Coordination copolymerization of severely encumbered isoalkenes with ethylene: Enhanced enchainment mediated by binuclear catalysts and cocatalysts

Journal of the American Chemical Society

Volumn 127, Issue 42, 2005, Pages 14756-14768

  Li, Hongbo ^a   Li, Liting ^a   Schwartz, David J ^a   Metz, Matthew V ^a   Marks, Tobin J ^a   Liable Sands, Louise ^b   Rheingold, Arnold L ^b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COPOLYMERS; MONOMERS; OLEFINS; ORGANOMETALLICS; SOLVENTS;

BISBORANE ACTIVATORS; CATALYST-COCATALYSTS; COMONOMER ENCHAINMENT; ION PAIRING;

COPOLYMERIZATION;

2 METHYL 2 BUTENE DERIVATIVE; ALKENE; ALKENE DERIVATIVE; BORANE DERIVATIVE; BUTENE; COORDINATION COMPOUND; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; ETHYLENE; ION; METHYLENECYCLOHEXANE; METHYLENECYCLOPENTANE; POLYETHYLENE; SOLVENT; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; GEOMETRY; ION TRANSPORT; POLYMERIZATION;

ALKENES; CARBON ISOTOPES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ETHYLENES; MAGNETIC RESONANCE SPECTROSCOPY; METALS, HEAVY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 27144469261     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052995x     Document Type: Article

References (160)

1. (a) Collman, J. P.; Boulatov, R.; Sunderland, C. J.; Fu, L. Chem. Rev. 2004, 104, 561-588.
2. (b) Krishnan, R.; Voo, J. K.; Riordan, C. G.; Zahkarov, L.; Rheingold, A. L. J. Am. Chem. Soc. 2003, 125, 4422-4423.
3. (c) Bruice, T. C. Acc. Chem. Res. 2002, 35, 139-148.
4. (d) Bruice, T. C.; Benkovic, S. J. Biochemistry 2000, 39, 6267-6274 and references therein.
5. (e) O'Brien, D. P.; Entress, R. M. N.; Matthew, A. C.; O'Brien, S. W.; Hopkinson, A.; Williams, D. H. J. Am. Chem. Soc. 1999, 121, 5259-5265.
6. (f) Carazo-Salas, R. E.; Guarguaglini, G.; Gruss, O. J.; Segref, A.; Karsenti, E.; Mattaj, L. W. Nature 1999, 400, 178-181.
7. (g) Menger, F. M. Acc. Chem. Res. 1993, 26, 206-212 and references therein.
8. (h) Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: New York, 1984; pp 1-54.
9. (a) Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928-9929.
10. (b) Moore, D. R.; Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2003, 125, 11911-11924.
11. (c) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410-2411.
12. (d) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
13. (e) Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75-86.
14. (f) Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780-10781.
15. (g) Molenveld, P.; Kapsabelis, S.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1997, 119, 2948-2949.
16. (h) Mathews, R. C.; Howell, D. H.; Peng, W.-J.; Train, S. G.; Treleaven, W. D.; Stanley, G. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2253-2256.
17. (i) Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309-3310.
18. For recent reviews of single-site olefin polymerization, see: (a) Kaminsky, W. J. Polym. Sci., Part B: Polym. Chem. 2004, 42, 3911-3921.
19. (b) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-316.
20. (c) Pedeutour, J.-N.; Radhakrishnan, K.; Cramail, H.; Deffieux, A. Macromol. Rapid Commun. 2001, 22, 1095-1123.
21. (d) Gladysz, J. A. Chem. Rev. 2000, 100 (special issue on Frontiers in Metal-Catalyzed Polymerization).
22. (e) Marks, T. J.; Stevens, J. C. Top. Catal. 1999, 15, and references therein.
23. (f) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428-447.
24. (g) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144-187.
25. (h) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270.
26. (i) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170.
27. (j) Catalyst Design for Tailor-Made Polyolefins; Soga, K., Terano, M., Eds.; Elsevler: Tokyo, 1994.
28. (k) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65.
29. For studies of binuclear metallocenes, see: (a) Li, H.; Li, L.; Marks, T. J. Angew. Chem., Int. Ed. 2004, 37, 4937-4940.
30. (b) Wang, J.; Li, H.; Guo, N.; Li, L.; Stern, C. L.; Marks, T. J. Organometallics 2004, 23, 5112-5114.
31. (c) Guo, N.; Li, L.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 6542-43.
32. Li, H.; Li, L.; Marks, T. J.; Liable-Sands, L.; Rheingold, A. L. J. Am. Chem. Soc. 2003, 125, 10788-10789.
33. (e) Noh, S. K.; Lee, J.; Lee, D. J. Organomet. Chem. 2003, 667, 53-60.
34. (f) Li, L.; Metz, M. V.; Li, H.; Chen, M.-C.; Marks, T. J.; Liable-Sands, L.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12725-12741.
35. (g) Abramo, G. P.; Li, L.; Marks, T. J. J. Am. Chem. Soc. 2002, 124, 13966-13967.
36. (h) Green, M. L. H.; Popham, N. H. J. Chem. Soc., Dalton Trans. 1999, 1049-1059 and references therein.
37. (i) Spaleck, W.; Kuber, F.; Bachmann, B.; Fritze, C.; Winter, A. J. Mol. Catal. A: Chem. 1998, 128, 279-287.
38. (j) Van, X.; Chernega, A.; Green, M. L. H.; Sanders, J.; Souter, J.; Ushioda, T. J. Mol. Catal. A: Chem, 1998, 128, 119-141.
39. (k) Soga, K.; Ban, H. T.; Uozumi, T. J. Mol. Catal. A: Chem. 1998, 128, 273-278.
40. (l) Bochmann, M.; Cuenca, T.; Hardy, D. T. J. Organomet. Chem. 1994, 484, C10-C12.
41. (a) Chum, P. S.; Kruper, W. J.; Guest, M. J. Adv. Mater. 2000, 12, 1759-1767.
42. (b) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598.
43. (c) Harrison, D.; Coulter, I. M.; Wang, S. T.; Nistala, S.; Kuntz, B. A.; Pigeon, M.; Tian, J.; Collins, S. J. Mol. Catal. A: Chem. 1998, 128, 65-77.
44. (d) Soga, K.; Uozumi, T.; Nakamura, S.; Toneri, T.; Teranishi, T.; Sano, T.; Arai, T.; Shiono, T. Macromol. Chem. Phys. 1996, 197, 4237-4251.
45. (e) Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132-3134.
46. (f) Lai, S. Y.; Wilson, J. R.; Knight, G. W.; Stevens, J. C. WO-93/08221, 1993.
47. (g) Canich, J. M.; Hlatky, G. G.; Turner, H. W. PCT Appl. WO-92/00333, 1992;
48. Canich, J. M. Eur. Patent Appl. EP420436-A1, 1991 (Exxon Chemical Co.).
49. (h) Devore, D. D. European Patent Application EP-514-828-A1, November 25, 1992.
50. Similar bifunctional cocatalysts: (a) Lewis, S. P.; Henderson, L. D.; Chandler, B. D.; Parvez, M.; Piers, W. E.; Collins. S. J. Am. Chem. Soc. 2005, 127, 46-47.
51. (b) Lewis, S. P.; Taylor, N. J.; Piers, W. E.; Collins, S. J. Am. Chem. Soc. 2003, 125, 14686-14687.
52. (c) Metz, M. V.; Schwartz, D. J.; Stern, C. L.; Marks, T. J.; Nickias, P. N. Organometallics 2002, 21, 4159-4168.
53. (d) Lancaster, S. J.; Rodriguez, A.; Lara-Sanchez, A.; Hannant, M. D.; Walker, D. A.; Hughes, D. H.; Bochmann, M. Organometallics 2002, 21, 451-453.
54. (e) McAdon, M. H.; Nickias, P. N.; Marks, T. J.; Schwartz, D. J. WO9906413A1, February 11, 1999.
55. (f) Metz, M. V.; Schwartz, D. J.; Stern, C. L.; Nickias, P. N.; Marks, T. J. Angew. Chem., Int. Ed. 2000, 39, 1312-1316.
56. (g) Williams, V. C.; Piers, W. E.; Clegg, W.; Elsegood, M. R. J.; Collins, S.; Marder, T. B. J. Am. Chem. Soc. 1999, 121, 3244-3245.
57. (h) Jia, L.; Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 842-857.
58. (a) Jensen, T. R.; O'Donnell, J. J., III; Marks, T. J. Organometallics 2004, 23, 740-754.
59. (b) Jia, L.; Yang, X. M.; Seyam, A. M.; Albert, I. D. L.; Fu, P. F.; Yang, S. T.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 7900-7913.
60. (c) Jia, L.; Yang, X. M.; Yang, S. T.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 1547-1548.
61. (d) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625-4626.
62. (e) Yang, X. M.; Jia, L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392-3393.
63. (a) Takeuchi, D.; Anada, K.; Osakada, K. Macromolecules 2002, 55, 9628-9633.
64. (b) Takeuchi, D.; Osakada, K. Chem. Commun. 2002, 646-467.
65. (c) Takeuchi, D.; Kim, S.; Osakada, K. Angew. Chem., Int. Ed. 2001, 14, 2685-2688.
66. (a) Kulshrestha, A. K.; Talapatra, S. In Handbook of Polyolefins; Vasile, C., Ed; Marcel Dekker: New York, 2000.
67. (b) McKnight, A. L.; Waymouth, R. M. Macromolecules 1999, 32, 2816-2825.
68. (c) Natori, I.; Imaizumi, K.; Yamagishi, H.; Kazunori, M. J. Polym. Sci., Part B: Polym. Phys. 1998, 36, 1657-1668.
69. (d) Natori, I. Macromolecules 1997, 30, 3696-3697.
70. (e) Cherdron, H.; Brekner, M.-J.; Osan, F. Angew. Makromol. Chem. 1994, 225, 121-133.
71. (f) James, D. E. In Encyclopedia of Polymer Science and Engineering; Marks, H. F., Bikales, N. M., Overberger, C. G., Menges, G., Eds.; Wiley-Interscience: New York, 1985; Vol. 6.
72. (a) Zhao, J.; Hahn, S. F.; Hucul, D. A.; Meunier, D. M. Macromolecules 2001, 34, 1737-1741.
73. (b) Hucul, D. A.; Hahn, S. F. Adv. Mater. 2000, 12, 1855-1858.
74. (a) Hahn, S. F.; Hillmyer, M. A. Macromolecules 2003, 36, 71-76.
75. (b) Ness, J. S.; Brodil, J. C.; Bates, F. S.; Hahn, S. F.; Hucul, D. A.; Hillmyer, M. A. Macromolecules 2002, 35, 602-609.
76. (c) Gehlsen, M. D.; Weimann, P. A.; Bates, F. S.; Mays, J. J. Polym. Sci., Part B: Polym. Phys. 1995, 33, 1527-1536.
77. (d) Gehlsen, M.; Bates, F. S. Macromolecules 1993, 26, 4122-4127.
78. Detailed synthetic and characterization data can be found in the Supporting Information.
79. (a) Song, F.; Lancaster, S. J.; Cannon, R. D.; Schormann, M.; Humphrey, S. M.; Zuccaccia, C.; Macchioni, A.; Bochmann, M. Organometallics 2005, 24, 1315-1328.
80. (b) Hannig, F.; Frohlich, R.; Bergander, K.; Erker, G.; Petersen, J. L. Organometallics 2004, 23, 4495-4502.
81. (c) Beck, S.; Lieber, S.; Schaper, F.; Geyer, A.; Brintzinger, H. H. J. J. Am. Chem. Soc. 2001, 123, 1483-1489.
82. (d) Chase, P. A.; Piers, W. E.; Patrick, B. O. J. Am. Chem. Soc. 2000, 122, 12911-12912.
83. (e) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-10031.
84. (f) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 3623-2625.
85. (g) Bochmann, M.; Lancaster, S. J.; Hursthouse, M. B.; Abdul Malik, K. M. Organometallics 1994, 13, 2235-2243.
86. (h) Stahl, N. G.; Salata, M. R.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 10898-10909.
87. (a) Christopher, J. N.; Jordan, R. F.; Petersen, J. L.; Young, V. G., Jr. Organometallics 1997, 16, 3044-3050.
88. (b) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4030-4037.
89. (c) Christopher, J. N.; Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4038-4044.
90. (d) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4045-4053.
91. (e) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1996, 118, 8024-8033.
92. (f) Carpenetti, D. W.; Kloppenburg, L.; Kupec, J. T.; Petersen, J. L. Organometallics 1996, 15, 1572-1581.
93. (g) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, U.K., 1980; pp 500-502.
94. (h) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273-280.
95. Barlos, K.; Huebler, G.; Noth, H.; Wanninger, P.; Wiberg, N.; Wrackmeyer, B. J. Magn. Reson. 1978, 31, 363-376.
96. (a) Klosin, J.; Kruper, W. J., Jr.; Nickias, P. N.; Roof, G. R.; De Waele, P.; Abboud, K. A. Organometallics 2001, 20, 2663-2665.
97. (b) Park, J. T.; Yoon, S. C.; Bae, B.-J.; Seo, W. S.; Suh, I.-H.; Han, T. K.; Park, J. R. Organometallics 2000, 19, 1269-1276.
98. (c) Feng, S.; Klosin, J.; Kruper, W. J., Jr.; McAdon, M. H.; Neithamer, D. R.; Nickias, P. N.; Patton, J. T.; Wilson, D. R.; Abboud, K. A.; Stern, C. L. Organometallics 1999, 18, 1159-1167.
99. (d) McKnight, A. L.; Masood, M. A.; Waymouth, R. M.; Straus, D. A. Organometallics 1997, 16, 2879-2885.
100. (a) Zuccaccia, C.; Stahl, N. G.; Macchioni, A.; Chen, M.-C.; Roberts, J. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 1448-1464.
101. (c) Beswick, C. L.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 10358-10370.
102. (d) Deck, P. A.; Beswick, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1772-1784.
103. (a) Lanza, G.; Fragala, I. L.; Marks, T. J. Organometallics 2002, 21, 5594-5612.
104. (b) Lanza, G.; Fragala, I. L.; Marks, T. J. Organometallics 2001, 20, 4006-4017.
105. (c) Lanza, G.; Fragala, I. L.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 12764-12777.
106. Fu, P.; Marks, T. J. Unpublished results.
107. Guzei, I. A.; Stockland, R. A.; Jordan, R. F. Acta Crystallogr. 2000, C56, 635-636.
108. 21b,c
109. (b) Baird, M. C. Chem. Rev. 2000, 100, 1471-1478 and references therein.
110. (c) Barsan, F.; Karam, A. R.; Parent, M. A.; Baird, M. C. Macromolecules 1998, 31, 8439-8447.
111. (a) Breitmaier, E.; Voelter, W. Carbon-13 NMK Spectroscopy; VCH Publishers: Weinheim, Germany, 1987.
112. (b) Spectral Database for Organic Compounds, SDBS.
113. The assignment is based on relative intensity changes of these peaks at different incorporation levels.
114. 2- bridged analogue, presumably facilitating the cooperative enchainment effects. Li, H.; Stern, C. T.; Marks, T. J. Macromolecules, in press.
115. 24h under the present polymerization conditions (25 °C, 1 aim). (a) Yang, S. H.; Huh, J. H.; Jo, W. H. Macromolecules 2005, 38, 1402-1409.
116. (b) Chen, M.-C.; Roberts, J. A. S.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 4605-4625.
117. (c) Forlini, F.; Tritto, I.; Locatelli, P.; Sacchi, M. C.; Piemontesi, F. Makromol. Chem. Phys. 2000, 201, 401-408.
118. (d) Forlini, F.; Tritto, I; Locatelli, P.; Sacchi, M. C.; Piemontesi, F. Makromol. Chem. Phys. 2000, 201, 401-408.
119. (e) Kleinschmidt, R.; Griebenow, Y.; Fink, G. J. Mol. Catal. A-Chem. 2000, 157, 83-90.
120. (f) Coevoet, D.; Cramail, H.; Deffieux, A. Makromol. Chem. Phys. 1999, 200, 1208-1214.
121. (g) Atiqullah, M.; Hammawa, H.; Hamid, H. Eur Polym. J. 1998, 34, 1511-1520.
122. (h) Sahgal, A.; La, H. M.; Hayduk, W. Can. J. Chem, Eng. 1978, 56, 354-357.
123. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991; pp 215, 237-238.
124. Liu, Z.; Somsook, E.; White, C. B.; Rosaaen, K. A.; Landis, C. R. J. Am. Chem. Soc. 2001, 123, 11193-11207.
125. (a) Brandrup, J.; Immergut, E. H. Eds. Polymer Handbook, 2nd ed.; Wiley: New York, 1975; Chapter 111, pp 143-144, and also, for PE, Chapter V, p 16.
126. (b) Ferry, J. D. Viscoelastic Properties of Polymers, 2nd ed.; Wiley: New York, 1970; Tables 12-111.
127. Shaffer, T. D.; Canieh, J. M.; Squire, K. R. Macromolecules 1998, 31, 5145-5147. Here, ethylene + isobutene eopolymerizations mediated by a N-modified mononuclear CGCTi catalyst result in significant isobutene enchainment in cases where the feed is very isobutene-rich (isobutene: ethylene up to 150:1).
128. Johnston, N. W. J. Macromol. Sci., Rev. Macromol. Chem. 1976, C14, 215-250.
129. (a) King, W. A.; Marks, T. J. Inorg. Chim. Acta 1995, 229, 343-354.
130. (b) Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701-7715.
131. (a) Isaacs, N. S. Physical Organic Chemistry; Wiley: New York, 1987; pp 282-291.
132. (b) McMillan, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493-532.
133. (c) Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976; appendix.
134. Horton, A. D. Organometallics 1996, 15, 2675-2677.
135. Luo, L.; Marks, T. J. in ref 3e, pp 97-106.
136. Lide, D. R.; Kehiaian, H. V. CRC Handbook of Thermophysical and Thermochemical Data; CRC Press; Boca Raton, FL.
137. (a) Scherer, W.; McGrady, G. S. Angew. Chem., Int. Ed. 2004, 43, 1782-1806.
138. (b) Prosene, M. H.; Brintzinger, H. H. Organometallics 1997, 16, 3889-3894.
139. (e) Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85-93.
140. (d) Prosene, M. H.; Janiak, C.; Brintzinger, H. H. Organometallics 1992, 11, 4036-4041.
141. (e) Cotter, W. D.; Bercaw, J. E. J. Organomet. Chem. 1991, 417, C1-C6.
142. (f) Krauledat, H.; Brintzinger, H. H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1412-1413.
143. (g) Piers, W. E.; Bereaw, J. E. J. Am. Chem. Soc. 1990, 112, 9406-9407.
144. (h) Brookhart, M.; Green, M. L. H.; Wong, L. L. Prog. Inorg. Chem. 1988, 36, 1-124.
145. (i) Clawson, L.; Soto, J.; Buchwald, S. L.; Steigerwald, M. L.; Grubbs, R. H. J. Am. Chem. Soc. 1985, 107, 3377-3378.
146. (a) Casey, C. P.; Tunge, J. A.; Lee, T.-Y.; Pagan, M. A. J. Am. Chem. Soc. 2003, 125, 2641-2651.
147. (b) Landis, C. R.; Rosaaen, K. A.; Uddin, J. J. Am. Chem. Soc. 2002, 124, 12062-12063.
148. (e) Casey, C. P.; Lee, T.-Y.; Tunge, J. A.; Carpenetti, D. W., II. J. Am. Chem. Soc. 2001, 123, 10762-10763.
149. (d) Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85-93.
150. (a) Stoebenau, E. J., III; Jordan, R. F. J. Am. Chem. Soc. 2004, 126, 11170-11171.
151. (b) Stoebenau, E. J., III; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 3222-3223.
152. (e) Carpentier, J.-F.; Maryin, V. P.; Luci, J.; Jordan, R. F. J. Am. Chem. Soc. 2001, 123, 898-909.
153. Brandow, C. G.; Mendiratta, A.; Bereaw, J. E. Organometallics 2001, 20, 4253-4261.
154. (a) Bouwkamp, M. W.; de Wolf, J.; del Hierro Morales, I.; Gercama, J.; Meetsma, A.; Troyanov, S. I.; Hessen, B.; Teuben, J. H. J. Am. Chem. Soc. 2002, 124, 12956-12957.
155. (b) Kawabe, M.; Murata, M. Macromol. Chem. Phys. 2001, 202, 2440-2446.
156. (c) Rybtchinski, B.; Konstantinovsky, L.; Shimon, L. J. W.; Vigalok, A.; Milstein, D. Chem.-Eur. J. 2000, 6, 3287-3292.
157. (d) Carr, N.; Mole, L.; Orpena, A. G.; Spencer, G. L. J. Chem. Soc., Dalton Trans. 1992, 18, 2653-2662.
158. (e) Peng, T. S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174-4181.
159. (f) Agbossou, S. K.; Bodner, G. S.; Patton, A. T.; Gladysz, J. A. Organometallics 1990, 9, 1184-1191.
160. (g) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443-1444.