Design of catalytic processes based on studies of elementary processes

Journal of Organometallic Chemistry

Volumn 689, Issue 24 SPEC. ISS., 2004, Pages 4499-4510

  Yamamoto, Akio ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

Aldehyde synthesis; Elementary processes; Ketone synthesis; Pd catalyzed organic syntheses; Transition metal alkyls

Indexed keywords

ALDEHYDES; CARBOXYLIC ACIDS; CATALYSIS; CHEMICAL BONDS; KETONES; OLEFINS;

CATALYTIC PROCESSES; ORGANOMETALLIC CHEMISTRY;

ORGANOMETALLICS;

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; KETONE; PERFLUORO COMPOUND;

BENZYLATION; CATALYSIS; CHEMICAL BOND; ORGANIC CHEMISTRY; REVIEW; SYNTHESIS;

EID: 9944257411     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.05.055     Document Type: Article

References (105)

1. A. Yamamoto J. Organomet. Chem. 473 1994 11 27
2. A. Yamamoto J. Organomet. Chem. 653 2002 5
3. A. Yamamoto J. Chem. Soc., Dalton Trans. 1997 1027
4. A. Yamamoto J. Organomet. Chem. 300 1986 347
5. A. Yamamoto J. Organomet. Chem. 600 2000 159
6. K. Ziegler, E. Holtzkamp, H. Breil, and H. Martin Angew. Chem. 67 1955
7. G. Fink R. Mullhaupt H.H. Brintzinger Ziegler Catalysis 1995 Springer Berlin, Heidelberg
8. G. Natta, and F. Danusso Stereoregular Polymers and Stereospecific Polymerizations vols. 1-2 1967 Pergamon Oxford
9. G. Wilke J. Organometal. Chem. 200 1980 349
10. P. Cossee J. Catal. 3 1964 80
11. F.A. Cotton Chem. Rev. 55 1955 551
12. A. Yamamoto, K. Morifuji, S. Ikeda, T. Saito, Y. Uchida, and A. Misono J. Am. Chem. Soc. 87 1965 4652
13. T. Saito, Y. Uchida, A. Misono, A. Yamamoto, K. Morifuji, and S. Ikeda J. Am. Chem. Soc. 88 1966 198
14. A. Yamamoto, K. Morifuji, S. Ikeda, T. Saito, Y. Uchida, and A. Misono J. Am. Chem. Soc. 87 1965 4652
15. A. Yamamoto, K. Morifuji, S. Ikeda, T. Saito, Y. Uchida, and A. Misono J. Am. Chem. Soc. 90 1968 1878
16. A. Yamamoto, and S. Ikeda J. Am. Chem. Soc. 89 1967 5989
17. T. Yamamoto, A. Yamamoto, and S. Ikeda J. Am. Chem. Soc. 93 1971 3350
18. T. Yamamoto, A. Yamamoto, and S. Ikeda J. Am. Chem. Soc. 93 1971 3360
19. L. Vaska Ace. Chem. Res. 1 1968
20. J.P. Collman, and W.R. Roper Adv. Organometal. Chem. 7 1968
21. J. Halpern Ace. Chem. Res. 3 1970
22. H. Sinn, W. Kaminsky, H.-J. Vollmer, and R. Woldt Angew. Chem. Int. Ed. Engl. 19 1980 390
23. W. Kaminsky, and M. Arndt B. Cornils W.A. Herrmann Applied Homogeneous Catalysis with Organometallic Compounds vol. 1 1996 VCH Weinheim
24. W. Kaminsky Metalorganic Catalysts for Synthesis and Polymerization 1999 Springer Berlin
25. H.H. Brintzinger, D. Fischer, R. Muhlhaupt, B. Rieger, and R. Waymouth Angew. Chem 107 1995 1255
26. C.M. Killian, D.J. Tempel, L.K. Johnson, and M. Brookhart J. Am. Chem. Soc. 118 1996 11664
27. G.J.P. Britovsek, V.C. Gibson, B.S. Kimberley, P.J. Maddox, S.J. McTavish, G.A. Solan, A.J.P. White, and D.J. Williams Chem. Commun. 1998 845
28. We did examine the effects of addition of Lewis acids in enhancing the reactivity of the isolated transition metal alkyls without knowing the effect of MAO T. Yamamoto, and A. Yamamoto J. Organomet. Chem. 57 1973 127
29. A. Yamamoto J. Organometal. Chem. 500 1995 337
30. Y. Kayaki, I. Shimizu, and A. Yamamoto Chem. Lett. 1995 1089
31. Y. Kayaki, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 70 1997 917
32. A. Yamamoto, Y. Kayaki, K. Nagayama, and I. Shimizu Synlett 2000 925
33. 3) have been addressed by two groups after 30 years (!) since our first publication F. Schaper, S.R. Foley, and R.F. Jordan J. Am. Chem. Soc. 126 2004 2114
34. P.J. Bryan, C.K. Chan, and M.C. Baird Organometallics 23 2004 2752
35. A. Yamamoto, S. Kitazume, L.S. Pu, and S. Ikeda Chem. Commun. 1967 79
36. A. Yamamoto, S. Kitazume, L.S. Pu, and S. Ikeda J. Am. Chem. Soc. 93 1971 371
37. T. Ito, S. Kitazume, A. Yamamoto, and S. Ikeda J. Am. Chem. Soc 92 1970
38. A. Yamamoto, M. Ookawa, and S. Ikeda Chem. Commun. 1969 841
39. A. Yamamoto, S. Go, M. Ookawa, M. Takahashi, S. Ikeda, and T. Keii Bull. Chem. Soc. Jpn. 45 1972 3110
40. Y. Miura, and A. Yamamoto Chem. Lett. 1978 937
41. A. Yamamoto, Y. Miura, T. Ito, H.-L. Chen, K. Iri, F. Ozawa, K. Miki, T. Sei, N. Tanaka, and N. Kasai Organometallics 2 1983 1429
42. M. Uchino, A. Yamamoto, and S. Ikeda J. Organomet. Chem. 24 1970
43. M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda J. Organomet. Chem. 84 1975 93
44. K. Tamao, K. Sumitani, and M. Kumada J. Am. Chem. Soc. 94 1972
45. K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada Bull. Chem. Soc. Jpn 49 1976 1958
46. R.J.P. Corriu, and J.P. Masse J. Chem. Soc. Chem. Commun. 1972 144
47. F. Diedrich P.J. Stang Metal-catalyzed Cross-coupling Reactions 1998 Wiley-VCH Weinheim
48. T. Yamamoto, and A. Yamamoto Chem. Lett. 1977 353
49. K. Mori, T. Mizoroki, and A. Ozaki Bull. Chem. Soc. Jpn. 46 1973 1505
50. H.A. Dieck, and R.F. Heck J. Am. Chem. Soc. 96 1974 1133
51. J. Tsuji Organic Syntheses with Palladium Compounds 1980 Springer Berlin
52. B.M. Trost Ace. Chem. Res 13 1980 385
53. F. Ozawa, and A. Yamamoto Chem. Lett. 1982 865
54. F. Ozawa, H. Soyama, T. Yamamoto, and A. Yamamoto Tetrahedron Lett. 23 1982
55. A. Yamamoto, T. Yamamoto, S. Komiya, and F. Ozawa Pure Appl. Chem. 56 1984
56. F. Ozawa, N. Kawasaki, T. Yamamoto, and A. Yamamoto Chem. Lett. 1985 567
57. F. Ozawa, H. Soyama, H. Yanagihara, I. Aoyama, H. Takino, K. Izawa, T. Yamamoto, and A. Yamamoto J. Am. Chem. Soc. 107 1985
58. F. Ozawa, T. Ito, Y. Nakamura, and A. Yamamoto Bull. Chem. Soc. Jpn. 54 1981 1868
59. K, Tatsumi, R. Hoffmann, A. Yamamoto, and J.K. Stille Bull. Chem. Soc. Jpn. 54 1981 1857
60. F. Ozawa, T. Ito, and A. Yamamoto J. Am. Chem. Soc. 102 1980 6457
61. K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto J. Am. Chem. Soc. 106 1984 8181
62. F. Ozawa, and A. Yamamoto Chem. Lett. 1981 289
63. A. Yamamoto, T. Yamamoto, S. Komiya, and F. Ozawa Pure Appl. Chem. 56 1984 1621
64. A. Yamamoto, F. Ozawa, K. Osakada, L. Huang, T.-I. Son, N. Kawasaki, and M.-K. Doh Pure Appl. Chem. 63 1991 687
65. A. Yamamoto Bull. Chem. Soc. Jpn. 68 1995 433
66. F. Ozawa, N. Kawasaki, H. Okamoto, T. Yamamoto, and A. Yamamoto Organometallics 6 1987
67. F. Ozawa, H. Soyama, H. Yanagihara, I. Aoyama, H. Takmo, K. Izawa, T. Yamamoto, and A. Yamamoto J. Am. Chem. Soc. 107 1985 3235
68. A. Yamamoto Adv. Organometal. Chem. 34 1991 111
69. Y.-S. Lin, A. Yamamoto, in: S. Murai Ed, Topics in Organometallic Chemistry, vol. 3, p. 162
70. For earlier example, see T. Yamamoto, J. Ishizu, and A. Yamamoto Chem. Lett. 1979 991
71. T. Yamamoto, J. Ishizu, and A. Yamamoto Chem. Lett. 1979 1385
72. T. Kohara, S. Komiya, T. Yamamoto, and A. Yamamoto Chem. Lett. 1979 1513
73. T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto J. Am. Chem. Soc. 102 1980
74. S. Komiya, A. Yamamoto, and T. Yamamoto Chem. Lett. 1981 193
75. T. Yamamoto, O. Saito, and A. Yamamoto J. Am. Chem. Soc. 103 1981 5600
76. T. Yamamoto, J. Ishizu, and A. Yamamoto J. Am. Chem. Soc. 103 1981 6863
77. T. Yamamoto, J. Ishizo, and A. Yamamoto Bull. Chem. Soc. Jpn. 55 1982 623
78. For reviews of the development of catalytic processes involving the cleavage of the C-O bond to organic synthesis, see: A. Yamamoto, V. Kayaki, K. Nagayama, and I. Shimizu Synlett 2000 925
79. A. Yamamoto, R. Kakino, and I. Shimizu Helv. Chim. Acta 84 2001 2996
80. A. Yamamoto Pure and Appl. Chem. 74 2002 1
81. H. Hey, and H.-J. Arpe Angew. Chem. Int. Ed. Engl. 12 1973 928
82. J. Tsuji, and T. Yamakawa Tetrahedron Lett. 7 1979 613
83. J. Tsuji, I. Minami, and I. Shimizu Synthesis 623 1986
84. M. Oshima, I. Shimizu, A. Yamamoto, and F. Ozawa Organometallics 10 1991
85. M. Oshima, T. Sakamoto, Y. Maruyama, F. Ozawa, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 73 2000 453
86. A. Yamamoto Bull. Chem. Soc. Jpn. 68 1995 433
87. T. Terashima, I. Shimizu, A. Yamamoto, unpublished results
88. K. Nagayama, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 72 1999 799
89. K. Narahashi, A. Yamamoto, and I. Shimizu Chem. Lett. 33 2004 348
90. K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu, and A. Yamamoto Chem. Lett. 1995 367
91. K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 72 1999 573
92. K. Nagayama, I. Shimizu, and A. Yamamoto Chem. Lett. 1143 1998
93. K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 72 1999 799
94. K. Nagayama, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn 74 2001 1803
95. L.J. Gooßen, and K. Ghosh Chem. Commun. 2002 836
96. L.J. Gooßen, and K. Ghosh Chem. Commun. 2084 2001
97. H. Munakata, A. Miyamoto, A. Yamamoto, K. Nagayama, presented at the 86th Annual Meeting of Catalysis Society of Japan, September 21, 2000, Tottori, Japan
98. A. Suzuki Ace. Chem. Res. 15 1982 178
99. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
100. R. Kakino, H. Narahashi, I. Shimizu, and A. Yamamoto Chem. Lett. 2001 1242
101. R. Kakino, S. Yasumi, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 75 2002 137
102. R. Kakino, I. Shimizu, and A. Yamamoto Chem. Lett. 2001 1242
103. R. Kakino, H. Narahashi, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 75 2002 1333
104. L.J. Gooßen, and K. Ghosh Angew. Chem. Int. 40 2001 3458
105. L.J. Gooßen, and K. Ghosh Chem. Commun. 2001 2084