Chiral palladium(II)-bis(trichlorosilyl) complexes. Synthesis, structure, and combined QM/MM computational studies

Organometallics

Volumn 19, Issue 11, 2000, Pages 2144-2152

  Woo, Tom K ^a   Pioda, Giorgio ^a   Rothlisberger, Ursula ^a   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000530574     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000130g     Document Type: Article

References (74)

1. For reviews, see: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175-292. (b) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1998; Chapter 35. (c) Tilley, T. D. In The Chemistry of Organic Silicon Compounds Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Chapter 24. (d) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1991; pp 245-359. (e) Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363. For recent mechanistic and theoretical works on the hydrosilylation reaction, see: (f) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906. (g) Bosnich, B. Acc. Chem. Res. 1998, 31, 667. (h) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
2. For reviews, see: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175-292. (b) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1998; Chapter 35. (c) Tilley, T. D. In The Chemistry of Organic Silicon Compounds Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Chapter 24. (d) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1991; pp 245-359. (e) Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363. For recent mechanistic and theoretical works on the hydrosilylation reaction, see: (f) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906. (g) Bosnich, B. Acc. Chem. Res. 1998, 31, 667. (h) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
3. For reviews, see: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175-292. (b) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1998; Chapter 35. (c) Tilley, T. D. In The Chemistry of Organic Silicon Compounds Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Chapter 24. (d) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1991; pp 245-359. (e) Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363. For recent mechanistic and theoretical works on the hydrosilylation reaction, see: (f) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906. (g) Bosnich, B. Acc. Chem. Res. 1998, 31, 667. (h) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
4. For reviews, see: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175-292. (b) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1998; Chapter 35. (c) Tilley, T. D. In The Chemistry of Organic Silicon Compounds Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Chapter 24. (d) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1991; pp 245-359. (e) Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363. For recent mechanistic and theoretical works on the hydrosilylation reaction, see: (f) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906. (g) Bosnich, B. Acc. Chem. Res. 1998, 31, 667. (h) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
5. For reviews, see: (a) Corey, J. Y.; Braddock-Wilking, J. Chem. Rev. 1999, 99, 175-292. (b) Eisen, M. S. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1998; Chapter 35. (c) Tilley, T. D. In The Chemistry of Organic Silicon Compounds Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Chapter 24. (d) Tilley, T. D. In The Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1991; pp 245-359. (e) Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363. For recent mechanistic and theoretical works on the hydrosilylation reaction, see: (f) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906. (g) Bosnich, B. Acc. Chem. Res. 1998, 31, 667. (h) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510.
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40. The shorter M-Si bond lengths for electron-rich late transition metals have been attributed to M-Si π-back-bonding. See, e.g.: (a) Hübler, K.; Hunt, P.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 6883. (c) Koloski, T. S.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 489. (d) Lichtenberger, D. L.; Rai-Chaudhuri, A. Inorg. Chem. 1990, 29, 975. (e) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206. (f) Orpen, A. G. Chem. Soc. Rev. 1993, 191. (g) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653. It has also been pointed out that the more electronegative late transition-metals are able to polarize the M-Si bond, thus enhancing the electrostatic bond component shortening the bond. See: (g) Jiang, Q.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 3679.
41. The shorter M-Si bond lengths for electron-rich late transition metals have been attributed to M-Si π-back-bonding. See, e.g.: (a) Hübler, K.; Hunt, P.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 6883. (c) Koloski, T. S.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 489. (d) Lichtenberger, D. L.; Rai-Chaudhuri, A. Inorg. Chem. 1990, 29, 975. (e) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206. (f) Orpen, A. G. Chem. Soc. Rev. 1993, 191. (g) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653. It has also been pointed out that the more electronegative late transition-metals are able to polarize the M-Si bond, thus enhancing the electrostatic bond component shortening the bond. See: (g) Jiang, Q.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 3679.
42. The shorter M-Si bond lengths for electron-rich late transition metals have been attributed to M-Si π-back-bonding. See, e.g.: (a) Hübler, K.; Hunt, P.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 6883. (c) Koloski, T. S.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 489. (d) Lichtenberger, D. L.; Rai-Chaudhuri, A. Inorg. Chem. 1990, 29, 975. (e) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206. (f) Orpen, A. G. Chem. Soc. Rev. 1993, 191. (g) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653. It has also been pointed out that the more electronegative late transition-metals are able to polarize the M-Si bond, thus enhancing the electrostatic bond component shortening the bond. See: (g) Jiang, Q.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 3679.
43. The shorter M-Si bond lengths for electron-rich late transition metals have been attributed to M-Si π-back-bonding. See, e.g.: (a) Hübler, K.; Hunt, P.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 6883. (c) Koloski, T. S.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 489. (d) Lichtenberger, D. L.; Rai-Chaudhuri, A. Inorg. Chem. 1990, 29, 975. (e) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206. (f) Orpen, A. G. Chem. Soc. Rev. 1993, 191. (g) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653. It has also been pointed out that the more electronegative late transition-metals are able to polarize the M-Si bond, thus enhancing the electrostatic bond component shortening the bond. See: (g) Jiang, Q.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 3679.
44. The shorter M-Si bond lengths for electron-rich late transition metals have been attributed to M-Si π-back-bonding. See, e.g.: (a) Hübler, K.; Hunt, P.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 6883. (c) Koloski, T. S.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 489. (d) Lichtenberger, D. L.; Rai-Chaudhuri, A. Inorg. Chem. 1990, 29, 975. (e) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206. (f) Orpen, A. G. Chem. Soc. Rev. 1993, 191. (g) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653. It has also been pointed out that the more electronegative late transition-metals are able to polarize the M-Si bond, thus enhancing the electrostatic bond component shortening the bond. See: (g) Jiang, Q.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 3679.
45. The shorter M-Si bond lengths for electron-rich late transition metals have been attributed to M-Si π-back-bonding. See, e.g.: (a) Hübler, K.; Hunt, P.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 6883. (c) Koloski, T. S.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 489. (d) Lichtenberger, D. L.; Rai-Chaudhuri, A. Inorg. Chem. 1990, 29, 975. (e) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206. (f) Orpen, A. G. Chem. Soc. Rev. 1993, 191. (g) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653. It has also been pointed out that the more electronegative late transition-metals are able to polarize the M-Si bond, thus enhancing the electrostatic bond component shortening the bond. See: (g) Jiang, Q.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 3679.
46. The shorter M-Si bond lengths for electron-rich late transition metals have been attributed to M-Si π-back-bonding. See, e.g.: (a) Hübler, K.; Hunt, P.; Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Salter, D. M.; Schwerdtfeger, P.; Wright, L. J. Organometallics 1997, 16, 5076. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 6883. (c) Koloski, T. S.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 489. (d) Lichtenberger, D. L.; Rai-Chaudhuri, A. Inorg. Chem. 1990, 29, 975. (e) Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206. (f) Orpen, A. G. Chem. Soc. Rev. 1993, 191. (g) Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653. It has also been pointed out that the more electronegative late transition-metals are able to polarize the M-Si bond, thus enhancing the electrostatic bond component shortening the bond. See: (g) Jiang, Q.; Pestana, D. C.; Carroll, P. J.; Berry, D. H. Organometallics 1994, 13, 3679.
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49. See, e.g.: (a) Jagirdar, B. R.; Palmer, R.; Klabunde, K. J.; Radonovic, L. J. Inorg. Chem. 1995, 34, 278. (b) Robinson, W. T.; Ibers, J. A. Inorg. Chem. 1967, 6, 1208. (c) Yao, Z.; Klabunde, K. J.; Asirvatham, A. S. Inorg. Chem. 1995, 34, 5289. (d) Glavee, G. N.; Jagirdar, B. R.; Schneider, J. J.; Klabunde, K. J.; Radonovic, L. J.; Dodd, K. Organometallics 1992, 11, 1043. A Ni complex showing an opposite trend (longer Si-Cl bonds and larger Cl-Si-Cl angles) has been reported: Janikowski, S. K.; Radonovich, L. J.; Groeshens, T. J.; Klabunde, K. J. Organometallics 1985, 4, 396.
50. See, e.g.: (a) Jagirdar, B. R.; Palmer, R.; Klabunde, K. J.; Radonovic, L. J. Inorg. Chem. 1995, 34, 278. (b) Robinson, W. T.; Ibers, J. A. Inorg. Chem. 1967, 6, 1208. (c) Yao, Z.; Klabunde, K. J.; Asirvatham, A. S. Inorg. Chem. 1995, 34, 5289. (d) Glavee, G. N.; Jagirdar, B. R.; Schneider, J. J.; Klabunde, K. J.; Radonovic, L. J.; Dodd, K. Organometallics 1992, 11, 1043. A Ni complex showing an opposite trend (longer Si-Cl bonds and larger Cl-Si-Cl angles) has been reported: Janikowski, S. K.; Radonovich, L. J.; Groeshens, T. J.; Klabunde, K. J. Organometallics 1985, 4, 396.
51. See, e.g.: (a) Jagirdar, B. R.; Palmer, R.; Klabunde, K. J.; Radonovic, L. J. Inorg. Chem. 1995, 34, 278. (b) Robinson, W. T.; Ibers, J. A. Inorg. Chem. 1967, 6, 1208. (c) Yao, Z.; Klabunde, K. J.; Asirvatham, A. S. Inorg. Chem. 1995, 34, 5289. (d) Glavee, G. N.; Jagirdar, B. R.; Schneider, J. J.; Klabunde, K. J.; Radonovic, L. J.; Dodd, K. Organometallics 1992, 11, 1043. A Ni complex showing an opposite trend (longer Si-Cl bonds and larger Cl-Si-Cl angles) has been reported: Janikowski, S. K.; Radonovich, L. J.; Groeshens, T. J.; Klabunde, K. J. Organometallics 1985, 4, 396.
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73. For other reports concerning this aspect, see, e.g.: (a) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J Am. Chem. Soc. 1997, 119, 6177. (b) Cavallo, L.; Woo, T. K.; Ziegler, T. Can. J. Chem. 1998, 76, 1457. (c) Woo, T. K.; Ziegler, T. J. Organomet. Chem., in press. (d) Ujaque, G.; Maseras, F.; Lledós, A. J. Am. Chem. Soc. 1999, 121, 1317.
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