Heterogeneous Catalysis

Modern Organonickel Chemistry

Volumn , Issue , 2005, Pages 273-305

  Osawa, Tsutomu ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Asymmetric syntheses; Catalytic reactions; Heterogeneous catalysis; Heterogeneous nickel catalysts; Modification of base nickel catalyst; Nickel boride; Organonickel chemistry; Preparation of base nickel catalyst; Raney nickel; Tartaric acid modified nickel catalyst

Indexed keywords

EID: 83155188667     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527604847.ch10     Document Type: Chapter

References (133)

1. P. Sabatier, J. B. Senderens, Compt. Rend. 1897, 124, 1359.
2. H. U. Blaser, Reactions at Surfaces: Opportunities and Pitfalls for the Organic Chemist; Modern Synthetic Methods 7, Ed. B. Ernst, Ch. Leumann, John Wiley & Sons Inc., 1995, p. 179.
3. R. L. Augustine, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Dekker, 1996.
4. M. Garland, H. P. Jalett, H. U. Blaser, Stud. Surf. Sci. Catal. 1991, 59, 177.
5. J. R. Rostrup-Nielsen, Catalysis Science and Technology, 5, Eds. J. R. Anderson, M. Boudart, Springer, Berlin, 1984, p. 3 and references therein.
6. T. Numaguchi, Catal. Surv. Jpn. 2001, 5, 59 and references therein.
7. D. D. Whitehurst, T. Isoda, I. Mochida, Adv. Catal. 1998, 42, 345 and references therein.
8. C. Song, Catal. Today 2003, 86, 211 and references therein.
9. Y. Saih, K. Segawa, Catal. Surv. Asia 2003, 7, 235 and references therein.
10. S. Takenaka, T. Shimizu, K. Otsuka, Int. J. Hydrogen Energy 2004, 29, 1065.
11. "The Catalytic Reaction Guide" available from Johnson Matthey.
12. "Chemical Reactions Promoted by Engelhard Catalysts" available from Engelhard.
13. Hydrogenation with Raney Catalysts, Kawaken Fine Chemical Co. Ltd., 1980.
14. H. U. Blaser, U. Siegrist, H. Steiner, M. Studer, Fine Chemicals through Heterogeneous Catalysis, Eds. R. A. Sheldon, H. van Bekkum, Wiley-VHC, 2001, p. 389.
15. R. A. Sheldon, H. van Bekkum, Eds. Fine Chemicals through Heterogeneous Catalysis, Wiley-VHC, 2001.
16. G. V. Smith, F. Notheisz, Heterogeneous Catalysis in Organic Chemistry, Academic Press, 1999.
17. S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, John Wiley & Sons, Inc., 2001.
18. M. Paul, Bull. Soc. Chim. Fr. 1940, 7, 196.
19. E. Lieber, F. L. Morritz, Adv. Catal. 1953, 4, 417.
20. H. Pines, Adv. Catal. 1987, 35, 323.
21. A. Abbadi, H. Van Bekkum, Fine Chemicals through Heterogeneous Catalysis, Eds. R. A. Sheldon, H. van Bekkum, Wiley-VHC, 2001, p. 380.
22. L. W. Covert, H. Adkins, J. Am. Chem. Soc. 1932, 54, 4116
23. R. Mozingo, Org. Syn. 1941, 21, 15
24. A. A. Pavlic, H. Adkins, J. Am. Chem. Soc. 1946, 68, 1471
25. H. Adkins, H. R. Billica, J. Am. Chem. Soc. 1948, 70, 695
26. N. A. Khan, J. Am. Chem. Soc. 1952, 74, 3018.
27. J. Freel, W. J. M. Pieters, R. B. Anderson, J. Catal. 1970, 16, 281 and references therein.
28. R. Richards, G. Geibel, W. Hofstadt, H. Bonnemann, Appl. Organometal. Chem. 2002, 16, 377 and references therein.
29. F. Devred, B. W. Hoffer, W. G. Sloof, P. J. Kooyman, A. D. van Langeveld, H. W. Zandbergen, Appl. Catal. A: Gen. 2003, 244, 291.
30. H. Lei, Z. Song, D. Tan, X. Bao, X. Mu, B. Zong, E. Min, Appl. Catal. A: Gen. 2001, 214, 69.
31. B. Liu, M. Qiao, J. F. Deng, K. Fan, X. Zhang, B. Zong, J. Catal. 2001, 204, 512.
32. B. Volk, T. Mezei, G. Simig, Synthesis 2002, 595.
33. R. Paul, P. Buisson, N. Joseph, Ind. Eng. Chem. 1952, 44, 1006.
34. C. A. Brown, V. K. Ahuja, J. Org. Chem. 1973, 38, 2226 and references therein.
35. Reference [3] p. 367.
36. A. Molnar, G. V. Smith, M. Bartok, Adv. Catal. 1987, 36, 329 and references therein.
37. J. F. Deng, H. Li, W. Wang, Catal. Today 1999, 51, 113 and references therein.
38. H. Li, H. Li, W. Dai, M. Qiao, Appl. Catal. A: Gen. 2003, 238, 119 and references therein.
39. Y. Okamoto, Y. Nitta, T. Imanaka, S. Teranishi, J. Chem. Soc. Faraday Tans. I 1979, 75, 2027.
40. H. Li, H. Li, W. L. Dai, W. Wang, Z. Fang, J. F. Deng, Appl. Surf. Sci. 1999, 152, 25.
41. H. Li, H. Li, W. L. Dai, J. F. Deng, Appl. Catal. A: Gen. 2001, 207, 151 and references therein.
42. R. Zhang, F. Li, N. Zhang, Q. Shi, Appl. Catal. A: Gen. 2003, 239, 17 and references therein.
43. J. W. Geus, J. A. R. van Veen, Stud. Sur. Sci. Catal. 1999, 123, 459.
44. M. Campanati, G. Fornasari, A. Vaccari, Catal. Today 2003, 77, 299 and references therein.
45. K. Tohji, Y. Udagawa, S. Tanabe, A. Ueno, J. Am. Chem. Soc. 1984, 106, 612.
46. Y. Ueno, H. Suzuki, Y. Kotera, J. Chem. Soc., Faraday Trans. 1, 1983, 79, 127.
47. P. H. Courty, H. Ajot, C. H. Marcilly, B. Delmon, Powder Technology 1973, 7, 21.
48. R. Takahashi, S. Sato, T. Sodesawa, M. Suzuki, N. Ichikuni, Micropor. Mesopor. Mater. 2003, 66, 197 and references therein.
49. S. Sato, R. Takahashi, T. Sodesawa, F. Nozaki, X. Z. Jin, S. Suzuki, T. Nakayama, J. Catal. 2000, 191, 261.
50. B. H. Lipshutz, S. Tasler, W. Chrisman, B. Spliethoff, B. Tesche, J. Org. Chem. 2003, 68, 1177 and references therein.
51. S. Iyer, V. V. Thakur, J. Mol. Catal. A: Chem. 2000, 157, 275.
52. A. Baiker, J. Mol. Catal. A: Chem. 1997, 115, 473.
53. A. Tungler, T. Tarnai, T. Máthé, J. Petró, R. A. Sheldon, Chiral Reactions in Heterogeneous Catalysis, Eds. G. Jannes, V. Duboi, Plenum Press, 1995, p. 121.
54. M. Besson, C. Pinel, Topics in Catal. 1998, 5, 25.
55. P. Kukula, R. Prins, Topics in Catal. 2003, 25, 29 and references therein.
56. D. E. De Vos, M. De bruyn, V. I. Parvulescu, F. G. Cocu, P. A. Jacobs, Chiral Catalyst Immobilization and Recycling, Eds. D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs, Wiley-VCH, 2000, p. 283.
57. J. M. Brown, Angew. Chem. Int. Ed. Engl. 1987, 26, 190.
58. L. Horner, H. Ziegler, H. D. Ruprecht, Liebigs Ann. Chem. 1979, 341.
59. G. Knupp, A. W. Frahm, Arch. Pharm. (Weinheim) 1985, 318, 250.
60. A. Gypser, H. D. Scharf, Synthesis 1996, 349.
61. M. A. Huffman, P. J. Reider, Tetrahedron Lett. 1999, 40, 831.
62. J. R. Del Valle, M. Goodman, J. Org. Chem. 2003, 68, 3923.
63. G. M. Schwab, L. Rudolph, Naturwissenschaften 1932, 20, 362.
64. T. D. Stewart, D. Lipkin, J. Am. Chem. Soc. 1939, 61, 3297.
65. Y. Izumi, M. Imaida, H. Fukawa, S. Akabori, Bull. Chem. Soc. Jpn. 1963, 36, 155.
66. K. Molvinger, M. Lopez, J. Court, Tetrahedron: Asymmetry 2000, 11, 2263.
67. K. Molvinger, J. Court, H. Jobic, J. Mol. Catal. A: Chem. 2001, 174, 245.
68. Y. Izumi, Angew. Chem., Int. Ed. Engl. 1971, 10, 871.
69. M. J. Fish, D. F. Ollis, Catal. Rev. Sci. Eng. 1978, 18, 259.
70. Y. Izumi, Adv. Catal. 1983, 32, 215.
71. A. Tai, T. Harada, Tailored Metal Catalysts, Ed. Y. Iwasawa, Reidel, Dordrecht, 1986, p. 265 and references therein.
72. E. I. Klabunovskii, Russian Chem. Rev. 1991, 60, 980.
73. G. Webb, P. B. Wells, Catalysis Today 1992, 12, 319.
74. T. Osawa, T. Harada, A. Tai, Catalysis Today 1997, 37, 465 and references therein.
75. T. Sugimura, Catalysis Surveys from Japan 1999, 3, 37.
76. T. Osawa, T. Harada, O. Takayasu, Topics in Catalysis 2000, 13, 155.
77. A. Tai, T. Sugimura, Chiral Catalyst Immobilization and Recycling, Eds. D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs, Wiley-VCH, 2000, p. 173.
78. Y. Izumi, M. Imaida, H. Fukawa, S. Akbori, Bull. Chem. Soc. Jpn. 1963, 36, 21.
79. Y. Izumi, S. Tatsumi, M. Imaida, Y. Fukuda, S. Akbori, Bull. Chem. Soc. Jpn. 1966, 39, 361.
80. T. Harada, S. Onaka, A. Tai, Y. Izumi, Chem. Lett. 1977, 1131.
81. T. Harada, Y. Izumi, Chem. Lett. 1978, 1195.
82. T. Harada, Y. Sasaki, T. Kitamura, H. Hatta, K. Niwa, T. Osawa, A. Tai, Abstract for the 8th International Symposium on Relations between Homogeneous and Heterogeneous Catalysis, Balatonfüred 1995, P78.
83. T. Osawa, T. Harada. A. Tai, O. Takayasu, I. Matsuura, Stud. Surf. Sci. Catal. 1997, 108, 199.
84. T. Harada, M. Yamamoto, S. Onaka, M. Imaida, H. Ozaki, A. Tai, Y. Izumi, Bull. Chem. Soc. Jpn. 1981, 54, 2323.
85. J. Masson, P. Cividino, J. Court, J. Mol. Catal., A: Chem. 1996, 111, 289.
86. T. Harada, Y. Imachi, A. Tai, Y. Izumi, Metal-Support and Metaladditive Effects in Catalysis, Lyon 1982, 377.
87. H. Brunner, M. Muschiol, T. Wischert, Tetrahedron: Asymmetry 1990, 1, 159.
88. T. Osawa, E. Mieno, T. Harada, O. Takayasu, J. Mol. Catal. A: Chem. 2003, 200, 315.
89. T. Osawa, Y. Amaya, T. Harada, O. Takayasu, J. Mol. Catal. A: Chem. 2004, 211, 93.
90. Y. Nitta, F. Sekine, T. Imanaka, S. Teranishi, J. Catal. 1982, 74, 382.
91. A. Hoek, W. M. H. Sachtler, J. Catal. 1979, 58, 276.
92. Y. Nitta, F. Sekine, T. Imanaka, S. Teranishi, Bull. Chem. Soc. Jpn. 1981, 54, 980.
93. A. Wolfson, S. Geresh, M. V. Landau, M. Herskowitz, Appl. Catal. A: Gen. 2001, 208, 91.
94. T. Osawa, A. Tai, Y. Imachi, S. Takasaki, Chiral Reactions in Heterogeneous Catalysis, Eds. G. Jannes, V. Dubois, Plenum Press, 1995, p. 75.
95. S. Kasyu, M. Nagase, C. Hayashi, R. Uyeda, N. Wada, T. Tasaki, Proceedings of 6th International Vacuum Congress 1974, 491.
96. L. J. Bostelaar, W. M. H. Sachtler, J. Mol. Catal. 1984, 27, 377.
97. P. Kukula, L. Cerveny, Appl. Catal. A: Gen. 2001, 210, 237.
98. E. Leclercq, A. Rives, E. Payen, R. Hubaut, Appl. Catal. A: Gen. 1998, 168, 279.
99. T. Osawa, Y. Hayashi, A. Ozawa, T. Harada, O. Takayasu, J. Mol. Catal. A: Chem. 2001, 169, 289.
100. M. A. Keane, Langmuir, 1997, 13, 41 and references therein.
101. T. Osawa, S. Sakai, K. Deguchi, T. Harada, O. Takayasu, J. Mol. Catal. A: Chem. 2002, 185, 65.
102. S. Sugimura, T. Osawa, S. Nakagawa, T. Harada, A. Tai, Stud. Sur. Sci. Catal. 1996, 101, 231.
103. S. Nakagawa, T. Sugimura, A. Tai, Chem. Lett. 1997, 859.
104. S. Nakagawa, A. Tai, T, Okuyama, T. Sugimura, Topics in Catalysis 2000, 13, 187.
105. A. Tai, T. Harada, Y. Hiraki, S. Murakami, Bull. Chem. Soc. Jpn. 1983, 56, 1414.
106. Y. Hikaki, K. Ito, T. Harada, A. Tai, Chem. Lett. 1981, 131.
107. S. Murakami, T. Harada, A. Tai, Bull. Chem. Soc. Jpn. 1980, 53, 1356.
108. Y. Orito, S. Niwa, S. Imai, Yukigouseikagaku 1976, 34, 34.
109. A. Tai, K. Tsukioka, Y. Imachi, Y. Inoue, H. Ozaki, T. Harada, Y. Izumi, Proc. 8th Intr. Congr. Catal., Berlin (West) 1984, V-531.
110. A. Tai, K. Tsukioka, H. Ozaki, T. Harada, Y. Izumi, Chem. Lett. 1984, 2083.
111. T. Osawa, T. Harada, Bull. Chem. Soc. Jpn. 1984, 57, 1518.
112. T. Osawa, Chem. Lett. 1985, 1609.
113. T. Osawa, T. Harada, and A. Tai, Abstracts for the 7th International Symposium on Relations Between Homogeneous and Heterogeneous Catalysis, Tokyo 1992, 230.
114. T. Harada, T. Osawa, Chiral Reactions in Heterogeneous Catalysis, Eds. G. Jannes, V. Dubois, Plenum Press, 1995, p. 83.
115. T. Osawa, N. Ozaki, T. Harada, O. Takayasu, Bull. Chem. Soc. Jpn. 2002, 75, 2695.
116. T. Osawa, K. Sawada, T. Harada, O. Takayasu, Appl. Catal. A: Gen. 2004, 264, 33.
117. A. López-Martínez, M. A. Keane, J. Mol. Catal. A; Chem. 2000, 153, 257.
118. T. Tanabe, K. Okuda, and Y. Izumi, Bull. Chem. Soc. Jpn. 1973, 46, 514.
119. T. Harada, A. Tai, M. Yamamoto, H. Ozaki, Y. Izumi, Proc. 7th Int. Cong. Catal. 1981, 364.
120. D. R. Bichards, H. H. Kung, W. M. H. Sachtler, J. Mol. Catal. 1986, 36, 329.
121. Y. Inoue, K. Okabe, I. Yasumori, Bull. Chem. Soc. Jpn. 1981, 54, 613.
122. Y. Sakata, K. Domen, K. Maruya, T. Onishi, Catal. Lett. 1990, 4, 169.
123. P. Kukula, L. Cerveny, Appl. Catal. A: Gen. 2002, 223, 43.
124. V. Humblot, S. Haq, C. Muryn, W. A. Hofer, R. Raval, J. Am, Chem, Soc. 2002, 124, 503.
125. T. E. Jones, X. J. Baddeley, Surface Science 2002, 513, 453.
126. H. Ozaki, A. Tai, S. Kobatake, H. Watanabe, Y. Izumi, Bull. Chem. Soc. Jpn. 1978, 51, 3559.
127. I. Yasumori, M. Yokozeki, Y. Inoue, Faraday Discuss. Chem. Soc. 1982, 72, 385.
128. H. M. Woerde, L. J. Bostelaar, A. Hoek, W. M. H. Sachtler, J. Catal. 1982, 76, 316.
129. Y. Nitta, T. Imanaka, S. Teranishi, J. Catal. 1983, 80, 31.
130. W. M. H. Sachtler, Chem. Ind. (Dekker) 1985, 22, 189.
131. M. A. Keane, J. Chem. Soc., Faraday Trans. 1997, 93, 201.
132. K. A. Keane, G. Webb, J. Chem. Soc., Chem. Commun. 1991, 1619.
133. T. E. Jones, C. J. Baddeley, Surface Science 2002, 519, 237.