Supramolecular triruthenium cluster-based benzene hydrogenation catalysis: Fact or fiction?

Organometallics

Volumn 24, Issue 8, 2005, Pages 1819-1831

  Hagen, Collin M ^a   Vieille Petit, Ludovic ^b   Laurenczy, Gábor ^c   Süss Fink, Georg ^b   Finke, Richard G ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITÉ DE NEUCHÂTEL   (Switzerland)

^c EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

KINETIC METHODS; NANOCLUSTER FORMATION; REACTION CONDITIONS; TOTAL TURNOVER (TTO);

BENZENE; CATALYSTS; DISSOCIATION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; POSITIVE IONS; REACTION KINETICS; REDUCTION; RUTHENIUM; SUPRAMOLECULAR CHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY; X RAY PHOTOELECTRON SPECTROSCOPY;

CATALYSIS;

EID: 17244362738     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om048976y     Document Type: Article

References (97)

1. Lehn, J. M. Supramolecular Chemistry, Concepts and Perspectives; VCH Publishers: Weinheim, 1995. See pp 1-9 for Lehn's definitions and descriptions of supramolecular chemistry in which key notions are noncovalent, intermolecular interactions between molecules to achieve higher molecular assemblies capable of doing new chemistry.
2. (a) Süss-Fink, G.; Faure, M.; Ward, T. R. Angew. Chem., Int. Ed. 2002, 41, 99.
3. 4].
4. (c) Vieille-Petit, L.; Themen, B.; Süss-Fink, G.; Ward, T. R. J. Organomet. Chem. 2003, 684, 117.
5. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
6. (a) Supramolecular Cluster Catalysis, Science and Technology Concentrates. Chem. Eng. News 2002, Jan 14, 22.
7. 2a ("There can't be many more mechanistic surprises in catalytic hydrogenations!"),
8. 2
9. Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 191, 187.
10. Weddle, K. S.; Aiken, J. D., III; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 5653.
11. +-stabilized Rh nanocluster catalysts): Widegren, J. A.; Finke, R. G. Inorg. Chem. 2002, 41, 1558.
12. 12 for the interested reader,
13. n colloids are the true catalysts derived from Ruorganometallic precatalysts is a current issue in interesting recent work aimed at finding a practical lignin hydrogenation catalyst: Wong, T. Y. H.; Pratt, R.; Leong, C. G.; James, B. R.; Hu, T. Q. Chem. Ind. 2001, 82, 255 and references therein.
14. 9b The present work provides additional evidence for the uniqueness of Ian's chemistry,
15. (a) Rothwell, I. P. Chem. Commun. 1997, 1331.
16. (b) Chem. Eng. News 2004, June 7, 44.
17. 10b heterogeneous hydrogenation are: (a) Weissermel, K.; Arpe, H. J. Industrial Organic Chemistry, 2nd ed.; VCH: New York, 1993. (b) Aromatic Hydrogénation Catalysis: A Review. Stanislaus, A.; Cooper, B. H. Catal. Rev. Sci. Eng. 1994, 36, 75.
18. 10b heterogeneous hydrogenation are: (a) Weissermel, K.; Arpe, H. J. Industrial Organic Chemistry, 2nd ed.; VCH: New York, 1993. (b) Aromatic Hydrogénation Catalysis: A Review. Stanislaus, A.; Cooper, B. H. Catal. Rev. Sci. Eng. 1994, 36, 75.
19. Lead references to the more voluminous literature of the industrially important topic of the partial hydrogenation of benzene, with a focus on Ru heterogeneous catalysts, are: (a) Hu, S.-C.; Chen, Y.-W. Ind. Eng. Chem. Res. 2001, 40, 6099-6104. (b) Chen, Yu-Wen; Hu, Sung Cheng. J. Chin. Inst. Chem. Eng. 2000, 31, 529-532. (c) Hu, S.-C.; Chen, Y.-W. J. Chin. Inst. Chem. Eng. 1998, 29, 387-396. (d) Struijk, J.; Moene, R.; Van der Kamp, T.; Scholten, J. J. F. Appl. Catal., A 1992, 89, 77. (e) Struijk, J.; D'Angremond, M.; Lucas-De Regt, W. J. M.; Schölten, J. J. F. Appl. Catal., A 1992, 83, 263.
20. Lead references to the more voluminous literature of the industrially important topic of the partial hydrogenation of benzene, with a focus on Ru heterogeneous catalysts, are: (a) Hu, S.-C.; Chen, Y.-W. Ind. Eng. Chem. Res. 2001, 40, 6099-6104. (b) Chen, Yu-Wen; Hu, Sung Cheng. J. Chin. Inst. Chem. Eng. 2000, 31, 529-532. (c) Hu, S.-C.; Chen, Y.-W. J. Chin. Inst. Chem. Eng. 1998, 29, 387-396. (d) Struijk, J.; Moene, R.; Van der Kamp, T.; Scholten, J. J. F. Appl. Catal., A 1992, 89, 77. (e) Struijk, J.; D'Angremond, M.; Lucas-De Regt, W. J. M.; Schölten, J. J. F. Appl. Catal., A 1992, 83, 263.
21. Lead references to the more voluminous literature of the industrially important topic of the partial hydrogenation of benzene, with a focus on Ru heterogeneous catalysts, are: (a) Hu, S.-C.; Chen, Y.-W. Ind. Eng. Chem. Res. 2001, 40, 6099-6104. (b) Chen, Yu-Wen; Hu, Sung Cheng. J. Chin. Inst. Chem. Eng. 2000, 31, 529-532. (c) Hu, S.-C.; Chen, Y.-W. J. Chin. Inst. Chem. Eng. 1998, 29, 387-396. (d) Struijk, J.; Moene, R.; Van der Kamp, T.; Scholten, J. J. F. Appl. Catal., A 1992, 89, 77. (e) Struijk, J.; D'Angremond, M.; Lucas-De Regt, W. J. M.; Schölten, J. J. F. Appl. Catal., A 1992, 83, 263.
22. Lead references to the more voluminous literature of the industrially important topic of the partial hydrogenation of benzene, with a focus on Ru heterogeneous catalysts, are: (a) Hu, S.-C.; Chen, Y.-W. Ind. Eng. Chem. Res. 2001, 40, 6099-6104. (b) Chen, Yu-Wen; Hu, Sung Cheng. J. Chin. Inst. Chem. Eng. 2000, 31, 529-532. (c) Hu, S.-C.; Chen, Y.-W. J. Chin. Inst. Chem. Eng. 1998, 29, 387-396. (d) Struijk, J.; Moene, R.; Van der Kamp, T.; Scholten, J. J. F. Appl. Catal., A 1992, 89, 77. (e) Struijk, J.; D'Angremond, M.; Lucas-De Regt, W. J. M.; Schölten, J. J. F. Appl. Catal., A 1992, 83, 263.
23. Lead references to the more voluminous literature of the industrially important topic of the partial hydrogenation of benzene, with a focus on Ru heterogeneous catalysts, are: (a) Hu, S.-C.; Chen, Y.-W. Ind. Eng. Chem. Res. 2001, 40, 6099-6104. (b) Chen, Yu-Wen; Hu, Sung Cheng. J. Chin. Inst. Chem. Eng. 2000, 31, 529-532. (c) Hu, S.-C.; Chen, Y.-W. J. Chin. Inst. Chem. Eng. 1998, 29, 387-396. (d) Struijk, J.; Moene, R.; Van der Kamp, T.; Scholten, J. J. F. Appl. Catal., A 1992, 89, 77. (e) Struijk, J.; D'Angremond, M.; Lucas-De Regt, W. J. M.; Schölten, J. J. F. Appl. Catal., A 1992, 83, 263.
24. Widegren J. A.; Finke, R. G. J. Mol. Catal. 2003, 198, 317-341 ("A review of the problem of distinguishing true homogeneous catalysis from soluble or other metal-particle heterogeneous catalysis under reducing conditions"). Table S1 of the Appendix of that review lists >30 catalyst systems for which metal-particle heterogeneous catalysts are suspected to be the true catalysts.
25. Widegren, J. A.; Bennett, M. A.; Finke, R. G. J. Am. Chem. Soc. 2003, 125, 10301.
26. Hagen, C.; Widegren J. A.; Maitlis, P. M.; Finke, R. G. J. Am. Chem. Soc. 2005, in press.
27. 14
28. Dyson, P. J. Dalton Trans. 2003, 2964.
29. 5,6 hydrogenation catalyst."
30. 18ij helps document. Hence, there are already some, albeit infrequent, established cases of outersphere hydrogenation mechanisms in homogeneous catalysis,
31. (b) James, B. R. In Homogeneous Hydrogenation; J. Wiley: New York, 1973; Chapter VIII, p 314.
32. (c) Pryor, W. A. ACS Symp. Ser. 1978, 69, 33.
33. (d) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1979, 18, 173.
34. (e) Rüchardt, C.; Gerst, M.; Ebenhoch, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1406.
35. (f) Noyori, R.; Masashi, Y.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931.
36. (g) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40. Yamakawa, M.
37. (h) Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466.
38. (i) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998.
39. (j) Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.; Havana, M. J. Am. Chem. Soc. 2001, 123, 1090.
40. Relevant to non-d-orbital mechanisms of hydrogenation is, of course, the interesting example of nature's all-metal-free, organic-ligand-based hydrogenation system that, by definition, is free from any d-orbital influence: Reactions with Molecular Hydrogen in Microorganisms: Evidence for a Purely Organic Hydrogenation Catalyst: Thauer, R. K.; Klein, A. R.; Hartmann, G. C. Chem. Rev. 1996, 96, 3031.
41. (a) Taube, H.; Gould, E. S. Acc. Chem. Res. 1969, 2, 321.
42. (b) Haim, A. Acc. Chem. Res. 1975, 8, 264.
43. (c) Weaver, M. J. Inorg. Chem. 1979, 18, 402.
44. (d) Rotzinger, F. P.; Kumar, K.; Endicott, J. F. Inorg. Chem. 1982, 21, 4111.
45. (e) Sutin, N. J. Phys. Chem. 1986, 90, 3465.
46. (f) Reimers, J. R.; Hush, N. S. In Electron and Ion Transfer in Condensed Media: Theoretical Physics for Reaction Kinetics; Kornyshev, A. A., Tosi, M., Ulstrup, J., Eds.; World Scientific: Singapore, 1997; pp 326-346.
47. Lin, Y.; Finke, R. G. Inorg. Chem. 1994, 33, 4891.
48. (a) Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 1334.
49. (b) Jaska, C. A.; Manners, I. J. Am Chem. Soc. 2004, 126, 9776.
50. (a) Yu, K.; Sommer, W.; Weck, M.; Jones, C. W. J. Catal. 2004, 226, 101.
51. (b) Yu, K.; Sommer, W.; Richardson, J. M.; Week, M.; Jones, C. W. Adv. Synth. Catal. 2005, 347, 161.
52. Halpern, J. Inorg. Chim. Acta. 1981, 50, 11.
53. Halpern, J.; Okamoto, T.; Zakhariev, A. J. Mol. Catal. 1977, 2, 65.
54. The following results were obtained at Neuchâtel University: (i) the finding that complex 1 made at Neuchâtel University yields identical kinetic results when used at CSU; (ii) the finding that the same autocatalytic kinetics diagnostic of nanocluster formation are seen in experiments done at Neuchâtel University; (iii) the finding that bulk Ru(0) metal is also observed as a product in Neuchâtel University experiments; and (iv) the finding that such bulk metal is a kinetically competent catalyst. The H/D exchange NMR experiments for complex 1 were performed at the Ecole Polytechnique Fédérale de Lausanne.
55. Moulder, J. F.; Stickle, W. F.; Sobol, P. E.; Bomben, K. D. Handbook of X-ray Photoelectron Spectroscopy; Physical Electronics, Inc.: Eden Prairie, MN, 1995.
56. 21 and not a focus of, nor necessary for, the present work), (a) Aiken, J. D., III; Finke, R. G. Chem. Mater. 1999, 11, 1035. (b) Weddle, K. S.; Aiken, J. D., III; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 5653
57. 21 and not a focus of, nor necessary for, the present work), (a) Aiken, J. D., III; Finke, R. G. Chem. Mater. 1999, 11, 1035. (b) Weddle, K. S.; Aiken, J. D., III; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 5653
58. Özkar, S.; Finke, R. G. J. Organomet. Chem. 2004, 689, 403.
59. Özkar, S.; Finke, R. G. J. Am. Chem. Soc. 2002, 124, 5796.
60. Özkar, S.; Finke, R. G. Langmuir 2003, 19, 6247.
61. TEM beam damage is not a new problem: (a) Schmid published a review in the early 1990s showing that the TEM technique can cause metal atom rearrangements, cluster growth and aggregation, and ligand desorption from the metal surface. Schmid, G. Chem. Rev. 1992, 92, 1709. (b) Our 1999 review also reminds readers of these problems with TEM: Aiken, J. D., III; Finke, R. G. J. Mol. Catal. A: Chem. 1999, 145, 1. (c) See also ref 33.
62. TEM beam damage is not a new problem: (a) Schmid published a review in the early 1990s showing that the TEM technique can cause metal atom rearrangements, cluster growth and aggregation, and ligand desorption from the metal surface. Schmid, G. Chem. Rev. 1992, 92, 1709. (b) Our 1999 review also reminds readers of these problems with TEM: Aiken, J. D., III; Finke, R. G. J. Mol. Catal. A: Chem. 1999, 145, 1. (c) See also ref 33.
63. TEM beam damage is not a new problem: (a) Schmid published a review in the early 1990s showing that the TEM technique can cause metal atom rearrangements, cluster growth and aggregation, and ligand desorption from the metal surface. Schmid, G. Chem. Rev. 1992, 92, 1709. (b) Our 1999 review also reminds readers of these problems with TEM: Aiken, J. D., III; Finke, R. G. J. Mol. Catal. A: Chem. 1999, 145, 1. (c) See also ref 33.
64. 33b
65. (b) Williams, D. B.; Carter, C. B. Transmission Electron Microscopy; Plenum Press: New York, 1996.
66. Hornstein, B. J.; Finke, R. G. Chem. Mater. 2004, 16, 139.
67. 4, also provides a good fit to the data, Figure S5 of the Supporting Information. Whether or not the three- or four-step mechanism is best is not crucial in the present case, the fourth step serving only to confirm that the nanoclusters are not stable (i.e., that B + C → 1.5 C agglomeration occurs, Scheme S1 of the Supporting Information)
68. (b) Besson, C.; Finney, E. E.; Finke, R. G. Nanocluster Nucleation, Growth and Then Agglomeration Kinetic and Mechanistic Studies: A More General, Four-Step Mechanism Involving Double Autocatalysis, submitted for publication.
69. Watzky, M. A.; Finke, R. G. J. Am. Chem. Soc. 1997, 119, 10382.
70. Widegren, J. A.; Aiken, J. D., III; Özkar, S.; Finke, R. G. Chem. Mater. 2001, 13, 312.
71. 2]/dt = 40 psig/h), on which the main kinetic conclusions herein are based, have ≪20% MTL effects (if any) in those specific kinetics. In short, significant MTL effects are not complicating the kinetic-based conclusions reported herein,
72. (b) Aiken, J. D., III; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 9545.
73. The finding of an "autoxidation-initiated reduction catalyst" is important in its own right as an example of little appreciated autoxidation-product-initiated reactions:
74. (a) Weiner, H.; Finke, R. G. J. Am. Chem. Soc. 1999, 121, 9831.
75. (b) Yin, X.; Finke, R. G. Autoxidation-initiated Vanadium Catechol Dioxygenases, manuscript in preparation.
76. (a) Hornstein, B. J.; Aiken, J. D., III; Finke, R. G. Inorg. Chem. 2002, 41, 1625.
77. 2 poison inapplicable for the current 110°C benzene hydrogenation studies. This is why we developed the 1,10-phenanthroline and N-heterocyclic carbene poisons as part of the present work.
78. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
79. Kovács, G.; Nádasdi, L.; Joó, F.; Laurenczy, G. C. R. Acad. Sci. Paris, Chim. 2000, 3, 601.
80. Platt, J. R. Science 1964, 146, 347. This classic paper emphasizes the importance of multiple alternative hypotheses and disproof in science.
81. Hoffmann, R.; Minkin, V. I.; Carpenter, B. K. Bull. Soc. Chim. Fr. 1996, 133, 117.
82. 2, and instead store that Rh in the five detectable, nonproductive species,
83. 45h-k
84. (c) Professor R. G. Bergman, private communication, cited with permission,
85. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
86. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
87. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
88. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
89. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
90. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
91. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
92. (d) See Chapter 6, pp 531-541, and references therein, in: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (e) Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (f) Landis, C. R.; Rosaaen, K. A.; Kimberly, A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710. (g) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894. (h) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459. (i) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887. (j) Wu, Z.; Benedicte, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975. (k) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
93. Finke, R. G. In Metal Nanoparticles: Synthesis, Characterization, and Applications; Feldheim, D. L., Foss, C. A., Jr., Eds.; Marcel Dekker: New York, 2001; Chapter 2.
94. +, manuscript in preparation.
95. +, manuscript in preparation.
96. (a) Roe, D. C. J. Magn. Reson. 1985, 63, 388.
97. (b) Cusanelli, A.; Frey, U.; Richens, D. T.; Merbach, A. E. J. Am. Chem. Soc. 1996, 118, 5265.