Selective transformations of alkynes with ruthenium catalysts

(Note: The full text of this document is currently only available in the PDF Version )

Christian Bruneau and Pierre H. Dixneuf


Abstract

The electrophilic activation of terminal alkynes by suitable ruthenium(II) catalyst precursors has provided selective access to enol esters, functional dienes, ketoesters and furans. The step-by-step modification of the ligands of simple complexes such as (arene)RuCl2(PR3), [Ru(µ-O2CH)(CO)2(PR3)]2 or (diphosphine)Ru(allyl)2, has allowed the determination of efficient catalytic conditions for regio- and stereo-selective additions to alkynes. The utilization of electron-rich ruthenium(II) complexes containing the bulky pentamethylcyclopentadienyl ligand, has made possible the catalytic carbon–carbon bond forming reaction from alkynes and allyl alcohol to give unsaturated aldehydes.


References

  1. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1993 Search PubMed; S. Akutagawa, Appl. Catal. A: General, 1995, 128, 171 Search PubMed.
  2. S. H. Murahashi, T. Nota, N. Miyaguchi and T. Nakato, Tetrahedron Lett., 1992, 33, 6991 CrossRef CAS; S. H. Murahashi and T. Nota, Synthesis, 1993, 433 CrossRef CAS.
  3. T. Kondo, A. Tanaka, S. Kotachi and Y. Watanabe, J. Chem. Soc., Chem. Commun., 1995, 413 RSC; S. W. Zhang, T. Mitsudo, T. Kondo and Y. Watanabe, J. Organomet. Chem., 1995, 485, 55 CrossRef CAS; T. Mitsudo, S. W. Zhang, M. Nagao and Y. Watanabe, J. Chem. Soc., Chem. Commun., 1991, 598 RSC; T. Mitsudo, Y. Hori, Y. Yamakawa and Y. Watanabe, J. Org. Chem., 1987, 52, 2230 CrossRef CAS.
  4. N. Chatani, Y. Fukumoto, T. Ida and S. Murai, J. Am. Chem. Soc., 1993, 115, 11 614 CrossRef CAS; S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda and N. Chatani, Nature (London), 1993, 366, 529 CrossRef CAS; S. Murai, J. Synth. Org. Chem. Jpn., 1994, 52, 120 Search PubMed; F. Kakiuchi, Y. Tanaka, T. Sato, N. Chatani and S. Murai, Chem. Lett., 1995, 679 CAS; F. Kakiuchi, Y. Yamamoto, N. Chatani and S. Murai, Chem. Lett., 1995, 681 CAS.
  5. H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki and K. Itoh, Bull. Chem. Soc. Jpn., 1995, 68, 1247 CAS; A. Demonceau, E. Abreu Dias, C. A. Lemoine, A. W. Stumpf and A. F. Noels, Tetrahedron Lett., 1995, 36, 3519 CrossRef CAS; S. H. Kim, W. J. Zuercher, N. B. Bowden and R. H. Grubbs, J. Org. Chem., 1996, 61, 1073 CrossRef CAS.
  6. D. M. Lynn, S. Kanaoka and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 784 CrossRef CAS; R. H. Grubbs, S. J. Miller and G. C. Fu, Acc. Chem. Res., 1995, 28, 446 CrossRef CAS; A. W. Stumpf, E. Saive, A. Demonceau and A. F. Noels, J. Chem. Soc., Chem. Commun., 1995, 1127 RSC.
  7. B. M. Trost, Angew. Chem., Int. Ed. Engl., 1995, 34, 259 CrossRef CAS.
  8. H. Le Bozec, K. Ouzzine and P. H. Dixneuf, Organometallics, 1991, 10, 2768 CrossRef CAS; H. Le Bozec, D. Pilette and P. H. Dixneuf, New J. Chem., 1990, 14, 793 Search PubMed; H. Le Bozec, K. Ouzzine and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1989, 219 RSC; D. Pilette, S. Moreau, H. Le Bozec, P. H. Dixneuf, J. Corrigan and A. J. Carty, J. Chem. Soc., Chem. Commun., 1994, 409 RSC; P. Haquette, N. Pirio, D. Touchard, L. Toupet and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1993, 163 RSC; D. Touchard, P. Haquette, A. Daridor, L. Toupet and P. H. Dixneuf, J. Am. Chem. Soc., 1994, 116, 11157 CrossRef CAS; D. Touchard, N. Pirio and P. H. Dixneuf, Organometallics, 1995, 14, 4920 CrossRef CAS.
  9. J. P. Monthéard, M. Camps, G. Seytre, J. Guillet and J. C. Dubois, Makromol. Chem., 1978, 72, 45 CAS; A. Seidel, E. Jägers and F. Bylsma, Eur. Pat., 0574725 A1, 1993 Search PubMed.
  10. E. S. Rothman, S. S. Hecht, P. E. Pfeffer and L. S. Silbert, J. Org. Chem., 1972, 37, 3551 CrossRef CAS; P. F. Hudrlik and A. M. Hudrlik, J. Org. Chem., 1973, 38, 4254 CrossRef CAS; R. C. Larock, K. Oertle and K. M. Beatty, J. Am. Chem. Soc., 1980, 102, 1966 CrossRef CAS; Y. Kita, S. Akai, N. Ajimura, M. Yoshigi, T. Tsugoshi, H. Yasuda and Y. Tamura, J. Org. Chem., 1986, 51, 4150 CrossRef CAS.
  11. C. Ruppin and P. H. Dixneuf, Tetrahedron Lett., 1986, 27, 6323 CrossRef CAS.
  12. C. Bruneau, M. Neveux, Z. Kabouche and P. H. Dixneuf, Synlett, 1991, 755 CrossRef.
  13. K. Philippot, D. Devanne and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1990, 1199 RSC.
  14. C. Ruppin, P. H. Dixneuf and S. Lécolier, Tetrahedron Lett., 1988, 29, 5365 CrossRef CAS.
  15. E. S. Rothman and G. G. Moore, Tetrahedron Lett., 1969, 2553 CrossRef CAS; E. S. Rothman, G. G. Moore and A. N. Speca, Tetrahedron Lett., 1969, 5205 CrossRef CAS.
  16. J. Tsuji, I. Minami and I. Shimizu, Tetrahedron Lett., 1983, 24, 5205 CrossRef.
  17. M. Kosugi, I. Hagiwara, T. Sumiya and T. Migita, J. Chem. Soc., Chem. Commun., 1983, 344 RSC.
  18. Y. Masuyama, T. Sakai and Y. Kurusu, Tetrahedron Lett., 1993, 34, 653 CrossRef CAS; Y. Masuyama, T. Sakai, T. Kato and Y. Kurusu, Bull. Chem. Soc. Jpn., 1994, 67, 2265 CAS.
  19. A. Demonceau, E. Saive, Y. de Froidmont, A. F. Noels and A. J. Hubert, Tetrahedron Lett., 1992, 33, 2009 CrossRef CAS; W. B. Motherwell and L. R. Roberts, J. Chem. Soc., Chem. Commun., 1992, 1582 RSC.
  20. M. E. Jung and J. P. Hudspeth, J. Am. Chem. Soc., 1978, 100, 4309 CrossRef CAS; L. F. Tietze, A. Montenbruck and C. Schneider, Synlett, 1994, 509 CrossRef CAS.
  21. N. Sakai, K. Nozaki, K. Mashima and H. Takaya, J. Am. Chem. Soc., 1993, 115, 7033 CrossRef CAS.
  22. J. E. W. van Melick, J. W. Scheeren and R. J. F. Nivard, Tetrahedron Lett., 1971, 2083 CrossRef CAS; Y. Kita, H. Maeda, K. Onari, T. Okuno and T. Tamura, J. Chem. Soc., Perkin Trans. 1, 1993, 2999 RSC; Y. Kita, S. Akai, M. Yoshigi, Y. Nakajima, H. Yasuda and Y. Tamura, Tetrahedron Lett., 1984, 25, 6067; D. Villemin, B. Labiad and A. Loupy, Synth. Commun., 1993, 23, 419 CAS.
  23. C. Larpent and X. Chasseray, New J. Chem., 1993, 17, 851 Search PubMed; M. Uemura, H. Nishimura, S. Yamada, K. Nakamura and Y. Hayashi, Tetrahedron Lett., 1993, 34, 6581 CrossRef CAS; Y. Kume and H. Ohta, Tetrahedron Lett., 1992, 33, 6367 CrossRef CAS; M. Lobell and M. P. Schneider, Tetrahedron: Asymmetry, 1993, 4, 1027 CrossRef CAS.
  24. M. Neveux, C. Bruneau and P. H. Dixneuf, J. Chem. Soc., Perkin Trans. 1, 1991, 1197 RSC.
  25. Z. Kabouche, C. Bruneau and P. H. Dixneuf, Tetrahedron Lett., 1991, 32, 5359 CrossRef CAS.
  26. B. Seiller, D. Heins, C. Bruneau and P. H. Dixneuf, Tetrahedron, 1995, 51, 10 901 CrossRef CAS.
  27. B. Seiller, C. Bruneau and P. H. Dixneuf, Synlett, 1995, 707 CrossRef CAS.
  28. M. Neveux, C. Bruneau, S. Lécolier and P. H. Dixneuf, Tetrahedron, 1993, 49, 2629 CrossRef CAS.
  29. M. Neveux, B. Seiller, F. Hagedorn, C. Bruneau and P. H. Dixneuf, J. Organomet. Chem., 1993, 451, 133 CrossRef CAS.
  30. O. Lavastre and P. H. Dixneuf, J. Organomet. Chem., 1995, 488, C9 CrossRef CAS.
  31. O. Lavastre, P. Bebin, O. Marchaland and P. H. Dixneuf, J. Mol. Catal. A, 1996, 108, 29 CrossRef CAS.
  32. C. Bruneau, Z. Kabouche, M. Neveux, B. Seiller and P. H. Dixneuf, Inorg. Chim. Acta, 1994, 222, 155 CrossRef CAS.
  33. D. Devanne, C. Ruppin and P. H. Dixneuf, J. Org. Chem., 1988, 53, 925 CrossRef CAS.
  34. C. Darcel, C. Bruneau, P. H. Dixneuf and G. Neef, J. Chem. Soc., Chem. Commun., 1994, 333 RSC.
  35. B. Seiller, C. Bruneau and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1994, 493 RSC.
  36. B. Seiller, C. Bruneau and P. H. Dixneuf, Tetrahedron, 1995, 51, 13089 CrossRef CAS.
  37. R. Mahé, Y. Sasaki, C. Bruneau and P. H. Dixneuf, J. Org. Chem., 1989, 54, 1518 CrossRef CAS.
  38. M. Cooke, R. J. Goodfellow, M. Green and G. Parker, J. Chem. Soc. A, 1971, 16 RSC; J. P. Genêt, S. Mallart, C. Pinel, S. Jugé and J. A. Laffitte, Tetrahedron: Asymmetry, 1991, 2, 43 CrossRef CAS.
  39. H. Doucet, J. Höfer, C. Bruneau and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1993, 850 RSC.
  40. H. Doucet, B. Martin-Vaca, C. Bruneau and P. H. Dixneuf, J. Org. Chem., 1995, 60, 7247 CrossRef CAS.
  41. B. M. Trost, G. Dyker and R. J. Kulawiec, J. Am. Chem. Soc., 1990, 112, 7809 CrossRef CAS.
  42. S. Dérien and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1994, 2551 RSC.
  43. S. Dérien, D. Jan and P. H. Dixneuf, Tetrahedron, 1996, 52, 5511 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.