Heterogeneous catalysis of C-C bond formation: Black art or organometallic science?

Chemical Communications

Volumn , Issue 1, 1996, Pages 1-8

  Maitlis, Peter M ^a   Long, Helen C ^a   Quyoum, Ruhksana ^a   Turner, Michael L ^a   Wang, Zhi Qiang ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345659531     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960000001     Document Type: Article

References (102)

1. G. A. Somorjai, An Introduction to Surface Chemistry and Catalysis, Wiley-Interscience, New York, 1994.
2. G. Suess-Fink and G. Meister, Adv. Organomet. Chem., 1993, 35, 41;
3. Metal Clusters in Catalysis, ed. B. C. Gates, L. Guczi and H. Knoezinger, Elsevier, Amsterdam, 1986;
4. R. M. Laine, J. Mol. Catal., 1982, 14, 137;
5. E. L. Muetterties and M. J. Krause, Angew. Chem., Int. Ed. Engl., 1983, 22, 135.
6. Surfaces in catalysis are not static but dynamic and ever-changing; this makes understanding and reproducibility even more challenging, G. Ertl, Adv. Catal., 1990, 37, 213.
7. G. W. Parshall and S. D. Ittel, Homogeneous Catalysis, Wiley-Interscience, New York, 1992.
8. 3; (benzene, 25°C). D. R. Neithamer, R. E. Lapointe, R. A. Wheeler, D. S. Richerson, G. D. van Duyne and P. T. Wolczanski, J. Am. Chem. Soc., 1989, 111, 9056;
9. see also F. Calderazzo, U. Englert, A. Guarini, F. Marchetti, G. Pamploni and A. Segre, Angew. Chem., Int. Ed. Engl., 1994, 33, 1188.
10. Arrays of metal atoms are involved cooperatively in electron transfer processes, especially biological ones, see for example, J. J. R. Frausto da Silva and R. J. P. Williams, The Biological Chemistry of the Elements, Clarendon Press, Oxford, 1991, p. 319 et seq.
11. P. M. Maitlis, The Organic Chemistry of Palladium, Academic Press, vol. 2 (Catalytic Reactions), 1972, p. 78;
12. P. M. Henry, Palladium Catalysed Oxidation of Hydrocarbons, Reidel, Dordrecht, 1980.
13. J. Skupinska, Chem. Rev., 1991, 91, 613.
14. See, for example, J. M. White, Langmuir, 1994, 10, 3946;
15. M. Xi and B. E. Bent, Langmuir, 1994, 10, 505;
16. F. Zaera, Acc. Chem. Res., 1992, 25, 260;
17. J. L. Lin, C. M. Chiang, C. J. Jenks, M. X. Yang, T. H. Wentzlaff and B. E. Bent, J. Catal., 1994, 147, 250.
18. P. Sabatier and J. B. Senderens, Compt. Rend., 1902, 134, 514, 689.
19. F. Fischer and H. Tropsch, Brennstoff-Chem., 1926, 7, 97;
20. Chem. Ber., 1926, 59, 830.
21. H. Pichler, Adv. Catal., 1952, 4, 271.
22. M. E. Dry, Catal. Today, 1990, 6, 183;
23. B. Jager and R. Espinoza, Catal. Today, 1995, 23, 17.
24. M. van der Burgt, J. van Klinken and T. Sie, The Shell Middle Distillate Synthesis Process, 5th Synfuels Worldwide Symposium, Washington DC, November 1985.
25. J. Haggin, Chem. Eng. News., 23rd July, 1990, p. 27.
26. M. A. Vannice, J. Catal., 1975, 37, 449.
27. M. Bhasin, W. J. Hartley, P. C. Ellgen and T. P. Wilson, J. Catal., 1978, 54, 120;
28. M. Ichikawa, Bull. Chem. Soc. Jpn., 1978, 51, 2273;
29. J. Catal., 1979, 56, 127;
30. P. R. Watson and G. A. Somorjai, J. Catal., 1981, 72, 347;
31. P. R. Watson and G. A. Somorjai, J. Catal., 1982, 74, 282;
32. B. J. Kip, E. G. F. Hermans, J. H. M. C. van Wolput, N. M. A. Haermans, J. van Grondelle and R. Prins, Appl. Catal., 1987, 35, 109;
33. J. C. Lavalley, J. Saussey, J. Lamotte, R. Breault, J. P. Hindermann and A. Kiennemann, J. Phys. Chem., 1990, 94, 5941;
34. see also, M. Bowker, Catal. Today, 1992, 15, 77.
35. P. R. Wentrcek, B. J. Wood and H. Wise, J. Catal., 1976, 43, 363;
36. M. Araki and V. Ponec, J. Catal., 1976, 44, 439;
37. J. A. Rabo, A. P. Risch and M. L. Poutsuma, J. Catal., 1978, 53, 295;
38. P. Biloen, J. N. Helle and W. M. H. Sachtler, J. Catal., 1979, 58, 95.
39. M. C. Kaminsky, N. Winograd, G. L. Geoffroy and M. A. Vannice, J. Am. Chem. Soc., 1986, 108, 1315.
40. D. F. Shriver and M. J. Sailor, Acc. Chem. Res., 1988, 21, 374;
41. J. S. Bradley, Adv. Organomet. Chem., 1983, 22, 1;
42. M. H. Chisholm, C. E. Hammond, V.J. Johnson, W. E. Streib and J. C. Huffman, J. Am. Chem. Soc., 1992, 114, 7056.
43. R. B. Anderson, The Fischer-Tropsch Reaction, Academic Press, London, 1984;
44. 1 Chemistry, ed. W. Keim, Reidel, Dordrecht, 1983;
45. see also R. A. Sheldon, in Chemicals from Synthesis Gas, Reidel, Dordrecht, 1983;
46. I. Wender and H. W. Sternberg, Adv. Catal., 1957, 9, 594;
47. H. Pichler and H. Schultz, Chem. Ing. Tech., 1970, 42, 1162.
48. E. Iglesia, S. C. Reyes, R. J. Madon and S. L. Soled, Adv. Catal., 1993, 39, 221.
49. P. Biloen, J. R. Neth. Chem. Soc., 1980, 99, 33;
50. P. Biloen and W. M. H. Sachtler, Adv. Catal., 1981, 30, 165.
51. R. C. Brady III and R. Pettit, J. Am. Chem. Soc., 1980, 102, 6181;
52. R. C. Brady III and R. Pettit, J. Am. Chem. Soc., 1981, 103, 1287.
53. L. E. McCandlish, J. Catal., 1983, 83, 362.
54. E. L. Hoel, G. B. Ansell and S. Leta, Organometallics, 1984, 3, 1633;
55. E. L. Hoel, G. B. Ansell and S. Leta, Organometallics, 1986, 5, 585;
56. E. L. Hoel, Organometallics, 1986, 5, 587.
57. Reviewed, in P. M. Maitlis, J. Organomet. Chem., 1995, 500, 239;
58. see also: K. Isobe, D. G. Andrews, B. E. Mann and P. M. Maitlis, J. Chem. Soc., Chem. Commun., 1981, 809;
59. K. Isobe, A. Vázquez de Miguel, P. M. Bailey, S. Okeya and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1983, 1441;
60. S. Okeya, N. J. Meanwell, B. F. Taylor, K. Isobe, A. Vásquez de Miguel and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1984, 1453.
61. 5 rings nor the solvents were involved in the formation of these organics: I. M. Saez, N. J. Meanwell, A. Nutton, K. Isobe, A. Vázquez de Miguel, D. W. Bruce, S. Okeya, D. G. Andrews, P. R. Ashton, I. R. Johnstone and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1986, 1565;
62. I. M. Saez, D. G. Andrews and P. M. Maitlis, Polyhedron, 1988, 7, 827;
63. P. M. Maitlis, I. M. Saez, N. J. Meanwell, K. Isobe, A. Nutton, A. Vázquez de Miguel, D. W. Bruce, S. Okeya, P. M. Bailey, D. G. Andrews, P. R. Ashton and I. R. Johnstone, New J. Chem., 1989, 13, 419.
64. J. M. Martinez, H. Adams, N. A. Bailey and P. M. Maitlis, J. Chem. Soc., Chem. Commun., 1989, 286;
65. J. Martinez, J. B. Gill, H. Adams, N. A. Bailey, I. M. Saez, G. J. Sunley and P. M. Maitlis, J. Organomet. Chem., 1990, 394, 583.
66. 2 species in Fischer-Tropsch reactions has been put forward by several authors: J. T. Kummer, W. B. Spencer, H. H. Podgurski and P. H. Emmett, J. Am. Chem. Soc., 1951, 73, 564;
67. J. T. Kummer and P. H. Emmett, J. Am. Chem. Soc., 1953, 75, 5177;
68. Y. Kobori, H. Yamasaki, S. Naito, T. Onishi and K. Tamaru, J. Chem. Soc., Faraday Trans. 1, 1982, 78, 1473;
69. R. Snel and R. L. Espinoza, J. Mol. Catal., 1987, 43, 237;
70. C. A. Mims, L. E., McCandlish and M. T. Melchior, Catal. Lett., 1988, 1, 121;
71. F. A. P. Cavalcanti, R. Oukaci, I. Wender and D. G. Blackmond, J. Catal., 1990, 123, 270;
72. C. A. Mims, J. J. Krajewski, K. D. Rose and M. T. Melchior, Catal. Lett., 1990, 7, 119;
73. K. R. Krishna and A. T. Bell, Catal. Lett., 1992, 14, 305.
74. M. L. Turner, H. C. Long, A. Shenton, P. K. Byers and P. M. Maitlis, Chem. Eur. J., 1995, 1, 549;
75. see also: F. Ma, G. J. Sunley, I. M. Saez and P. M. Maitlis, J. Chem. Soc., Chem. Commun., 1990, 1279;
76. M. L. Turner, P. K. Byers, H. C. Long and P. M. Maitlis, J. Am. Chem. Soc., 1993, 115, 4417.
77. D. L. Davies, M. J. Parrott, P. Sherwood and F. G. A. Stone, J. Chem. Soc., Dalton Trans., 1987, 1201.
78. H. C. Long, R. Quyoum, M. L. Turner and P. M. Maitlis, unpublished work.
79. 2)], S. A. R. Knox, J. Organomet. Chem., 1990, 400, 255;
80. J. Cluster Sci., 1992, 3, 385.
81. J. J. Low and W. A. Goddard, J. Am. Chem. Soc., 1984, 106, 6928, 8321;
82. Organometallics, 1986, 5, 609;
83. G. Trinquier and R. Hoffmann, Organometallics, 1984, 3, 370;
84. K. Tatsumi, R. Hoffmann, A. Yamamoto and J. K. Stille, Bull. Chem. Soc. Jpn., 1981, 54, 1857.
85. J. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organo-Transition Metal Chemistry, University Science Books, Mill Valley, CA, 1987, p. 322 et seq.;
86. E. R. Evitt and R. G. Bergman, J. Am. Chem. Soc., 1980, 102, 7003.
87. M. J. Calhorda, J. M. Brown and N. A. Cooley, Organometallics, 1991, 10, 1431.
88. Z-Q. Wang, H. C. Long, M. L. Turner and P. M. Maitlis, J. Chem. Soc., Chem. Commun., 1995, 1089.
89. Z-Q. Wang, M. L. Turner, R. Kunicki and P. M. Maitlis, J. Organomet. Chem., 1995, 488, C11.
90. See also ref. 34; C. Bohanna, M. A. Esteruelas, F. J. Lahoz, E. Onate, L. A. Oro and E. Sola, Organometallics, 1995, 14, 4825;
91. M. J. Burn, M. G. Fickes, F. J. Hollander and R. G. Bergman, Organometallics, 1995, 14, 137.
92. M. Bassetti, D. Monti, A. Haynes, J. M. Pearson, I. A. Stanbridge and P. M. Maitlis, Gazz. Chim. Ital., 1992, 122, 391;
93. J. M. Pearson, A. Haynes, G. E. Morris, G. J. Sunley and P. M. Maitlis, J. Chem. Soc., Chem. Commun., 1995, 1045.
94. Z-Q. Wang and P. M. Maitlis, unpublished work.
95. See also: A. Pedersen and M. Tilset, Organometallics, 1993, 12, 56;
96. A. Pedersen and M. Tilset, Organometallics, 1994, 13, 4887.
97. X. L. Zhou, A. L. Schwaner and J. M. White, J. Am. Chem. Soc., 1993, 115, 4309;
98. X. L. Zhou and J. M. White, J. Phys. Chem., 1992, 96, 7703, and also on Cu(100),
99. M. X. Yang, J. Eng, P. W. Kash, G. W. Flynn, B. E. Bent, M. T. Holbrook, S. R. Bare, J. L. Gland and D. A. Fischer, J. Phys. Chem., submitted, we thank Professor Bent for a preprint.
100. V. C. Gibson, G. Parkin and J. E. Bercaw, Organometallics, 1991, 10, 220.
101. R. W. Joyner, Catal. Lett., 1988, 1, 307.
102. P. S. Cremer and G. A. Somorjai, J. Chem. Soc., Faraday Trans., 1995, 91, 3671.