Transition metal-catalyzed formation of boron-nitrogen bonds: Catalytic dehydrocoupling of amine-borane adducts to form aminoboranes and borazines

Journal of the American Chemical Society

Volumn 125, Issue 31, 2003, Pages 9424-9434

  Jaska, Cory A ^a   Temple, Karen ^a,b   Lough, Alan J ^a   Manners, Ian ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b IBM T J WATSON RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON COMPOUNDS; CATALYST ACTIVITY; CHEMICAL BONDS; MONOMERS;

DEHYDROCOUPLINGS;

AMINES;

AMINE; AMINOBORANE DERIVATIVE; BORANE DERIVATIVE; BORAZINE DERIVATIVE; BORON; IRIDIUM COMPLEX; LEAD; METAL COMPLEX; NITROGEN; PALLADIUM COMPLEX; RUTHENIUM COMPLEX; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; COLLOID; DEHYDROCOUPLING; MERCURIALISM; REACTION TIME; SYNTHESIS; TEMPERATURE; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0041707915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030160l     Document Type: Article

References (88)

1. For some recent examples, see: (i) Atom Transfer Radical Polymerization (ATRP): (a) Matyjaszewski, K. Curr. Org. Chem. 2002, 6, 67. (ii) Olefin Metathesis reactions such as Ring Opening Metathesis Polymerization (ROMP) and Ring Closing Metathesis (RCM): (b) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565. (c) Fürstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012. (iii) Cross-coupling reactions: (d) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187. (e) Metal Catalyzed Cross-Coupling Reactions, Diederich, F.; Stang, P. J. Eds., Wiley-VCH: New York, 1998. (iv) Asymmetric synthesis: (f) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Wiley: New York, 1994.
2. For some recent examples, see: (i) Atom Transfer Radical Polymerization (ATRP): (a) Matyjaszewski, K. Curr. Org. Chem. 2002, 6, 67. (ii) Olefin Metathesis reactions such as Ring Opening Metathesis Polymerization (ROMP) and Ring Closing Metathesis (RCM): (b) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565. (c) Fürstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012. (iii) Cross-coupling reactions: (d) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187. (e) Metal Catalyzed Cross-Coupling Reactions, Diederich, F.; Stang, P. J. Eds., Wiley-VCH: New York, 1998. (iv) Asymmetric synthesis: (f) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Wiley: New York, 1994.
3. For some recent examples, see: (i) Atom Transfer Radical Polymerization (ATRP): (a) Matyjaszewski, K. Curr. Org. Chem. 2002, 6, 67. (ii) Olefin Metathesis reactions such as Ring Opening Metathesis Polymerization (ROMP) and Ring Closing Metathesis (RCM): (b) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565. (c) Fürstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012. (iii) Cross-coupling reactions: (d) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187. (e) Metal Catalyzed Cross-Coupling Reactions, Diederich, F.; Stang, P. J. Eds., Wiley-VCH: New York, 1998. (iv) Asymmetric synthesis: (f) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Wiley: New York, 1994.
4. For some recent examples, see: (i) Atom Transfer Radical Polymerization (ATRP): (a) Matyjaszewski, K. Curr. Org. Chem. 2002, 6, 67. (ii) Olefin Metathesis reactions such as Ring Opening Metathesis Polymerization (ROMP) and Ring Closing Metathesis (RCM): (b) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565. (c) Fürstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012. (iii) Cross-coupling reactions: (d) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187. (e) Metal Catalyzed Cross-Coupling Reactions, Diederich, F.; Stang, P. J. Eds., Wiley-VCH: New York, 1998. (iv) Asymmetric synthesis: (f) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Wiley: New York, 1994.
5. For some recent examples, see: (i) Atom Transfer Radical Polymerization (ATRP): (a) Matyjaszewski, K. Curr. Org. Chem. 2002, 6, 67. (ii) Olefin Metathesis reactions such as Ring Opening Metathesis Polymerization (ROMP) and Ring Closing Metathesis (RCM): (b) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565. (c) Fürstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012. (iii) Cross-coupling reactions: (d) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187. (e) Metal Catalyzed Cross-Coupling Reactions, Diederich, F.; Stang, P. J. Eds., Wiley-VCH: New York, 1998. (iv) Asymmetric synthesis: (f) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Wiley: New York, 1994.
6. For some recent examples, see: (i) Atom Transfer Radical Polymerization (ATRP): (a) Matyjaszewski, K. Curr. Org. Chem. 2002, 6, 67. (ii) Olefin Metathesis reactions such as Ring Opening Metathesis Polymerization (ROMP) and Ring Closing Metathesis (RCM): (b) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565. (c) Fürstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012. (iii) Cross-coupling reactions: (d) Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187. (e) Metal Catalyzed Cross-Coupling Reactions, Diederich, F.; Stang, P. J. Eds., Wiley-VCH: New York, 1998. (iv) Asymmetric synthesis: (f) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Wiley: New York, 1994.
7. Aitken, C. T.; Harrod, J. F.; Samuel, E. J. Am. Chem. Soc. 1986, 108, 4059.
8. Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363.
9. For metal-catalyzed routes to transition metal-containing polymers, see for example: (a) Steffen, W.; Köhler, B.; Altmann, M.; Scherf, U.; Stitzer, K.; zur Loye, H.-C.; Bunz, U. H. F. Chem. Eur. J. 2001, 7, 117. (b) Gómez-Elipe, P.; Resendes, R.; Macdonald, P. M.; Manners, I. J. Am. Chem. Soc. 1998, 120, 8348. (c) Knapp, R.; Velten, U.; Rehahn, M. Polymer 1998, 39, 5827. (d) Kelch, S.; Rehahn, M. Macromolecules 1997, 30, 6185.
10. For metal-catalyzed routes to transition metal-containing polymers, see for example: (a) Steffen, W.; Köhler, B.; Altmann, M.; Scherf, U.; Stitzer, K.; zur Loye, H.-C.; Bunz, U. H. F. Chem. Eur. J. 2001, 7, 117. (b) Gómez-Elipe, P.; Resendes, R.; Macdonald, P. M.; Manners, I. J. Am. Chem. Soc. 1998, 120, 8348. (c) Knapp, R.; Velten, U.; Rehahn, M. Polymer 1998, 39, 5827. (d) Kelch, S.; Rehahn, M. Macromolecules 1997, 30, 6185.
11. For metal-catalyzed routes to transition metal-containing polymers, see for example: (a) Steffen, W.; Köhler, B.; Altmann, M.; Scherf, U.; Stitzer, K.; zur Loye, H.-C.; Bunz, U. H. F. Chem. Eur. J. 2001, 7, 117. (b) Gómez-Elipe, P.; Resendes, R.; Macdonald, P. M.; Manners, I. J. Am. Chem. Soc. 1998, 120, 8348. (c) Knapp, R.; Velten, U.; Rehahn, M. Polymer 1998, 39, 5827. (d) Kelch, S.; Rehahn, M. Macromolecules 1997, 30, 6185.
12. For metal-catalyzed routes to transition metal-containing polymers, see for example: (a) Steffen, W.; Köhler, B.; Altmann, M.; Scherf, U.; Stitzer, K.; zur Loye, H.-C.; Bunz, U. H. F. Chem. Eur. J. 2001, 7, 117. (b) Gómez-Elipe, P.; Resendes, R.; Macdonald, P. M.; Manners, I. J. Am. Chem. Soc. 1998, 120, 8348. (c) Knapp, R.; Velten, U.; Rehahn, M. Polymer 1998, 39, 5827. (d) Kelch, S.; Rehahn, M. Macromolecules 1997, 30, 6185.
13. (a) Aitken, C.; Harrod, J. F.; Malek, A.; Samuel, E. J. Organomet. Chem. 1988, 349, 285.
14. (b) Choi, N.; Tanaka, M. J. Organomet. Chem. 1998, 564, 81.
15. (c) For the formation of Ge-Ge bonds via Ru-catalyzed demethanative coupling, see: Katz, S. M.; Reichl, J. A.; Berry, D. H. J. Am. Chem. Soc. 1998, 120, 9844.
16. (a) Imori, T.; Tilley, T. D. J. Chem. Soc., Chem. Commun. 1993, 1607.
17. (b) Imori, T.; Lu, V.; Cai, H.; Tilley, T. D. J. Am. Chem. Soc. 1995, 117, 9931.
18. (c) Babcock, J. R.; Sita, L. R. J. Am. Chem. Soc. 1996, 118, 12481.
19. (a) Etkin, N.; Fermin, M. C.; Stephan, D. W. J. Am. Chem. Soc. 1997. 119, 2954.
20. (b) Hoskin, A. J.; Stephan, D. W. Angew. Chem., Int. Ed. Engl. 2001, 40, 1865.
21. (c) Böhm, V. P. W.; Brookhart, M. Angew. Chem., Int. Ed. Engl. 2001, 40, 4694.
22. Jiang, Q.; Carroll, P. J.; Berry, D. H. Organometallics 1993, 12, 177.
23. Coapes, R. B.; Souza, F. E. S.; Thomas, R. L.; Hall, J. J.; Marder, T. B. Chem. Commun. 2003, 614.
24. (a) Procopio, L. J.; Berry, D. H. J. Am. Chem. Soc. 1991, 113, 4039.
25. (b) Sadow, A. D.; Tilley, T. D. Angew. Chem., Int. Ed. Engl. 2003, 42, 803.
26. Fischer, J. M.; Piers, W. E.; Pearce Batchilder, S. D.; Zaworotko, M. J. J. Am. Chem. Soc. 1996, 118, 283.
27. Shu, R.; Hao, L.; Harrod, J. F.; Woo, H. G.; Samuel, E. J. Am. Chem. Soc. 1998, 120, 12 988.
28. He, J.; Lui, H. Q.; Harrod, J. F.; Hynes, R. Organometallics 1994, 13, 336.
29. (a) Li, Y.; Kawakami, Y. Macromolecules 1999, 32, 6871.
30. (b) Zhang, R.; Mark, J. E.; Pinhas, A. R. Macromolecules 2000, 33, 3508.
31. (c) Ready, T. E.; Chauhan, B. P. S.; Boudjouk, P. Macromol. Rapid Commun. 2001, 22, 654.
32. (a) Dorn, H.; Singh, R. A.; Massey, J. A.; Lough, A. J.; Manners, I. Angew. Chem., Int. Ed. Engl. 1999, 38, 3321.
33. (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.
34. (c) Dorn, H.; Jaska, C.A.; Singh, R. A.; Lough, A. J.; Manners, I. Chem. Commun. 2000, 1041.
35. (d) Dorn, H.; Rodezno, J. M.; Brunnhöffer, B.; Rivard, E.; Massey, J. A.; Manners, I. Macromolecules 2003, 36, 291.
36. (e) Jaska, C. A.; Dorn, H.; Lough, A. J.; Manners, I. Chem. Eur. J. 2003, 9, 271.
37. 3 was synthesized in 1809: Gay-Lussac, J. L.; Thenard, J. L. Mem. Phys. Chim. Soc. d'Arcueil 1809, 2, 210.
38. Niedenzu, K.; Dawson, J. W. Boron-Nitrogen Compounds; Academic Press Inc.: New York, 1965.
39. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
40. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
41. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
42. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
43. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
44. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
45. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
46. n, which are insoluble: (c) Paetzold, P.; von Bennigsen-Mackiewicz, T. Chem. Ber. 1981, 114, 298. (d) Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123. In addition, polymers containing B-N linkages as part of the main chain are also known: (e) Grosche, M.; Herdtweck, E.; Peters, F.; Wagner, M. Organometallics 1999, 18, 4669. (f) Matsumi, N.; Chujo, Y. Macromolecules 1998, 31, 3802. (g) Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403. Chujo, Y.; Tomita, I.; Murata, N.; Mauermann, H.; Saegusa, T. Macromolecules 1992, 25, 27.
47. Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. Chem. Commun. 2001, 962.
48. 12 as a catalyst. Blum, Y. D.; Laine, R. M. US Pat. 4801439, 1989.
49. 12 as a catalyst. Blum, Y. D.; Laine, R. M. US Pat. 4801439, 1989.
50. 12 as a catalyst. Blum, Y. D.; Laine, R. M. US Pat. 4801439, 1989.
51. Burg, A. B.; Randolph, Jr., C. L. J. Am. Chem. Soc. 1949, 71, 3451.
52. n which are not well-characterized. See ref 18c and 18d. (iii) The first addition polymerization of an inorganic multiply bonded monomer to give a soluble, well-characterized polymeric product has been reported recently. See: (c) Tsang, C.-W.; Yam, M.; Gates, D. P. J. Am. Chem. Soc. 2003, 125, 1480.
53. n which are not well-characterized. See ref 18c and 18d. (iii) The first addition polymerization of an inorganic multiply bonded monomer to give a soluble, well-characterized polymeric product has been reported recently. See: (c) Tsang, C.-W.; Yam, M.; Gates, D. P. J. Am. Chem. Soc. 2003, 125, 1480.
54. n which are not well-characterized. See ref 18c and 18d. (iii) The first addition polymerization of an inorganic multiply bonded monomer to give a soluble, well-characterized polymeric product has been reported recently. See: (c) Tsang, C.-W.; Yam, M.; Gates, D. P. J. Am. Chem. Soc. 2003, 125, 1480.
55. 3 is an intermolecular process: Ryschkewitsch, G. E.; Wiggins, J. W. Inorg. Chem. 1970, 9, 314.
56. Denis, J.-M.; Forintos, H.; Szelke, H.; Toupet, L.; Pham, T.-N.; Madec, P.-J.; Gaumont, A. C. Chem. Commun. 2003, 54.
57. Trefonas, L. M.; Lipscomb, W. N. J. Am. Chem. Soc. 1959, 81, 4435.
58. Kanjolia, R. K.; Krannich, L. K.; Watkins, C. L. J. Chem. Soc., Dalton Trans. 1986, 2345,
59. Nöth, H.; Vahrenkamp, H. Chem. Ber. 1967, 100, 3353.
60. 2 proceeds by the linear dimer intermediate 5. See ref 23 and also Beachley Jr., O. T. Inorg. Chem. 1967, 6, 870.
61. Nöth, H.; Thomas, S. Eur. J. Inorg. Chem. 1999, 1373.
62. Klooster, W. T.; Koetzle, T. F.; Siegbahn, P. E. M.; Richardson, T. B.; Crabtree, R. H. J. Am. Chem. Soc. 1999. 121, 6337.
63. 2NH.
64. Gaines, D. F.; Schaeffer, R. J. Am. Chem. Soc. 1963, 85, 3592.
65. Gaines, D. F.; Schaeffer, R. J. Am. Chem. Soc. 1964, 86, 1505.
66. Wang, J. S.; Geanangel, R. A. Inorg. Chim. Acta 1988, 148, 185.
67. For an example of the trap-to-trap vacuum fractionation setup for product purification, see: Wideman, T.; Fazen, P. J.; Lynch, A. T.; Su, K.; Remsen, E. E.; Sneddon, L. G. Inorg. Synth. 1998, 32, 232.
68. Narula, C. K.; Janik, J. F.; Duesler, E. N.; Paine, R. T.; Schaeffer, R. Inorg. Chem. 1986, 25, 3346.
69. Bissot, T. C.; Parry, R. W. J. Am. Chem. Soc. 1955, 77, 3481.
70. Lux, D.; Schwarz, W.; Hess, H. Crystal. Struct. Commun. 1979, 8, 33.
71. (a) Stein, J.; Lewis, L. N.; Gao, Y.; Scott, R. A. J. Am. Chem. Soc. 1999, 121, 3693.
72. (b) Weddle, K. S.; Aiken III, J. D.; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 5653.
73. For previous examples of Hg poisoning of heterogeneous Rh catalysts, see: (a) Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855. (b) Young Jr., R. J.; Grushin, V. V. Organometallics 1999, 18, 294. (c) See ref 39b.
74. For previous examples of Hg poisoning of heterogeneous Rh catalysts, see: (a) Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855. (b) Young Jr., R. J.; Grushin, V. V. Organometallics 1999, 18, 294. (c) See ref 39b.
75. For previous examples of Hg poisoning of heterogeneous Rh catalysts, see: (a) Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855. (b) Young Jr., R. J.; Grushin, V. V. Organometallics 1999, 18, 294. (c) See ref 39b.
76. (a) Wideman, T.; Sneddon, L. G. Chem. Mater. 1996, 8, 3.
77. (b) Toury, B.; Miele, P.; Cornu, D.; Vincent, H.; Bouix, J. Adv. Funct. Mater. 2002, 12, 228.
78. Lourie, O. R.; Jones, C. R.; Bartlett, B. M.; Gibbons, P. C.; Ruoff, R. S.; Buhro, W. E. Chem. Mater. 2000, 12, 1808.
79. (a) Hahn, G. A.; Schaeffer, R. J. Am. Chem. Soc. 1964, 86, 1503.
80. (b) Keller, P. C. Synth. Inorg. Met-Org. Chem. 1973, 3, 307.
81. Giordano, G.; Crabtree, R. H. Inorg. Synth. 1979, 19, 218.
82. Herde, J. L.; Lambert, J. C.; Senoff, C. V. Inorg. Synth. 1974, 15, 18.
83. Petasis, N. A. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester; 1995, p 470.
84. White, C.; Yates, A.; Maitlis, P. M. Inorg. Synth. 1992, 29, 228.
85. Statler, J. A.; Wilkinson, G.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1984, 1731.
86. Green, M.; Kuc, T. A.; Taylor, S. H. J. Chem. Soc. 1971, 2334.
87. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
88. Sheldrick, G. M. SHELXTL-PC V5.1; Bruker Analytical X-ray Systems Inc.: Madison, WI, 1997.