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New Design in Homogeneous Palladium Catalysis: Study of Transformation of Group 14 Element Compounds and Development of Nanosize Palladium Catalysts

  • Tsuji, Yasushi (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University) ;
  • Fujihara, Tetsuaki (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University)
  • Published : 2007.11.20

Abstract

This account reports an overview of our findings in homogeneous Pd-catalyzed reactions. Herein we describe the new design in reactions of Group 14 element compounds and in homogeneous nanosize Pd catalysts. In the early stages of our study, we developed Pd-catalyzed transformations of allylic esters with disilanes, silylcyanides and acylsilanes to the corresponding silylation, cyanation and acylation products, respectively. We also developed a Pd-catalyzed three component coupling reaction of Group 14 element compounds involving 1,3-diene and acid chlorides to form β,γ-unsaturated ketone as a single product. Recently, we focus our attention on modifying the catalytic environment by nanosize Pd in order to improve the performance of Pd catalysts. These nanosystems realize efficient catalytic environment with remarkable enhancement in catalytic activity and unprecedented selectivity.

Keywords

References

  1. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002
  2. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds; Willy-VCH: Weinheim, 2004
  3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457 https://doi.org/10.1021/cr00039a007
  4. Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2001, 40, 4544 https://doi.org/10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N
  5. Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Willy-VCH: Weinheim, 2004; p 41
  6. Phan, N. T. S.; van der Sluys, M.; Jones, C. W. Adv. Synth. Cat. 2006, 348, 609 https://doi.org/10.1002/adsc.200505473
  7. Brase, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Willy-VCH: Weinheim, 2004; p 217
  8. Maes, B. U. W.; Tapolcsanyi, P.; Meyers, C.; Matyus, P. Curr. Org. Chem. 2006, 3, 377
  9. Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 4704
  10. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874 https://doi.org/10.1021/cr050992x
  11. Cornell, C. N.; Sigman, M. S. Inorg. Chem. 2007, 46, 1910 https://doi.org/10.1021/ic061997v
  12. Takacs, J. M.; Jiang, X.-T. Curr. Org. Chem. 2003, 7, 369 https://doi.org/10.2174/1385272033372851
  13. Stahl, S. S. Angew. Chem. Int. Ed. 2004, 43, 3400 https://doi.org/10.1002/anie.200300630
  14. Kotov, V.; Scarborough, C. C.; Stahl, S. S. Inorg. Chem. 2007, 46, 1910 https://doi.org/10.1021/ic061997v
  15. Deprez, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924 https://doi.org/10.1021/ic0620337
  16. Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221 https://doi.org/10.1021/ar040243m
  17. Nishimura, T.; Uemura, S. Synlett 2004, 201
  18. Stoltz, B. M. Chem. Lett. 2004, 33, 362 https://doi.org/10.1246/cl.2004.362
  19. Muzart, J. Tetrahedron 2003, 59, 5789 https://doi.org/10.1016/S0040-4020(03)00866-4
  20. Tsuji, Y.; Fujihara, T. Inorg. Chem. 2007, 46, 1895 https://doi.org/10.1021/ic061872q
  21. Tsuji, Y.; Obora, Y. Trends Organomet. Chem. 1999, 3, 165
  22. Tsuji, Y.; Funato, M.; Ozawa, M.; Ogiyama, H.; Kajita, S.; Kawamura, T. J. Org. Chem. 1996, 61, 5779 https://doi.org/10.1021/jo960345t
  23. Tsuji, Y.; Kajita, S.; Isobe, S.; Funato, M. J. Org. Chem. 1993, 58, 3607 https://doi.org/10.1021/jo00066a005
  24. Tsuji, Y.; Kusui, T.; Kojima, T.; Sugiura, Y.; Yamada, N.; Tanaka, S.; Ebihara, M.; Kawamura, T. Organometallics 1998, 17, 4835 https://doi.org/10.1021/om980511i
  25. Tsuji, Y.; Yamada, N.; Tanaka, S. J. Org. Chem. 1993, 58, 16 https://doi.org/10.1021/jo00053a007
  26. Tsuji, Y.; Taniguchi, M.; Yasuda, T.; Kawamura, T.; Obora, Y. Org. Lett. 2000, 2, 2635 https://doi.org/10.1021/ol006160x
  27. Obora, Y.; Ogawa, Y.; Imai, Y.; Kawamura, T.; Tsuji, Y. J. Am. Chem. Soc. 2001, 123, 10489 https://doi.org/10.1021/ja010674p
  28. Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S.; Rapport, Z., Eds.; Wiley: Chichester, 1989
  29. Obora, Y.; Nakanishi, M.; Tokunaga, M.; Tsuji, Y. J. Org. Chem. 2002, 67, 5835 https://doi.org/10.1021/jo0202482
  30. Terao, J.; Kambe, N. Chem. Rec. 2007, 7, 57 https://doi.org/10.1002/tcr.20101
  31. Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320 https://doi.org/10.1021/cr050530j
  32. Obora, Y.; Tsuji, Y.; Kawamura, T. J. Am. Chem. Soc. 1995, 117, 9814 https://doi.org/10.1021/ja00144a005
  33. Obora, Y.; Tsuji, Y.; Kawamura, T. J. Am. Chem. Soc. 1993, 115, 10414 https://doi.org/10.1021/ja00075a089
  34. Obora, Y.; Tsuji, Y.; Kobayashi, M.; Kawamura, T. J. Org. Chem. 1995, 60, 4647 https://doi.org/10.1021/jo00119a051
  35. Obora, Y.; Tsuji, Y.; Asayama, M.; Kawamura, T. Organometallics 1993, 12, 4697 https://doi.org/10.1021/om00035a069
  36. Tsuji, Y.; Kakehi, T. J. Chem. Soc., Chem. Commun. 1992, 1000
  37. Obora, Y.; Tsuji, Y.; Kakehi, T.; Kobayashi, M.; Shinkai, T.; Ebihara, M.; Kawamura, T. J. Chem. Soc., Perkin Trans. 1 1995, 599
  38. Obora, Y.; Tsuji, Y.; Kawamura, T. Organometallics 1993, 12, 2853 https://doi.org/10.1021/om00031a066
  39. Obora, Y.; Tsuji, Y.; Nishiyama, K.; Ebihara, M.; Kawamura, T. J. Am. Chem. Soc. 1996, 118, 10922 https://doi.org/10.1021/ja9626392
  40. Tsuji, Y.; Nishiyama, K.; Hori, S.; Ebihara, M.; Kawamura, T. Organometallics 1998, 17, 507 https://doi.org/10.1021/om970957j
  41. Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H., Ed.; Plenum: New York, 1983
  42. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Applications of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1999
  43. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principle and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, 1987; p 523
  44. Goto, K.; Ohzu, Y.; Sato, H.; Kawashima, T. 15th International Conference on Phosphorus Chemistry; Sendai, Japan, 2001, Abstr. No. PB072
  45. Goto, K.; Ohzu, Y.; Sato, H.; Kawashima, T. Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 2179 https://doi.org/10.1080/10426500213444
  46. Niyomura, O.; Tokunaga, M.; Obora, Y.; Iwasawa, T.; Tsuji, Y. Angew. Chem. Int. Ed. 2003, 42, 1287 https://doi.org/10.1002/anie.200390331
  47. Niyomura, O.; Iwasawa, T.; Sawada, N.; Tokunaga, M.; Obora, Y.; Tsuji, Y. Organometallics 2005, 24, 3468 https://doi.org/10.1021/om0503491
  48. Ohta, H.; Tokunaga, M.; Obora, Y.; Iwai, T.; Iwasawa, T.; Fujihara, T.; Tsuji, Y. Org. Lett. 2007, 9, 89 https://doi.org/10.1021/ol0626138
  49. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176 https://doi.org/10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
  50. Suresh, C. H.; Koga, N. Inorg. Chem. 2002, 41, 1573 https://doi.org/10.1021/ic0109400
  51. Allen, D. W.; Taylor, B. F. J. Chem. Soc. Dalton Trans. 1982, 51
  52. Socol, S. M.; Verkade, J. G. Inorg. Chem. 1984, 23, 3487 https://doi.org/10.1021/ic00190a011
  53. Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997 https://doi.org/10.1021/cr000024o
  54. Alyea, E. C.; Malito, J. Phosphorus, Sulfur, Silicon Relat. Elem. 1989, 46, 175
  55. Tolman, C. A. Chem. Rev. 1977, 77, 313 https://doi.org/10.1021/cr60307a002
  56. Newkome, G. R.; Moorefield, C. N.; Vogtle, F. Dendrimers and Dendrons: Concept, Synthesis, Application; Wiley-VHC: Veinheim, 2001
  57. Dendrimer and Other Dendritic Polymers; Frechet, J. M. J.; Tomalia, D. A., Eds.; Wiley & Sons: New York, 2001
  58. Dendrimer Catalysis; Top. Organomet. Chem.; Gade, L. H., Ed.; Springer: Heidelberg, 2006; Vol. 20
  59. de Schryver, F. C.; Vosch, T.; Cotlet, M.; van der Auweraer, M.; Mullen, K.; Hofkens, J. Acc. Chem. Res. 2005, 38, 514 https://doi.org/10.1021/ar040126r
  60. Watson, M. D.; Fechtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267 https://doi.org/10.1021/cr990322p
  61. Berresheim, A. J.; Muller, M.; Mullen, K. Chem. Rev. 1999, 99, 1747 https://doi.org/10.1021/cr970073+
  62. Iwasawa, T.; Komano, T.; Tajima, A.; Tokunaga, M.; Obora, Y.; Fujihara, T.; Tsuji, Y. Organometallics 2006, 25, 4665 https://doi.org/10.1021/om060615q
  63. Aoyama, H.; Tokunaga, M.; Kiyosu, J.; Iwasawa, T.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2005, 126, 10474
  64. Iwasawa, T.; Tokunaga, M.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2004, 126, 6554 https://doi.org/10.1021/ja031936l
  65. Maseras, F.; Morokuma, K. J. Comp. Chem. 1995, 16, 1170 https://doi.org/10.1002/jcc.540160911
  66. Humbel, S.; Sieber, S.; Morokuma, K. J. Chem. Phys. 1996, 105, 1959 https://doi.org/10.1063/1.472065
  67. Svensson, M.; Humbel, S.; Froese, R. D. J.; Matsubara, T.; Sieber, S.; Morokuma, K. J. Phys. Chem. 1996, 100, 19357 https://doi.org/10.1021/jp962071j
  68. Kravtsova, S. V.; Romm, I. P.; Stash, A. I.; Belsky, V. K. Acta. Crystallogr. Sect. C 1996, C52, 2201
  69. Komano, T.; Iwasawa, T.; Tokunaga, M.; Obora, Y.; Tsuji, Y. Org. Lett. 2005, 7, 4677 https://doi.org/10.1021/ol051845o
  70. Sato, H.; Fujihara, T.; Obora, Y.; Tokunaga, M.; Kiyosu, J.; Tsuji, Y. Chem. Commn. 2007, 269
  71. Fujihara, T.; Obora, Y.; Tokunaga, M.; Sato, H.; Tsuji, Y. Chem. Commn. 2005, 4526
  72. Fujihara, T.: Obora, Y.; Tokunaga, M.; Tsuji, Y. Dalton Trans. 2007, 1567
  73. Takenaka, K.; Obora, Y.; Jiang, L. H.; Tsuji, Y. Organometallics 2002, 21, 1158 https://doi.org/10.1021/om010882q
  74. Takenaka, K.; Obora, Y.; Jiang, L. H.; Tsuji, Y. Bull. Chem. Soc. Jpn. 2001, 74, 1709 https://doi.org/10.1246/bcsj.74.1709
  75. Takenaka, K.; Obora, Y.; Tsuji, Y. Inorg. Chim. Acta 2004, 357, 3895 https://doi.org/10.1016/j.ica.2004.03.037
  76. Obora, Y.; Liu, Y. K.; Jiang, L. H.; Takenaka, K.; Tokunaga, M.; Tsuji, Y. Organometallics 2005, 24, 4 https://doi.org/10.1021/om049227j
  77. Oora, Y.; Liu, Y. K.; Kubouchi, S.; Tokunaga, M.; Tsuji, Y. Eur. J. Inorg. Chem. 2006, 222

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