Homogeneous Hydrogenation of Carbon Dioxide

Chemical Reviews

Volumn 95, Issue 2, 1995, Pages 259-272

  Jessop, Philip G ^a   Ikariya, Takao ^a   Noyori, Ryoji ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001458108     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr00034a001     Document Type: Article

References (132)

1. Aresta, M. In Enzymatic and Model Carboxylation and Reduction Reactions for Carbon Dioxide Utilization; Aresta, M., Schloss, J. V., Eds.; NATO ASI Series. Series C.; Kluwer Academic: Dordrecht, 1990; Vol. 314, pp 1-18.
2. Ford, P. C. In Electrochemical and Electrocatalytic Reactions of Carbon Dioxide; Sullivan, B. P., Krist, K., Guard, H. E., Eds.; Elsevier: Amsterdam, 1993; Chapter 3, pp 68-93.
3. Koinuma, H.; Kawakami, F.; Kato, H.; Hirai, H. J. Chem. Soc., Chem. Commun. 1981, 213-214.
4. Eisenschmid, T. C.; Eisenberg, R. Organometallics 1989, 8, 1822-1824.
5. Suss-Fink, G.; Reiner, J. J. Organomet. Chem. 1981,221, C36-C38.
6. Electrochemical and Electrocatalytic Reactions of Carbon Dioxide; Sullivan, B. P., Krist, K., Guard, H. E., Eds.; Elsevier: Amsterdam, 1993.
7. Kolomnikov, I. S.; Lysyak, T. V. Russ. Chem. Rev. 1990, 59, 344-360.
8. Ziessel, R. In Carbon Dioxide as a Source of Carbon; Aresta, M., Forti, G., Eds.; D. Reidel: Dordrecht, 1987; pp 113-138.
9. Ziessel, R. Nouv. J. Chim. 1983, 7, 613-633.
10. Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747-764.
11. Eisenberg, R.; Hendriksen, D. E. Adv. Catal. 1979,28, 79-172.
12. Behr, A. Carbon Dioxide Activation by Metal Complexes; VCH: Weinheim, 1988.
13. Haggin, J. Chem. Eng. News 1994, 72 (13), 29-31.
14. Creutz, C. In Electrochemical and Electrocatalytic Reactions of Carbon Dioxide; Sullivan, B. P., Krist, K., Guard, H. E., Eds.; Elsevier: Amsterdam, 1993; Chapter 2, pp 19-67.
15. Darensbourg, D. J. In Enzymatic and Model Carboxylation and Reduction Reactions for Carbon Dioxide Utilization; Aresta, M., Schloss, J. V., Eds.; NATO ASI Series, Series C.; Kluwer Academic: Dordrecht, 1990; Vol. 314, pp 43-64.
16. Darensbourg, D. J.; Bauch, C. G.; Ovalles, C. In Catalytic Activation of Carbon Dioxide; Ayers, W. M., Ed.; ACS Symposium Series 363; American Chemical Society: Washington, DC, 1988; Chapter 4, pp 26-41.
17. Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661-678.
18. Walther, D. Coord. Chem. Rev. 1987, 79, 135-174.
19. Inoue, S.; Koinuma, H. Rev. Inorg. Chem. 1984, 6, 291-355.
20. Palmer, D. A.; Van Eldik, R. Chem. Rev. 1983, 83, 651-731.
21. Behr, A. In Catalysis in C1 Chemistry, Keim, W., Ed.; D. Reidel: Dordrecht, 1983; pp 169-217.
22. Darensbourg, D. J.; Kudaroski, R. A. Adv. Organomet. Chem. 1983,22, 129-168.
23. Sneeden, R. P. A. In Comprehensive Organometallic Chemistry, Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 225-283.
24. Ito, T.; Yamamoto, A. In Organic and Bio-organic Chemistry of Carbon Dioxide; Inoue, S., Yamazaki, N., Eds.; Kodansha: Tokyo, 1982; Chapter 3, pp 79-151.
25. Vol'pin, M. E.; Kolomnikov, I. S. Pure Appl. Chem. 1973, 33, 567-581.
26. Calabrese, J. C.; Herskovitz, T.; Kinney, J. B. J. Am. Chem. Soc. 1983, 105, 5914-5915.
27. Gambarotta, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Am. Chem. Soc. 1985, 107, 2985-2986.
28. Aresta, M.; Nobile, C. F.; Albano, V. G.; Fomi, E.; Manassero, M. J. Chem. Soc., Chem. Commun. 1975, 636-637.
29. Pinkes, J. R.; Steffey, B. D.; Vites, J. C.; Cutler, A. R. Organometallics 1994, 13, 21-23.
30. Fujita, E.; Creutz, C.; Sutin, N.; Brunschwig, B. S. Inorg. Chem. 1993, 32, 2657-2662.
31. Komiya, S.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1976,49, 784-787.
32. Bradley, M. G.; Roberts, D. A.; Geoffroy, G. L. J. Am. Chem. Soc. 1981, 103, 379-384.
33. Merrifield, J. H.; Gladysz, J. A. Organometallics 1983, 2, 782-784.
34. Bo, C.; Dedieu, A. Inorg. Chem. 1989, 28, 304-309.
35. Kolomnikov, I. S.; Stepovska, G.; Tyrlik, S.; Vol'pin, M. E. J. Gen. Chem. USSR, 1972, 42, 1645.
36. Grice, N.; Kao, S. C.; Pettit, R. J. Am. Chem. Soc. 1979, 101, 1627-1628.
37. Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941-3942.
38. King, R. B.; Frazier, C. C.; Hanes, R. M.; King, A. D., Jr. J. Am. Chem. Soc. 1978, 100, 2925-2927.
39. Cheng, C.-H.; Hendriksen, D. E.; Eisenberg, R. J. Am. Chem. Soc. 1977, 99, 2791-2792.
40. Darensbourg, D. J.; Rokicki, A. Organometallics 1982,1, 1685-1693.
41. Sakaki, S.; Ohkubo, K. Inorg. Chem. 1989, 28, 2583-2590.
42. Chisholm, M. H.; Cotton, F. A.; Extine, M. W.; Reichert, W. W. J. Am. Chem. Soc. 1978, 100, 1727-1734.
43. Chisholm, M. H.; Cotton, F. A.; Extine, M. W.; Stults, B. R. Inorg. Chem. 1977, 16, 603-611.
44. Chisholm, M. H.; Extine, M. W. J. Am. Chem. Soc. 1977, 99, 792-802.
45. CRC Handbook of Chemistry and Physics, 63rd ed.; Weast, R. C., Astle, M. J., Eds.; CRC: Boca Raton, FL, 1982.
46. Lange's Handbook of Chemistry, 11th ed.; Dean, J. A., Ed.; McGraw-Hill, Inc.: New York, 1973.
47. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: London, 1986.
48. Reid, E. B. In McGraw-Hill Encyclopedia of Science & Technology, 5th ed.; McGraw-Hill Book: New York, 1982; Vol. 5, p 670.
49. Reutemann, W.; Kieczka, H. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Ravenscroft, M., Rounsaville, J. F., Schulz, G., Eds.; VCH: Weinheim, 1989; Vol. A12, pp 13-33.
50. Farlow, M. W.; Adkins, H. J. Am. Chem. Soc. 1935, 57, 2222-2223.
51. Inoue, Y.; Izumida, H.; Sasaki, Y.; Hashimoto, H. Chem. Lett. 1976, 863-864.
52. Graf, E.; Leitner, W. J. Chem. Soc., Chem. Commun. 1992, 623-624.
53. Leitner, W.; Dinjus, E.; Gassner, F. J. Organomet. Chem. 1994, 475, 257-266.
54. Kudo, K.; Phala, H.; Sugita, N.; Takezaki, Y. Chem. Lett. 1977, 1495-1496.
55. Kudo, K.; Sugita, N.; Takezaki, Y. Nihon Kagaku Kaishi 1977, 302-309.
56. Hashimoto, H.; Inoue, Y. Japan Kokai Tokkyo Koho 7 612,1978.
57. Yamaji, T. Japan Kokai Tokkyo Koho 166 146, 1981.
58. Yamaji, T. Japan Kokai Tokkyo Koho 140 948, 1981.
59. Gassner, F.; Leitner, W. J. Chem. Soc., Chem. Commun. 1993, 1465-1466.
60. Jessop, P. G.; Ikariya, T.; Noyori, R. Nature 1994, 368, 231-233.
61. Drury, D. J.; Hamlin, J. E. Eur. Patent Appl. 0 095 321, 1983.
62. Sakamoto, M.; Shimizu, I.; Yamamoto, A. Organometallics 1994, 13, 407-409.
63. Anderson, J. J.; Hamlin, J. E. Eur. Patent Appl. 0 126 524,1984.
64. Anderson, J. J.; Drury, D. J.; Hamlin, J. E.; Kent, A. G. Eur. Patent Appl. 0 181 078, 1986.
65. Tsai, J.-C.; Nicholas, K. M. J. Am. Chem. Soc. 1992,114, 5117-5124. Chemical Reviews, 1995, Vol. 95, No. 2 271
66. Khai, B. T.; Arcelli, A. J. Organomet. Chem. 1986, 309, C63-C66.
67. Taqui Khan, M. M.; Halligudi, S. B.; Shukla, S. J. Mol. Catal. 1989, 57, 47-60.
68. Klingler, R. J.; Krause, T. R.; Rathke, J. W. Catal. Lett. 1989, 3, 347-358.
69. Laine, R. M.; Rinker, R. G.; Ford, P. C. J. Am. Chem. Soc. 1977, 99, 252-253.
70. Burgemeister, T.; Kastner, F.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 739-741.
71. Ikariya, T.; Jessop, P. G.; Noyori, R., Japan Patent Appl. No. 27 4721, 1993.
72. Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. in press.
73. Nguyen, M. T.; Ha, T.-K. J. Am. Chem. Soc. 1984, 106, 599-602.
74. Sakaki, S.; Aizawa, T.; Koga, N.; Morokuma, K.; Ohkubo, K. Inorg. Chem. 1989, 28, 103-109.
75. Yoshida, T.; Thorn, D. L.; Okano, T.; Ibers, J. A.; Otsuka, S. J. Am. Chem. Soc. 1979, 101, 4212-4221.
76. Phala, H.; Kudo, K.; Mori, S.; Sugita, N. Bull. Inst. Chem. Res., Kyoto Univ. 1985, 63, 63-71.
77. Grushin, V. V. Acc. Chem. Res. 1993, 26, 279-286.
78. Karsch, H. H. Chem. Ber. 1977, 110, 2213-2221.
79. Koinuma, H.; Yoshida, Y.; Hirai, H. Chem. Lett. 1975, 1223-1226.
80. Darensbourg, D. J.; Ovalles, C. J. Am. Chem. Soc. 1984, 106, 3750-3754.
81. Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992,121, 155-284.
82. James, B. R. In Comprehensive Organometallic Chemistry, Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 285-369.
83. Denise, B.; Sneeden, R. P. A. CHEMTECH 1982, 12, 108-112.
84. Hawecker, J.; Lehn, J.-M.; Ziessel, R. Helv. Chim. Acta 1986, 69, 1990-2012.
85. Matsuoka, S.; Yamamoto, K.; Ogata, T.; Kusaba, M.; Nakashima, N.; Fujita, E.; Yanagida, S. J. Am. Chem. Soc. 1993,115, 601-609.
86. Leitner, W.; Brown, J. M.; Brunner, H. J. Am. Chem. Soc. 1993, 115, 152-159.
87. Denise, B.; Sneeden, R. P. A. J. Organomet. Chem. 1981, 221, 111-116.
88. Tominaga, K.; Sasaki, Y.; Kawai, M.; Watanabe, T.; Saito, M. J. Chem. Soc., Chem. Commun. 1993, 629-631.
89. Tominaga, K.; Sasaki, Y.; Hagihara, K.; Watanabe, T.; Saito, M. Chem. Lett. 1994, 1391-1394.
90. Vaska, L.; Schreiner, S.; Felty, R. A.; Yu, J. Y. J. Mol. Catal. 1989, 52, L11-L16.
91. Pruett, R. L.; Kacmarcik, R. T. Organometallics 1982,1, 1693-1699.
92. Cheong, M.; Lee, S. H.; Sa, Y. S.; Lee, J. S.; Kim, Y. G. J. Mol. Catal. 1991, 68, 277-288.
93. Weissermel, K.; Arpe, H.-J. Industrial Organic Chemistry, 2nd ed.; VCH: Weinheim, 1993; pp 39-43.
94. Kolomnikov, I. S.; Lobeeva, T. S.; Vol'pin, M. E. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 2329-2330.
95. Evans, G. O.; Newell, C. J. Inorg. Chim. Acta 1978, 31, L387-L389.
96. Darensbourg, D. J.; Ovalles, C.; Pala, M. J. Am. Chem. Soc. 1983, 105, 5937-5939.
97. Inoue, Y.; Sasaki, Y.; Hashimoto, H. J. Chem. Soc., Chem. Commun. 1975, 718-719.
98. Hashimoto, H.; Inoue, Y. Japan Kokai Tokkyo Koho 138 614, 1976.
99. Lodge, P. G.; Smith, D. J. H. Eur. Patent Appl. 0 094 785, 1983.
100. Darensbourg, D. J.; Ovalles, C. J. Am. Chem. Soc. 1987, 109, 3330-3336.
101. Jenner, G.; Nahmed, E. M.; Libs-Konrath, S. J. Mol. Catal. 1991, 64, 337-347.
102. Beguin, B.; Denise, B.; Sneeden, R. P. A. J. Organomet. Chem. 1981, 208, C18-C20.
103. Hoskins, B. F.; Steen, R. J.; Turney, T. W. Inorg. Chim. Acta 1983, 77, L69-L71.
104. Piacenti, F.; Bianchi, M. In Organic Syntheses via Metal Carbonyls; Wender, I., Pino, P., Eds.; John Wiley & Sons: New York, 1977; Vol. 2, pp 1-42.
105. Darensbourg, D. J.; Ovalles, C. CHEMTECH 1985, 15, 636-640.
106. Ashworth, T. V.; Singleton, E. J. Chem. Soc., Chem. Commun. 1976, 204-205.
107. Ashworth, T. V.; Nolte, M.; Singleton, E. J. Organomet. Chem. 1976, 121, C57-C60.
108. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum; New York, 1991.
109. Bipp, H.; Kieczka, H. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Ravenscroft, M., Rounsaville, J. F., Schulz, G., Eds.; VCH: Weinheim, 1989; Vol. A12, pp 1-12.
110. Schreiner, S.; Yu, J. Y.; Vaska, L. J. Chem. Soc., Chem. Commun. 1988, 602-603.
111. Haynes, P.; Slaugh, L. H.; Kohnle, J. F. Tetrahedron Lett. 1970, 365-368.
112. Haynes, P.; Kohnle, J. F.; Slaugh, L. H. US Patent 3 530 182, 1970.
113. Kiso, Y.; Saeki, K. Japan Kokai Tokkyo Koho 36 617, 1977.
114. Phala, H.; Kudo, K.; Sugita, N. Bull. Inst. Chem. Res., Kyoto Univ. 1981, 59, 88-105.
115. Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 8851-8852.
116. Schreiner, S.; Yu, J. Y.; Vaska, L. Inorg. Chim. Acta 1988,147, 139-141.
117. Tkatchenko, I. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 101-223.
118. Coleman, G. H.'; Alvarado, A. M. In Organic Syntheses; Gilman, H., Ed.; John Wiley & Sons: New York, 1941; Vol. 1, pp 3-4.
119. Benz, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 381-417.
120. Mitchell, J. A.; Reid, E. E. J. Am. Chem. Soc. 1931, 53, 1879-1883.
121. Theodoropulos, S. Eur. Patent Appl. 0 062 161, 1982. Jessop et al.
122. Wright, H. B.; Moore, M. B. J. Am. Chem. Soc. 1948, 70, 3865-3866.
123. Takeshita, K.; Kitamoto, A. J. Chem. Eng. Jpn. 1988, 21, 411-417.
124. Broadbent, H. S.; Bartley, W. J. J. Org. Chem. 1963, 28, 2345-2347.
125. Inoue, S.; Aida, T. In Comprehensive Polymer Science; Allen, G., Bevington, J. C., Eds.; Pergamon Press: Oxford, 1989; Vol. 3, pp 553-569.
126. Matsuda, H.; Ninagawa, A.; Nomura, R.; Tsuchida, T. Chem. Lett. 1979, 573-574.
127. Nomura, R.; Ninagawa, A.; Matsuda, H. J. Org. Chem. 1980, 45, 3735-3738.
128. De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157-158.
129. Koinuma, H.; Kato, H.; Hirai, H. Chem. Lett. 1977, 517-520.
130. Reid, R. C.; Prausnitz, J. M.; Poling, B. E. The Properties of Gases and Liquids, 4th ed.; McGraw-Hill Inc.: New York, 1987.
131. Bartle, K. D.; Clifford, A. A.; Jafar, S. A.; Shilstone, G. F. J. Phys. Chem. Ref. Data 1991, 20, 713-756.
132. Tsang, C. Y.; Streett, W. B. Chem. Eng. Sci. 1981, 36, 993-1000.