New Ruthenium Catalysts for Alkene Metathesis

  • Cédric Fischmeister
  • Pierre H. Dixneuf
Conference paper
Part of the NATO Science Series book series (NAII, volume 243)

The main developments in ruthenium catalyst design for alkene metathesis covering the last 4 years is presented. These new catalysts are essentially based on modifications brought to Grubbs- or Hoveyda-type catalysts and the generation of catalysts by activation of propargyl derivatives leading to ruthenium–allenylidene, – indenylidene, and alkenylcarbene catalysts.

Keywords

Alkene Alkyne Diene Allyl Phosphonium 

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References

  1. [1]
    Hérisson, J.L., Chauvin, Y. (1971) Makromol. Chem. 141:161.CrossRefGoogle Scholar
  2. [2](a)
    Schrock, R.R., Murdzek, J.S., Bazan, G.C., Robbins, J., DiMare, M., O’Regan, M. (1990) J. Am. Chem. Soc. 112:3875;CrossRefGoogle Scholar
  3. (b).
    Schrock, R.R. (2004) J. Mol. Catal A: Chem. 213:21.CrossRefGoogle Scholar
  4. [3]
    Nguyen, S.T., Johnson, L.K., Grubbs, R.H., Ziller, J.W. (1992) J. Am. Chem. Soc. 114:3974.CrossRefGoogle Scholar
  5. [4]
    Schwab, P., France, M.B., Ziller, J.W., Grubbs, R.H. (1995) Angew. Chem. Int. Edit. 34:2039.CrossRefGoogle Scholar
  6. [5](a)
    Harrity, J.P.A., La, D.S., Cefalo, D.R., Visser, M.S., Hoveyda, A.H. (1998) J. Am. Chem. Soc. 120:2343;CrossRefGoogle Scholar
  7. (b).
    Kingsbury, J.S., Harrity, J.P.A., Bonitatebus, P.J., Hoveyda, A.H. (1999) J. Am. Chem. Soc. 121:791.CrossRefGoogle Scholar
  8. [6](a)
    Huang, J., Nolan, S.P., Petersen, J.L. (1999) J. Am. Chem. Soc. 121:2674;CrossRefGoogle Scholar
  9. (b).
    Scholl, M., Trnka, T.M., Morgan, J.P., Grubbs, R.H. (1999) Tetrahedron Lett.40:2247;CrossRefGoogle Scholar
  10. (c).
    Weskamp, T., Kohl, F.J., Hieringer, W., Gleich, D., Herrmann, W.A. (1999) Angew. Chem. Int. Edit. 38:2416.CrossRefGoogle Scholar
  11. [7]
    Scholl, M., Ding, S., Lee, C.W., Grubbs, R.H. (1999) Org. Lett. 1:953.CrossRefGoogle Scholar
  12. [8](a)
    Garber, S.B., Kingsbury, J.S., Gray, B.L., Hoveyda, A.H. (2000) J. Am. Chem. Soc.122:8168;CrossRefGoogle Scholar
  13. (b).
    Gessler, S., Randl, S., Blechert, S.,(2000) Tetrahedron Lett. 41:9973.CrossRefGoogle Scholar
  14. [9](a)
    Sanford, M.S., Love, J.A., Grubbs, R.H. (2001) Organometallics 20:5314;CrossRefGoogle Scholar
  15. (b).
    Love, J.A., Morgan, J.P., Trnka, T.M., Grubbs, R.H. (2002) Angew. Chem. Int. Edit. 41:4035-4037;CrossRefGoogle Scholar
  16. (c).
    Trnka, T.M., Morgan, J.P., Sanford, M.S., Wilhelm, T.E., Scholl, M., Choi, T-L., Ding, S., Day, M.W., Grubbs, R.H. (2003) J. Am. Chem. Soc. 125:2546.CrossRefGoogle Scholar
  17. [10](a)
    Fürstner, A., Picquet, M., Bruneau, C., Dixneuf, P.H. (1998) Chem. Commun. 1315;Google Scholar
  18. (b).
    Picquet, M., Bruneau, C., Dixneuf, P.H. (1998) Chem. Commun. 2249;Google Scholar
  19. (c).
    Fürstner, A., Liebl, M., Lehmann, C.W., Piquet, M., Kunz, R., Bruneau, C., Touchard, D., Dixneuf, P.H. (2000) Chem. Eur. J. 6:1847;CrossRefGoogle Scholar
  20. (d).
    Osipov, S.N., Kobelikova, N.M., Schetnikov, G.T., Kolomiets, A.F., Bruneau, C., Dixneuf, P.H. (2001) Synlett 5:621;Google Scholar
  21. (e).
    Osipov, S.N., Artyushin, O.I., Kolomiets, A.F., Bruneau, C., Dixneuf, P.H. (2000) Synlett 7:1031;Google Scholar
  22. (f).
    Castarlenas, R., Fischmeister, C., Bruneau, C., Dixneuf, P.H. (2004) J. Mol. Catal A: Chem. 213:31;CrossRefGoogle Scholar
  23. (g).
    Picquet, M., Touchard, D., Bruneau, C., Dixneuf, P.H. (1999) New J. Chem. 141.Google Scholar
  24. [11](a)
    Castarlenas, R., Dixneuf, P. (2003) Angew. Chem. Int. Edit. 42:4524;CrossRefGoogle Scholar
  25. (b).
    Castarlenas, R., Vovard, C., Fischmeister, C., Dixneuf, P. (2006) J. Am. Chem. Soc. 128:4079.CrossRefGoogle Scholar
  26. [12]
    Weskamp, T., Schattenmann, W.C., Spiegler, M., Herrmann, W.A. (1998) Angew. Chem. Int. Edit. 37:2490.CrossRefGoogle Scholar
  27. [13]
    Kingsbury, J.S., Hoveyda, A.H. (2005) J. Am. Chem. Soc. 127:4510.CrossRefGoogle Scholar
  28. [14]
    Trnka, T., Grubbs, R.H. (2001) Acc. Chem. Res. 34:18.CrossRefGoogle Scholar
  29. [15]
    Forman, G.S., McConnell, A.E., Hanton, M.J., Slawin, A.M.Z., Tooze, R.P., Janse van Rensburg, W., Meyer, W.H., Dwyer, C., Kirk, M.M., Serfontein, D.W. (2004) Organometallics 23:4834.CrossRefGoogle Scholar
  30. [16](a)
    Anderson, D.R., Hickstein, D.D., O’Leary, D.J., Grubbs, R.H. (2006) J. Am. Chem. Soc. 128:8386 and references therein;CrossRefGoogle Scholar
  31. (b).
    Cavallo, L. (2002) J. Am. Chem. Soc. 124:8965.CrossRefGoogle Scholar
  32. [17](a)
    Morgan, J.P., Grubbs, R.H. (2000) Org. Lett. 2:3153;CrossRefGoogle Scholar
  33. (b).
    Lynn, D.M., Mohr, B., Grubbs, R.H., Henling, L.M., Day, M.W. (2000) J. Am. Chem. Soc. 122:6601;CrossRefGoogle Scholar
  34. (c).
    Huang, J., Schanz, H.J., Stevens, E.D., Nolan, S.P. (1999) Organometallics 18:5375;CrossRefGoogle Scholar
  35. (d).
    Rivard, M., Blechert, S. (2003) Eur. J. Org. Chem. 2225.Google Scholar
  36. [18]
    Love, J.A., Sanford, M.S., Day, M.W., Grubbs, R.H. (2003) J. Am. Chem. Soc. 125:10103.CrossRefGoogle Scholar
  37. [19]
    Corrêa da Costa, R., Gladysz, J.A. (2006) Chem. Commun. 2619.Google Scholar
  38. [20]
    Fürstner, A., Ackermann, L., Gabor, B., Goddard, R., Lehmann, C.W., Mynott, R., Stelzer, F., Thiel, O.R. (2001) Chem. Eur. J. 7:3236.CrossRefGoogle Scholar
  39. [21]
    Yun, J., Marinez, E.R., Grubbs, R.H. (2004) Organometallics 23:4172.CrossRefGoogle Scholar
  40. [22]
    Prühs, S., Lehmann, C.W., Fürstner, A. (2004) Organometallics 23:280.CrossRefGoogle Scholar
  41. [23]
    Ritter, T., Day, M.W., Grubbs, R.H. (2006) J. Am. Chem. Soc. 128:11768.CrossRefGoogle Scholar
  42. [24]
    Romero, P.E., Piers, W.E., McDonald, R. (2004) Angew. Chem. Int. Edit. 43:6161.CrossRefGoogle Scholar
  43. [25]
    Sanford, M.S., Henling, L.M., Day, M.W., Grubbs, R.H. (2000) Angew. Chem. Int. Edit. 39:3451.CrossRefGoogle Scholar
  44. [26]
    Buchowicz, W., Ingold, F., Mol, J.C., Lutz, M., Spek, A.L. (2001) Chem. Eur. J. 7:2842.CrossRefGoogle Scholar
  45. [27]
    Conrad, J.C., Amoroso, D., Czechura, P., Yap, G.P.A., Fogg, D.E. (2003) Organometallics 22:3634.CrossRefGoogle Scholar
  46. [28]
    Monfette, S., Fogg, D.E. (2006) Organometallics 25:1940.CrossRefGoogle Scholar
  47. [29]
    Conrad, J.C., Parnas, H.H., Snelgrove, J.L., Fogg, D.E. (2005) J. Am. Chem. Soc. 127:11882.CrossRefGoogle Scholar
  48. [30]
    Halbach, T.S., Mix, S., Fischer, D., Maechling, S., Krause, J.O., Sievers, C., Blechert, S., Nuyken, O., Buchmeiser, M.R. (2005) J. Org. Chem. 70:4687.CrossRefGoogle Scholar
  49. [31]
    Wakamatsu, H., Blechert, S. (2002) Angew. Chem. Int. Edit. 41:2403.CrossRefGoogle Scholar
  50. [32]
    Grela, K., Harutyunyan, S., Michrowska, A. (2002) Angew. Chem. Int. Edit. 41:4038.CrossRefGoogle Scholar
  51. [33]
    Michrowska, A., Bujok, R., Harutyunyan, S., Sashuk, V., Dolgonos, G., Grela, K. (2004) J. Am. Chem. Soc. 126:9318.CrossRefGoogle Scholar
  52. [34]
    Michrowska, A., Gulaski, L., Kaczmarska, Z., Mennecke, K., Kirschning, A., Grela, K. (2006) Green Chem. 8:685.CrossRefGoogle Scholar
  53. [35]
    Despagnet-Ayoub, E., Grubbs, R.H. (2005) Organometallics 24:338.CrossRefGoogle Scholar
  54. [36]
    Vehlow, K., Maechling, S., Blechert, S. (2006) Organometallics 25:25.CrossRefGoogle Scholar
  55. [37]
    Fürstner, A., Davies, P.W., Lehmann, C.W. (2005) Organometallics 24:4065.CrossRefGoogle Scholar
  56. [38]
    Krause, J.O., Nuyken, O., Wurst, K., Buchmeiser, MR. (2004) Chem. Eur. J. 10:777.CrossRefGoogle Scholar
  57. [39](a)
    Ung, T., Hejl, A., Grubbs, R.H., Schrodi, Y. (2004) Organometallics 23:5399;CrossRefGoogle Scholar
  58. (b).
    Barbasiewicz, M., Szadkowska, A., Bujok, R., Grela, K. (2006) Organometallics 25:3599;CrossRefGoogle Scholar
  59. (c).
    Slugovc, C., Burtscher, C., Stelzer, F., Mereiter, K. (2005) Organometallics 24:2255.CrossRefGoogle Scholar
  60. [40](a)
    Fürstner, A., Thiel, O.R., Lehmann, C.W.(2002) Organometallics 25:3599;Google Scholar
  61. (b).
    Slugovc, C., Perner, B., Stelzer, F., Mereiter, K.(2004) Organometallics 23:3622.CrossRefGoogle Scholar
  62. [41](a)
    Opstal, T., Verpoort, F. (2003) Angew. Chem. Int. Edit. 42:2876;CrossRefGoogle Scholar
  63. (b).
    Drozdak, R., Allaert, B., Ledoux, N., Dragutan, I., Dragutan, V., Verpoort, F. (2005) Adv. Synth. Catal. 347:1721.CrossRefGoogle Scholar
  64. [42](a)
    Dragutan, V., Dragutan, I., Verpoort, F. (2005) Platinum Metals Rev. 49:33;CrossRefGoogle Scholar
  65. (b).
    Dragutan, I., Dragutan, V., (2006) Platinum Metals Rev. 50:181;Google Scholar
  66. (c).
    Rigaut, S., Touchard, D., Dixneuf, P.H. (2004) Coord. Chem. Rev. 248:1585.Google Scholar
  67. [43]
    Sémeril, D., Le Nôtre, J., Bruneau, C., Dixneuf, P.H., Kolomiets, A.F., Osipov, S.N. (2001) New J. Chem. 25:16.CrossRefGoogle Scholar
  68. [44]
    Castarlenas, R., Sémeril, D., Noels, A.F., Demonceau, A., Dixneuf, P.H. (2002) J. Organomet. Chem. 663:235.CrossRefGoogle Scholar
  69. [45]
    Basseti, M., Centola, F., Sémeril, D., Bruneau, C., Dixneuf, P.H.(2003) Organometallics 22:4459.CrossRefGoogle Scholar
  70. [46]
    Sémeril, D., Olivier-Bourbigou, H., Bruneau, C., Dixneuf, P.H. (2002) Chem. Commun. 146.Google Scholar
  71. [47]
    Csihony, Sz., Fischmeister, C., Bruneau, C., Horváth, I.T., Dixneuf, P.H. (2002) New J. Chem. 26:1667.CrossRefGoogle Scholar
  72. [48]
    Saoud, M., Romerosa, A., Peruzzini, M. (2000) Organometallics 20:4005.CrossRefGoogle Scholar
  73. [49]
    Jafarpour, L., Schanz, H-J., Stevens, E.D., Nolan, S.P. (1999) Organometallics 18:5416.CrossRefGoogle Scholar
  74. [50](a)
    Fürstner, A., Hill, A.F., Liebl, M., Wilton-Ely, J.D.E.T. (1999) Chem. Commun. 601;Google Scholar
  75. (b).
    Fürstner, A., Grabowski, J., Lehman, C.N. (1999) J. Org. Chem. 64:827 and references therein.Google Scholar
  76. [51]
    Fürstner, A., Guth, O., Duffets, A., Seidel, G., Liebl, M., Gabor, B., Mynott, R. (2001) Chem. Eur. J. 7:4811.CrossRefGoogle Scholar
  77. [52]
    Castarlenas, R., Eckert, M., Dixneuf, PH. (2005) Angew. Chem. Int. Edit. 44:2576.CrossRefGoogle Scholar

Copyright information

© Springer 2007

Authors and Affiliations

  • Cédric Fischmeister
    • 1
  • Pierre H. Dixneuf
    • 1
  1. 1.Catalyse et Organométalliques CNRSUniversité de Rennes 1Institut Sciences Chimiques de Rennes BAT 10CRennesFrance

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