 99, 991.
80. [27b] N. A. Saccomano, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York, 1991, vol. 1, chapter 1.6, p. 173.
81. [27c] K. Takai, in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), John Wiley & Sons, New York, 1995, p. 1266.
82. [28a] S. G. Davies, S. J. Coote, C. L. Goodfellow, in Advances in Metal-Organic Chemistry Vol. 2 (Ed.: L. S. Liebeskind), JAI Press, London, 1991, p. 1.
83. [28b] M. Uemura, in Advances in Metal-Organic Chemistry, Vol. 2 (Ed.: L. S. Liebeskind), JAI Press, London, 1991, p. 195.
84. [28c] M. F. Semmelhack, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York, 1991, vol. 4, chapter 2.4, p. 517.
85. [29a] M. Hojo, R. Sakuragi, S. Okabe, A. Hosomi, Chem. Commun. 2001, 357.
86. [29b] M. Hojo, K. Sakata, N. Ushioda, T. Watanabe, H. Nishikori, A. Hosomi, Organometallics 2001, 20, 5014.
87. [29c] M. Hojo, K. Sakata, M. Xiamuxikamaer, J. Ueno, H. Nishikori, A. Hosomi, Chem. Lett. 2002, 142.
88. T. Nishikawa, H. Kakiya, H. Shinokubo, K. Oshima, J. Am. Chem. Soc. 2001, 123, 4629.
89. [31a] K. E. Schwiebert, J. M. Stryker, J. Am. Chem. Soc. 1995, 117, 8275.
90. [31b] T. L. Dzwiniel, N. Etkin, J. M. Stryker, J. Am. Chem. Soc. 1999, 121, 10640.
91. [31c] N. Etkin, T. L. Dzwiniel, K. E. Schweibert, J. M. Stryker, J. Am. Chem. Soc. 1998, 120, 9702.
92. [31d] Z. L. Lutsenko, P. V. Petrovski, A. A. Bezrukova, A. Z. Rubezhov, Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 4, 855.
93. T. Nishikawa, H. Shinokubo, K. Oshima, Org. Lett. 2002, 4, 2795.
94. Y. Hayashi, H. Shinokubo, K. Oshima, Tetrahedron Lett. 1998, 39, 63.
95. [34a] M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978.
96. [34b] M. Nakamura, K. Matsuo, T. Inoue, E. Nakamura, Org. Lett. 2003, 5, 1373.
97. M. Hojo, Y. Murakami, H. Aihara, R. Sakuragi, Y. Baba, A. Hosomi, Angew. Chem. Int. Ed. 2001, 40, 621.
98. [36a] M. Tamura, J. K. Kochi, J. Am. Chem. Soc. 1971, 93, 1487.
99. [36b] M. Tamura, J. K. Kochi, Synthesis 1971, 303.
100. [36c] S. M. Neumann, J. K. Kochi, J. Org. Chem. 1975, 40, 599.
101. [36d] R. S. Smith, J. K. Kochi, J. Org. Chem. 1976, 41, 502.
102. [36e] J. K. Kochi, Acc. Chem. Res. 1974, 7, 351.
103. G. Cahiez, H. Avedissian, Synthesis 1998, 1199.
104. [38a] A. Fürstner, A. Leitner, Angew. Chem. Int. Ed. 2002, 41, 609.
105. [38b] A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856.
106. A. Fürstner, A. Leitner, Angew. Chem. Int. Ed. 2003, 42, 308.
107. A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. Int. Ed. 2003, 42, 5358.
108. Y. Nishii, K. Wakasugi, Y. Tanabe, Synlett 1998, 67.
109. [42a] A. Yanagisawa, N. Nomura, H. Yamamoto, Tetrahedron 1994, 50, 6017.
110. [42b] A. Yanagisawa, N. Nomura, H. Yamamoto, Synlett 1991, 513.
111. A. Fürstner, M. Méndez, Angew. Chem. Int. Ed. 2003, 42, 5355.
112. T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386.
113. K. Wakabayashi, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2001, 123, 5374.
114. T. Fujioka, T. Nakamura, H. Yorimitsu, K. Oshima, Org. Lett. 2002, 4, 2257.
115. Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2002, 124, 6514.
116. K. Mizutani, H. Shinokubo, K. Oshima, Org. Lett. 2003, 5, 3959.
117. T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed. 2002, 41, 4137.