Poisoning of heterogeneous, late transition metal dehydrocoupling catalysts by boranes and other group 13 hydrides

Journal of the American Chemical Society

Volumn 127, Issue 14, 2005, Pages 5116-5124

  Jaska, Cory A ^a   Clark, Timothy J ^a   Clendenning, Scott B ^a   Grozea, Dan ^a   Turak, Ayse ^a   Lu, Zheng Hong ^a   Manners, Ian ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BORATE MINERALS; CATALYSIS; CATALYST POISONING; CATALYSTS; CHEMICAL BONDS; HYDRIDES; REDUCTION; RHODIUM COMPOUNDS; TRANSITION METALS;

BORANE REAGENTS; BORON-LAYERS; DEHYDROCOUPLING; HETEROGENEOUS CATALYSTS;

BORON COMPOUNDS;

ALUMINUM OXIDE; BORANE DERIVATIVE; CYCLOHEXENE; GALLIUM; HYDROGEN; PALLADIUM; REAGENT; REDUCING AGENT; RHODIUM; TETRAHYDROFURAN; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; COLLOID; DISSOCIATION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SUZUKI REACTION; SYNTHESIS;

EID: 17144373288     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0447412     Document Type: Article

References (119)

1. (a) Metal Nanoparticles: Synthesis, Characterization and Applications; Feldheim, D. L., Ed.; Dekker: New York, 2002.
2. (b) Nanoparticles: From Theory to Application; Schmid, G., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
3. (c) Nanoparticles: Building Blocks for Nanotechnology; Rotello, V. M., Ed.; Kluwer Academic/Plenum: New York, 2004.
4. Roucoux, A.; Schulz, J.; Patin, H. Chem. Rev. 2002, 102, 3757.
5. (a) Reetz, M. T.; Helbig, W. J. Am. Chem. Soc. 1994, 116, 7401.
6. (b) Reetz, M. T.; Quaiser, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2240.
7. See for example: (a) Lin, Y.; Finke, R. G. J. Am. Chem. Soc. 1994, 116, 8335.
8. (b) Bönnemann, H.; Brijoux, W.; Brinkmann, R.; Dinjus, E.; Joussen, T.; Korall, B. Angew. Chem., Int. Ed. Engl. 1991, 30, 1312.
9. (c) Raveendran, P.; Fu, J.; Wallen, S. L. J. Am. Chem. Soc. 2003, 125, 13940.
10. For representative examples, see the following. Polymer stabilized: (a) Chan, Y. N. C.; Schrock, R. R.; Cohen, R. E. J. Am. Chem. Soc. 1992, 114, 7295.
11. (b) Golden, J. H.; Deng, H.; DiSalvo, F. J.; Fréchet, J. M. J.; Thompson, P. M. Science 1995, 268, 1463.
12. (c) Watkins, J. J.; McCarthy, T. J. Chem. Mater. 1995, 7, 1991.
13. (d) Teranishi, T.; Hosoe, M.; Miyake, M. Adv. Mater. 1997, 9, 65.
14. Dendrimer stabilized: (e) Zhao, M.; Crooks, R. M. Angew. Chem., Int. Ed. 1999, 38, 364.
15. (f) Zhao, M.; Crooks, R. M. Adv. Mater. 1999, 11, 217.
16. Microgel stabilized: (g) Antonietti, M.; Gröhn, F.; Hartmann, J.; Bronstein, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 2080.
17. (h) Whilton, N. T.; Berton, B.; Bronstein, L.; Hentze, H. P.; Antonietti, M. Adv. Mater. 1999, 11, 1014.
18. (i) Biffis, A.; Orlandi, N.; Corain, B. Adv. Mater. 2003, 15, 1551.
19. For an example of using proteins to stabilize nanoclusters, see: Ueno, T.; Suzuki, M.; Goto, T.; Matsumoto, T.; Nagayama, K.; Watanabe, Y. Angew. Chem., Int. Ed. 2004, 43, 2527.
20. (a) Bönnemann, H.; Braun, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1992.
21. (b) Weddle, K. S.; Aiken, J. D., III; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 5653.
22. (c) Schulz, J.; Roucoux, A.; Patin, H. Chem. Eur. J. 2000, 6, 618.
23. (d) Dyson, P. J. Dalton Trans. 2003, 2964.
24. (e) Doyle, A. M.; Shaikhutdinov, S. K.; Jackson, S. D.; Freund, H.-J. Angew. Chem., Int. Ed. 2003, 42, 5240.
25. (a) Reetz, M. T.; Lohmer, G. Chem. Commun. 1996, 1921.
26. (b) Yeung, L. K.; Crooks, R. M. Nano Lett. 2001, 1, 14.
27. (c) Rahim, E. H.; Kamounah, F. S.; Frederiksen, J.; Christensen, J. B. Nano Lett. 2001, 1, 499.
28. (d) Caló, V.; Nacci, A.; Monopoli, A.; Detomaso, A.; Ilaide, P. Organometallics 2003, 22, 4193.
29. (e) Gopidas, K. R.; Whitesell, J. K.; Fox, M. A. Nano Lett. 2003, 3, 1757.
30. (f) Na, Y.; Park, S.; Han, S. B.; Han, H.; Ko, S.; Chang, S. J. Am. Chem. Soc. 2004, 126, 250.
31. Moreno-Mañas, M.; Pleixats, R. Acc. Chem. Res. 2003, 36, 638.
32. (a) Reetz, M. T.; Breinbaur, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
33. (b) Li, Y.; El-Sayed, M. A. J. Phys. Chem. B 2001, 105, 8938.
34. (c) Pittelkow, M.; Moth-Poulsen, K.; Boas, U.; Christensen, J. B. Langmuir 2003, 19, 7682.
35. (d) Biffis, A.; Sperotto, E. Langmuir 2003, 19, 9548.
36. (e) Narayanan, R.; El-Sayed, M. A. J. Am. Chem Soc. 2003, 125, 8340.
37. Son, S. U.; Park, I. K.; Park, J.; Hyeon, T. Chem. Commun. 2004, 778.
38. (a) Wu, X.; Neckers, D. C. Macromolecules 1999, 32, 6003.
39. (b) Temple, K.; Jäkle, F.; Sheridan, J. B.; Manners, I. J. Am. Chem. Soc. 2001, 123, 1355.
40. Chauhan, B. P. S.; Rathore, J. S.; Chauhan, M.; Krawicz, A. J. Am. Chem. Soc. 2003, 125, 2876.
41. Jansat, S.; Gómez, M.; Philippot, K.; Muller, G.; Guiu, E.; Claver, C.; Castillón, S.; Chaudret, B. J. Am. Chem. Soc. 2004, 126, 1592.
42. (a) Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855.
43. (b) Whitesides, G. M.; Hackett, M.; Brainard, R. L.; Lavalleye, J. P. P. M.; Sowinski, A. F.; Izumi, A. N.; Moore, S. S.; Brown, D. W.; Staudt, E. M. Organometallics 1985, 4, 1819.
44. Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 198, 317.
45. Hornstein, B. J.; Aiken, J. D., III; Finke, R. G. Inorg. Chem. 2002, 41, 1625.
46. A heterogeneous catalyst can be completely poisoned by < 1 equiv of ligand (per metal atom) because only a fraction of the metal atoms are on the surface, whereas a homogeneous catalyst would require > 1 equiv of ligand to completely poison the active site.
47. (a) Amiens, C.; de Caro, D.; Chaudret, B.; Bradley, J. S.; Mazel, R.; Roucau, C. J. Am. Chem. Soc. 1993, 115, 11638.
48. (b) de Caro, D.; Wally, H.; Amiens, C.; Chaudret, B. J. Chem. Soc., Chem. Commun. 1994, 1891.
49. (a) Duteil, A.; Schmid, G.; Meyer-Zaika, W. J. Chem. Soc., Chem. Commun. 1995, 31.
50. (b) Jiang, X.; Xie, Y.; Lu, J.; Zhu, L.; He, W.; Qian, Y. Langmuir 2001, 17, 3795.
51. The stability and catalytic activity of colloidal nanoparticles is anticorrelated: the most stable is the least catalytically active. See: Li, Y.; El-Sayed, M. A. J. Phys. Chem. B 2001, 105, 8938.
52. Jaska, C. A.; Bartole-Scott, A.; Manners, I. Dalton Trans. 2003, 4015.
53. (a) Dorn, H.; Singh, R. A.; Massey, J. A.; Lough, A. J.; Manners, I. Angew. Chem., Int. Ed. 1999, 38, 3321.
54. (b) Dorn, H.; Singh, R. A.; Massey, J. A.; Nelson, J. M.; Jaska, C. A.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2000, 122, 6669.
55. (c) Dorn, H.; Vejzovic, E.; Lough, A. J.; Manners, I. Inorg. Chem. 2001, 40, 4327.
56. (d) Dora, H.; Rodezno, J. M.; Brunnhöfer, B.; Rivard, E.; Massey, J. A.; Manners, I. Macromolecules 2003, 36, 291.
57. 3 catalyzed formation of P-B bonds via dehydrocoupling. see: Denis, J.-M.; Forintos, H.; Szelke, H.; Toupet, L.; Pham, T.-N.; Madec, P.-J.; Gaumont, A.-C. Chem. Commun. 2003, 54.
58. (a) Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. Chem. Commun. 2001, 962.
59. (b) Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2003, 125, 9424.
60. Jaska, C. A. Manners, I. J. Am. Chem. Soc. 2004, 126, 2698.
61. Jaska, C. A. Manners, I. J. Am. Chem. Soc. 2004, 126, 1334.
62. Jaska, C. A. Manners, I. J. Am. Chem. Soc. 2004, 126, 9776.
63. 3 on Rh colloids. For PPh3 on Pt and Cu colloids, Δδ values of ca. 51-56 and 34 ppm have been observed, respectively. See ref 19.
64. Tang, C. Y.; Coxall, R. A.; Downs, A. J.; Greene, T. M.; Kettle, L.; Parsons, S.; Rankin, D. W. H.; Robertson, H. E.; Turner, A. R. Dalton Trans. 2003, 3526.
65. Loschen, C.; Voigt, K.; Frunzke, J.; Diefenbach, A.; Diedenhofen, M.; Frenking, G. Z. Anorg. Allg. Chem. 2002, 628, 1294.
66. Haaland, A. Angew. Chem., Int. Ed. Engl. 1989, 28, 992.
67. -1, respectively. See: Rablen, P. R. J. Am. Chem. Soc. 1997, 119, 8350.
68. 1 complexes, see: (a) Shimoi, M.; Nagai, S. I.; Ichikawa, M.; Kawano, Y.; Katoh, K.; Uruichi, M.; Ogino, H. J. Am. Chem. Soc. 1999, 121, 11704.
69. (b) Kakizawa, T.; Kawano, Y.; Shimoi, M. Organometallics 2001, 20, 3211.
70. (c) Bajko, Z.; Daniels, J.; Gudat, D.; Häp, S.; Nieger, M. Organometallics 2002, 21, 5182.
71. 2 complexes, see: (d) Khan, K.; Raston, C. L.; McGrady, J. E.; Skelton, B. W.; White, A. H. Organometallics 1997, 16, 3252.
72. (e) Ingleson, M.; Patmore, N. J.; Ruggiero, G. D.; Frost, C. G.; Mahon, M. F.; Willis, M. C.; Weller, A. S. Organometallics 2001, 20, 4434.
73. (f) Volkov, O.; Macías, R.; Rath, N. P.; Barton, L. Inorg. Chem. 2002, 41, 5837.
74. 3 complexes, see: (g) White, J. P., III; Deng, H.; Shore, S. G. Inorg. Chem. 1991, 30, 2337.
75. (h) Gozum, J. E.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1992, 114, 9483.
76. For σ complexes, see: (i) Hartwig, J. F.; Muhoro, C. N.; He, X.; Eisenstein, O.; Bosque, R.; Maseras, F. J. Am. Chem. Soc. 1996, 118, 10936.
77. (j) Muhoro, C. N.; He, X.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 5033.
78. (k) Schlecht, S.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9435.
79. (a) Cowley, A. H.; Mills, J. L. J. Am. Chem. Soc. 1969, 91, 2911.
80. (b) Toyota, S.; Futawaka, T.; Asakura, M.; Ikeda, H.; Oki, M. Organometallics 1998, 17, 4155.
81. 2. Unpublished results.
82. 3 is formed as a byproduct, which is fully removed upon workup as indicated by the lack of a B(1s) peak in the XPS spectrum of the colloidal product. See Figure 2.
83. Böhm, V. P. W.; Brookhart, M. Angew. Chem., Int. Ed. 2001, 40, 4694.
84. Moulder, J. F.; Stickle, W. F.; Sobol, P. E.; Bomben, K. D. Handbook of X-ray Photoelectron Spectroscopy; Perkin-Elmer: Eden Prairie, MN, 1992.
85. Aronsson, B.; Aselius, J.; Stenberg, E. Nature 1959, 183, 1318.
86. Hoard, J. L.; Hughes, R. E. In The Chemistry of Boron and Its Compounds; Muetterties, E. L., Ed.; Wiley: New York, 1967; p 25.
87. Glavee, G. N.; Klabunde, K. J.; Sorensen, C. M.; Hadjipanayis, G. C. Inorg. Chem. 1993, 32, 474.
88. For examples involving reactions of B-H bonds at Rh centers, see; (a) Baker, R. T.; Ovenall, D. W.; Harlow, R. L.; Westcott, S. A.; Taylor, N. J.; Marder, T. B. Organometallics 1990, 9, 3028.
89. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350.
90. For a review on metal-boryl complexes see: (c) Braunschweig, H. Angew. Chem. Int. Ed. Engl. 1998, 37, 1786.
91. 3.
92. 2 in our laboratory have been unsuccessful to date, and thus the reactivity of this species with heterogeneous metal catalysts could not be investigated.
93. Shriver, D. F.; Parry, R. W.; Greenwood, N. N.; Storr, A.; Wallbridge, M. G. H. Inorg. Chem. 1963, 2, 867.
94. Greenwood, N. N. In New Pathways in Inorganic Chemistry; Ebsworth, E. A. V., Maddock, A. G., Sharpe, A. G., Eds.; Cambridge University Press: Cambridge, U.K., 1968; p 37.
95. (a) Bönnemann, H.; Brijoux, W.; Brinkmann, R.; Dinjus, E.; Joussen, T.; Korall, B. Angew. Chem., Int. Ed. Eng. 1991, 30, 1312.
96. (b) Bönnemann, H.; Braun, G.; Brijoux, W.; Brinkmann, R.; Schulze Tilling, A.; Seevogel, K.; Siepen, K. J. Organomet. Chem. 1996, 520, 143.
97. (c) Shulz, J.; Roucoux, A.; Patin, H. Chem. Eur. J. 2000, 6, 618.
98. (a) Mayer, A. B. R.; Mark, J. E. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 3151.
99. (b) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243.
100. (c) Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Nano Lett. 2002, 2, 999.
101. (d) Kidambi, S.; Dai, J.; Li, J.; Bruening, M. L. J. Am. Chem. Soc. 2004, 126, 2658.
102. 3·THF poisoned catalyst with a hydrogen atmosphere did not alter the reactivity of the catalyst; the catalyst was found to remain inactive toward dehydrocoupling. These two results indicate that substantial leaching of boron from the catalyst surface did not occur and that the surface coverage is incomplete, despite the poisoning of the sites responsible for dehydrocoupling. We thank a reviewer for suggesting these experiments.
103. (a) Li, Y.; Hong, X. M.; Collard, D. M.; El-Sayed, M. A. Org. Lett. 2000, 2, 2385.
104. (b) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529.
105. 3·-THF. Morrill, T. C.; D'Souza, C. A. Organometallics 2003, 22, 1626. However, to date, the exact nature of the active catalyst was not determined, and our results suggest that a homogeneous catalyst may need to be considered as the actual species responsible for the catalysis.
106. (a) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
107. (b) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.
108. (c) Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695.
109. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
110. Greenwood, N. N.; Ross, E. J. F.; Storr, A. J. Chem. Soc. 1965, 1400.
111. Ruff, J. K. Inorg. Synth. 1967, 9, 30.
112. Schmidbaur, H.; Weiss, E.; Müller, G. Synth. React. Inorg. Met.-Org. Chem. 1985, 15, 401.
113. Shriver, D. F.; Shirk, A. E. Inorg. Synth. 1977, 17, 42.
114. Keller, P. C. Synth. Inorg. Met.-Org. Chem. 1973, 3, 307.
115. Wideman, T.; Sneddon, L. G. Inorg. Chem. 1995, 34, 1002.
116. Narula, C. K.; Janik, J. F.; Duesler, E. N.; Paine, R. T.; Schaeffer, R. Inorg. Chem. 1986, 25, 3346.
117. Giordano, G.; Crabtree, R. H. Inorg. Synth. 1979, 19, 218.
118. Dodds, A. R.; Kodama, G. Inorg. Chem. 1979, 18, 1465.
119. Brown, H. C.; Ravindran, N. J. Am. Chem. Soc. 1976, 98, 1798.