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Cascade and Sequential Catalytic Transformations Initiated by Ruthenium Catalysts

  • Christian BruneauEmail author
  • Sylvie Dérien
  • Pierre H. Dixneuf
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 19)

Abstract

Ruthenium holds a prominent position among the efficient transition metals involved in catalytic processes. Molecular ruthenium catalysts are able to perform unique transformations based on a variety of reaction mechanisms. They arise from easy to make complexes with versatile catalytic properties, and are ideal precursors for the performance of successive chemical transformations and catalytic reactions. This review provides examples of catalytic cascade reactions and sequential transformations initiated by ruthenium precursors present from the outset of the reaction and involving a common mechanism, such as in alkene metathesis, or in which the compound formed during the first step is used as a substrate for the second ruthenium-catalyzed reaction. Multi-metallic sequential catalytic transformations promoted by ruthenium complexes first, and then by another metal precursor will also be illustrated.

Cascade catalytic reactions Ruthenium catalysis Sequential catalytic reactions 

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References

  1. 1.
    Bruneau C, Dixneuf PH (2004) Topics in Organometallic Chemistry, vol 11. Ruthenium Catalysts and Fine Chemistry. Springer, Berlin, Heidelberg, New York, p 336 Google Scholar
  2. 2.
    Murahashi S-I (2004) Ruthenium in Organic Synthesis. Wiley, New York, p 398 Google Scholar
  3. 3.
    Fogg DE, dos Santos EN (2004) Coord Chem Rev 248:2365 CrossRefGoogle Scholar
  4. 4.
    Mori M (1998) Top Organomet Chem 1:133 CrossRefGoogle Scholar
  5. 5.
    Connon J, Blechert S (2004) Top Organomet Chem 11:93 Google Scholar
  6. 6.
    Diver ST, Giessert AJ (2004) Chem Rev 104:1317 CrossRefGoogle Scholar
  7. 7.
    Kim S-H, Bowden N, Grubbs RH (1994) J Am Chem Soc 116:10801 CrossRefGoogle Scholar
  8. 8.
    Kim S-H, Zuercher WJ, Bowden N, Grubbs RH (1196) J Org Chem 61:1073 CrossRefGoogle Scholar
  9. 9.
    Zuercher WJ, Scholl M, Grubbs R (1998) J Org Chem 63:4291 CrossRefGoogle Scholar
  10. 10.
    Choi T-L, Grubbs RH (2001) Chem Commun, p 2648 Google Scholar
  11. 11.
    Huang J, Xiong H, Hsung RP, Rameshkumar C, Mulder JA, Grebe TP (2002) Org Lett 4:2417 CrossRefGoogle Scholar
  12. 12.
    Boyer F-D, Hanna I, Ricard L (2001) Org Lett 3:3095 CrossRefGoogle Scholar
  13. 13.
    Wu C-J, Madhushaw RJ, Liu R-S (2003) J Org Chem 68:7889 CrossRefGoogle Scholar
  14. 14.
    Codesido EM, Castedo L, Granja JR (2001) Org Lett 3:1483 CrossRefGoogle Scholar
  15. 15.
    Boyer F-D, Hanna I (2002) Tetrahedron Lett 43:7469 CrossRefGoogle Scholar
  16. 16.
    Peppers BP, Diver ST (2004) J Am Chem Soc 126:9524 CrossRefGoogle Scholar
  17. 17.
    Kitamura T, Mori M (2001) Org Lett 3:1161 CrossRefGoogle Scholar
  18. 18.
    Rückert A, Eisele D, Blechert S (2001) Tetrahedron Lett 42:5245 CrossRefGoogle Scholar
  19. 19.
    Randl S, Lucas N, Connon SJ, Blechert S (2002) Adv Synth Catal 344:631 CrossRefGoogle Scholar
  20. 20.
    Arjona O, Csákÿ AG, Murcia MC, Plumet J (2000) Tetrahedron Lett 41:9777 CrossRefGoogle Scholar
  21. 21.
    Imhof S, Blechert S (2003) Synlett, p 609 Google Scholar
  22. 22.
    Mori M, Kuzuba Y, Kitamura T, Sato Y (2002) Org Lett 4:3855 CrossRefGoogle Scholar
  23. 23.
    Royer F, Vilain C, Elkaïn L, Grimaud L (2003) Org Lett 5:2007 CrossRefGoogle Scholar
  24. 24.
    Park S, Kim M, Lee D (2005) J Am Chem Soc 127:9410–9415 CrossRefGoogle Scholar
  25. 25.
    Smulik JA, Diver ST (2001) Tetrahedron Lett 42:171 CrossRefGoogle Scholar
  26. 26.
    Kulkarni AA, Diver St (2003) Org Lett 5:3463 CrossRefGoogle Scholar
  27. 27.
    Stragies R, Schuster M, Blechert S (1999) Chem Commun, p 237 Google Scholar
  28. 28.
    Banti D, North M (2002) Adv Synth Catal 344:694 CrossRefGoogle Scholar
  29. 29.
    Zuercher WJ, Hashimoto M, Grubbs R (1996) J Am Chem Soc 118:6634 CrossRefGoogle Scholar
  30. 30.
    Stragies R, Blechert S (1999) Tetrahedron 55:8179 CrossRefGoogle Scholar
  31. 31.
    Stapper C, Blechert S (2002) J Org Chem 67:6456 CrossRefGoogle Scholar
  32. 32.
    Blechert S, Stapper C (2002) Eur J Org Chem, p 2855 Google Scholar
  33. 33.
    Zaminer J, Stapper C, Blechert S (2002) Tetrahedron Lett 43:6739 CrossRefGoogle Scholar
  34. 34.
    Schaudt M, Blechert S (2003) J Org Chem 68:2913 CrossRefGoogle Scholar
  35. 35.
    Voigtmann U, Blechert S (2000) Synthesis, p 893 Google Scholar
  36. 36.
    Stragies R, Blechert S (2000) J Am Chem Soc 122:9584 CrossRefGoogle Scholar
  37. 37.
    Voigtmann U, Blechert S (2000) Org Lett 2:3971 CrossRefGoogle Scholar
  38. 38.
    Buschmann N, Rückert A, Blechert S (2002) J Org Chem 67:4325 CrossRefGoogle Scholar
  39. 39.
    Wrobleski A, Sahasrabudhe K, Aubé J (2002) J Am Chem Soc 124:9974 CrossRefGoogle Scholar
  40. 40.
    Stragies R, Blechert S (1998) Synlett, p 169 Google Scholar
  41. 41.
    Arjona O, Csákÿ AG, Medel R, Plumet J (2002) J Org Chem 67:1380 CrossRefGoogle Scholar
  42. 42.
    Bassindale MJ, Hamley P, Leitner A, Harrity JPA (1999) Tetrahedron Lett 40:3247 CrossRefGoogle Scholar
  43. 43.
    Bassindale MJ, Edwards AS, Hamley P, Adams H, Harrity JPA (2000) Chem Commun, p 1035 Google Scholar
  44. 44.
    Grushin VV, Alper H (1991) J Org Chem 56:5159 CrossRefGoogle Scholar
  45. 45.
    Mitsudo T, Suzuki N, Kobayashi T, Kondo T (1999) J Mol Catal A: Chem 137:253 CrossRefGoogle Scholar
  46. 46.
    Fürstner A, Thiel OR, Ackermann L, Schanz HJ, Nolan SP (2000) J Org Chem 65:2204 CrossRefGoogle Scholar
  47. 47.
    Kinderman SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Rutjes FPJT (2001) Org Lett 3:2045 CrossRefGoogle Scholar
  48. 48.
    van Otterlo WAL, Ngidi EL, de Koning CB (2003) Tetrahedron Lett 44:6483 CrossRefGoogle Scholar
  49. 49.
    Arisawa M, Terada Y, Nakagawa M, Nishida A (2002) Angew Chem Int Ed 41:4732 CrossRefGoogle Scholar
  50. 50.
    Sutton AE, Seigal BA, Finnegan DF, Snapper ML (2002) J Am Chem Soc 124:13390 CrossRefGoogle Scholar
  51. 51.
    Sémeril D, Cléran M, Jimenez Perez A, Bruneau C, Dixneuf PH (2002) J Mol Catal A: Chem 190:9 CrossRefGoogle Scholar
  52. 52.
    Yao Q (2001) Org Lett 3:2069 CrossRefGoogle Scholar
  53. 53.
    Schürer SC, Blechert S (1999) Tetrahedron Lett 40:1877 CrossRefGoogle Scholar
  54. 54.
    Kotha S, Sreenivasachary N, Brahmachary E (1998) Tetrahedron Lett 39:2805 CrossRefGoogle Scholar
  55. 55.
    Sémeril D, Le Nôtre J, Bruneau C, Dixneuf PH, Kolomiets AF, Osipov SN (2001) New J Chem 25:16 CrossRefGoogle Scholar
  56. 56.
    Ackermann L, Bruneau C, Dixneuf PH (2001) Synlett, p 397 Google Scholar
  57. 57.
    Sémeril D, Cléran M, Bruneau C, Dixneuf PH (2001) Adv Synth Catal 343:184 CrossRefGoogle Scholar
  58. 58.
    Heerding DA, Takata DT, Kwon C, Huffman WF, Samanen J (1998) Tetrahedron Lett 39:6815 CrossRefGoogle Scholar
  59. 59.
    Yang YK, Tae J (2003) Synlett, p 2017 Google Scholar
  60. 60.
    Rosillo M, Dominguez G, Casarrubios L, Amador U, Perez-Castells J (2004) J Org Chem 69:2084 CrossRefGoogle Scholar
  61. 61.
    Schmidt B (2004) Synlett, p 1541 Google Scholar
  62. 62.
    Le Nôtre J, Brissieux L, Sémeril D, Bruneau C, Dixneuf PH (2002) Chem Commun, p 1772 Google Scholar
  63. 63.
    Ben Ammar H, Le Nôtre J, Salem M, Kaddachi MT, Toupet L, Renaud JL, Bruneau C, Dixneuf PH (2003) Eur J Inorg Chem, p 4055 Google Scholar
  64. 64.
    Le Nôtre J, Touzani R, Lavastre O, Bruneau C, Dixneuf PH (2005) Adv Synth Catal 347:783 CrossRefGoogle Scholar
  65. 65.
    Gemel C, Trimmel G, Slugovc C, Kremel S, Mereiter K, Schmid R, Kirchner K (1996) Organometallics 15:3998 CrossRefGoogle Scholar
  66. 66.
    Reuter JM, Salomon RG (1977) J Org Chem 42:3360 CrossRefGoogle Scholar
  67. 67.
    Eilbracht P, Gersmeier A, Lennartz D, Huber T (1995) Synthesis, p 330 Google Scholar
  68. 68.
    Özdemir I, Cetinkaya E, Cetinkaya B, Cicek M, Sémeril D, Bruneau C, Dixneuf PH (2004) Eur J Inorg Chem, p 418 Google Scholar
  69. 69.
    Milton MD, Onodera G, Nishibayashi Y, Uemura S (2004) Org Lett 6:3993 CrossRefGoogle Scholar
  70. 70.
    Dieltiens N, Stevens CV, De Vos D, Allaert B, Drozdzak R, Verpoort F (2004) Tetrahedron Lett 45:8995 CrossRefGoogle Scholar
  71. 71.
    Michalak M, Wicha J (2005) Synlett, p 2277 Google Scholar
  72. 72.
    Dias EL, Grubbs RH (1998) Organometallics 17:2758 CrossRefGoogle Scholar
  73. 73.
    Hinze AG (1973) Recl Trav Chim Pays-Bas 92:542 Google Scholar
  74. 74.
    Iwata R, Ogata I (1973) Tetrahedron 29:2753 CrossRefGoogle Scholar
  75. 75.
    Ogata I, Iwata R, Ikeda Y (1970) Tetrahedron Lett 34:3011 CrossRefGoogle Scholar
  76. 76.
    Drouin SD, Zamanian F, Fogg DE (2001) Organometallics 20:5496 CrossRefGoogle Scholar
  77. 77.
    Drouin SD, Yap GPA, Fogg DE (2000) Inorg Chem 39:5412 CrossRefGoogle Scholar
  78. 78.
    Fogg DE, Amoroso D, Drouin SD, Snelgrove J, Conrad, Zamanian F (2002) J Mol Catal A 190:177 CrossRefGoogle Scholar
  79. 79.
    Watson MD, Wagener KB (2000) Macromolecules 33:3196 CrossRefGoogle Scholar
  80. 80.
    Simal F, Demonceau A, Noels AF (1999) Tetrahedon Lett 40:5689 CrossRefGoogle Scholar
  81. 81.
    Simal F, Demonceau A, Noels AF (1999) Angew Chem Int Ed 38:538 CrossRefGoogle Scholar
  82. 82.
    Bielawski CW, Louie J, Grubbs RH (2000) J Am Chem Soc 122:12872 CrossRefGoogle Scholar
  83. 83.
    Louie J, Bielawski CW, Grubbs RH (2001) J Am Chem Soc 123:11312 CrossRefGoogle Scholar
  84. 84.
    Fürstner A, Leitner A (2003) Angew Chem Int Ed 42:308 CrossRefGoogle Scholar
  85. 85.
    Borsting P, Nielsen P (2002) Chem Commun, p 2140 Google Scholar
  86. 86.
    Schmidt B, Pohler M (2003) Org Biomol Chem 1:2512 CrossRefGoogle Scholar
  87. 87.
    Van Otterlo WAL, Coyanis EM, Panayides JL, de Konig CB, Fernandes MA (2005) Synlett, p 501 Google Scholar
  88. 88.
    Kim BG, Snapper ML (2005) J Am Chem Soc 127:ASAP Google Scholar
  89. 89.
    Monnier F, Castillo D, Dérien S, Toupet L, Dixneuf PH (2003) Angew Chem Int Ed 42:5474 CrossRefGoogle Scholar
  90. 90.
    Eckert M, Monnier F, Shchetnikov GT, Titanyuk ID, Osipov SN, Toupet L, Dérien S, Dixneuf PH (2005) Org Lett 7:3741 CrossRefGoogle Scholar
  91. 91.
    Watanabe M, Murata K, Ikariya T (2003) J Am Chem Soc 125:7508 CrossRefGoogle Scholar
  92. 92.
    Watanabe M, Ikagawa A, Wang H, Murata K, Ikariya T (2004) J Am Chem Soc 126:11148 CrossRefGoogle Scholar
  93. 93.
    Guo R, Morris RH, Song D (2005) J Am Chem Soc 127:516 CrossRefGoogle Scholar
  94. 94.
    Huang WS, Hu QS, Pu L (1999) J Org Chem 64:7940 CrossRefGoogle Scholar
  95. 95.
    Doucet H, Ohkuma T, Murata K, Yokozawa T, Kozawa M, Katayama E, England AF, Ikariya T, Noyori R (1998) Angew Chem Int Ed Engl 37:1703 CrossRefGoogle Scholar
  96. 96.
    Yu HB, Hu QS, Pu L (2000) J Am Chem Soc 122:6500 CrossRefGoogle Scholar
  97. 97.
    Grigg R, Sridharan V, York M (1998) Tetrahedron Lett 39:4139 CrossRefGoogle Scholar
  98. 98.
    Grigg R, York M (2000) Tetrahedron Lett 41:7255 CrossRefGoogle Scholar
  99. 99.
    Cossy J, Bargiggia FC, Bouzbouz S (2002) Tetrahedron Lett 43:6715 CrossRefGoogle Scholar
  100. 100.
    Cossy J, Bargiggia FC, Bouzbouz S (2003) Org Lett 5:459 CrossRefGoogle Scholar
  101. 101.
    Nishibayashi Y, Milton MD, Inada Y, Yoshikawa M, Wakiji I, Hidai M, Uemura S (2005) Chem Eur J 11:1433 CrossRefGoogle Scholar
  102. 102.
    Nishibayashi Y, Yoshikawa M, Inada Y, Milton MD, Hidai M, Uemura S (2003) Angew Chem Int Ed 42:2681 CrossRefGoogle Scholar
  103. 103.
    Anorbe L, Dominguez G, Prez-Castells J (2004) Chem Eur J 10:4938 CrossRefGoogle Scholar
  104. 104.
    Bruneau C (2005) Angew Chem Int Ed 44:2328 CrossRefGoogle Scholar
  105. 105.
    Nishibayashi Y, Yoshikawa M, Inada Y, Hidai M, Uemura S (2004) J Am Chem Soc 126:16066 CrossRefGoogle Scholar
  106. 106.
    Milton MD, Inada Y, Nishibayashi Y, Uemura S (2004) Chem Commun, p 2712 Google Scholar
  107. 107.
    Larsson ALE, Persson BA, Bäckvall JE (1997) Angew Chem Int Ed Engl 36:1211 CrossRefGoogle Scholar
  108. 108.
    Martin-Matute B, Edin M, Bogar K, Kaynak B, Bäckvall JE (2005) J Am Chem Soc 127:8817 CrossRefGoogle Scholar
  109. 109.
    Choi JH, Kim YH, Nam SH, Shin ST, Kim MJ, Park J (2002) Angew Chem Int Ed 41:2373 CrossRefGoogle Scholar

Authors and Affiliations

  • Christian Bruneau
    • 1
    Email author
  • Sylvie Dérien
    • 1
  • Pierre H. Dixneuf
    • 1
  1. 1.Institut de Chimie de RennesUMR6509, Université de Rennes-CNRS, Organométalliques et CatalyseRennes CedexFrance

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