An ionic liquid-tagged second generation Hoveyda-Grubbs ruthenium carbene complex as highly reactive and recyclable catalyst for ring-closing metathesis of di-, tri- and tetrasubstituted dienes

Journal of Organometallic Chemistry

Volumn 690, Issue 15, 2005, Pages 3577-3584

  Yao, Qingwei ^a   Sheets, Matthew ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Carbene complexes; Grubbs catalysts; Ionic liquids; Olefin metathesis; Ruthenium

Indexed keywords

CATALYSIS; CATALYSTS; IONIC CONDUCTION; MOLECULAR STRUCTURE; OLEFINS; RUTHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

CARBENE COMPLEXES; GRUBBS CATALYSTS; IONIC LIQUIDS; OLEFIN METATHESIS;

COMPLEXATION;

EID: 22944432492     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.03.031     Document Type: Article

References (67)

1. P. Schwab, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 118 1996 100
2. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
3. M. Scholl, T.M. Trnka, J.P. Morgan, and R.H. Grubbs Tetrahedron Lett. 40 1999 2247
4. J. Huang, E.D. Stevens, S.P. Nolan, and J.F. Petersen J. Am. Chem. Soc. 121 1999 2674
5. Selected reviews: M. Schuster, and S. Blechert Angew. Chem., Int. Ed. Engl. 36 1997 2036
6. S.K. Armstrong J. Chem. Soc., Perkin Trans. 1 1998 371
7. R.H. Grubbs, and S. Chang Tetrahedron 54 1998 4413
8. A. Fürstner Angew. Chem., Int. Ed. 39 2000 3012
9. T.M. Trnka, and R.H. Grubbs Accounts Chem. Res. 34 2001 18
10. S. Blechert Angew. Chem., Int. Ed. 42 2003 1900
11. J.S. Kingsbury, J.P.A. Harrity, P.J. Bonitatebus, and A.H. Hoveyda J. Am. Chem. Soc. 121 1999 791
12. S.B. Garber, J.S. Kingsbury, B.L. Gray, and A.H. Hoveyda J. Am. Chem. Soc. 122 2000 8168
13. Also see: S. Gessler, S. Randl, and S. Blechert Tetrahedron Lett. 41 2000 9973
14. For a short account on the development and application of these catalysts, see: A.H. Hoveyda, D.G. Gillingham, J.J. Van Veldhuizen, O. Kataoka, S.B. Garber, J.S. Kingsbury, and J.P.A. Harrity Org. Biomol. Chem. 2 2004 1
15. For related catalysts, see: H. Wakamatsu, and S. Blechert Angew. Chem., Int. Ed. 41 2002 794
16. H. Wakamatsu, and S. Blechert Angew. Chem., Int. Ed. 41 2002 2403
17. M. Zaja, S.J. Connon, A.M. Dunne, M. Rivard, N. Buschmann, J. Jiricek, and S. Blechert Tetrahedron 59 2003 6545
18. K. Grela, S. Harutyunyan, and A. Michrowska Angew. Chem., Int. Ed. 41 2002 4038
19. A. Michrowska, R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, and K. Grela J. Am. Chem. Soc. 126 2004 9318
20. S.T. Nguyen, and R.H. Grubbs J. Organomet. Chem. 497 1995 195
21. M. Ahmed, A.G.M. Barrett, D.C. Braddock, S.M. Cramp, and P.A. Procopiou Tetrahedron Lett. 40 1999 8657
22. M. Ahmed, T. Arnauld, A.G.M. Barrett, D.C. Braddock, and P.A. Procopiou Synlett 2000 1007
23. S.C. Schürer, S. Gessler, N. Buschmann, and S. Blechert Angew. Chem., Int. Ed. 39 2000 3898
24. L. Jafarpour, and S.P. Nolan Org. Lett. 2 2000 4075
25. J. Dowden, and J. Savovic Chem. Commun. 2001 37
26. M. Mayr, B. Mayr, and M.R. Buchmeiser Angew. Chem., Int. Ed. 40 2001 3839
27. J.S. Kingsbury, S.B. Garber, J.M. Giftos, B.L. Gray, M.M. Okamoto, R.A. Farrer, J.T. Fourkas, and A.H. Hoveyda Angew. Chem., Int. Ed. 40 2001 4251
28. S. Randl, N. Buschmann, S.J. Connon, and S. Blechert Synlett 10 2001 1547
29. L. Jafarpour, M.P. Heck, C. Baylon, H.L. Lee, C. Mioskowski, and S.P. Nolan Organometallics 21 2002 671
30. S.J. Connon, A.M. Dune, and S. Blechert Angew. Chem., Int. Ed. 41 2002 3835
31. K. Grela, M. Tryznowski, and M. Bieniek Tetrahedron Lett. 43 2002 9055
32. S. Gibson, and V.M. Swamy Adv. Synth. Catal. 344 2002 619
33. M. Mayr, M.R. Buchmeiser, and K. Wurst Adv. Synth. Catal. 344 2002 712
34. S. Varray, R. Lazaro, J. Martinez, and F. Lamaty Organometallics 22 2003 2426
35. N. Audic, H. Clavier, M. Mauduit, and J.-C. Guillemin J. Am. Chem. Soc. 125 2003 9248
36. H. Clavier, N. Audic, M. Mauduit, and J.-C. Guillemin Chem Commun. 2004 2282
37. Q. Yao Angew. Chem., Int. Ed. 39 2000 3896
38. Q. Yao, and A.R. Motta Tetrahedron Lett. 45 2004 2447
39. Q. Yao, and Y. Zhang J. Am. Chem. Soc. 126 2004 74
40. I.T. Horváth, and J. Rabái Science 266 1994 72
41. For selected leading reviews on fluorous biphasic chemistry and fluorous separation, see: I.T. Horváth Accounts Chem. Res. 31 1998 641
42. D.P. Curran Angew. Chem., Int. Ed. Engl. 37 1998 1174
43. E. de Wolf, G. van Koten, and B.-J. Deelman Chem. Soc. Rev. 28 1999 37
44. R.H. Fish Chem. Eur. J. 5 1999 1677
45. E.G. Hope, and A.M. Stuart J. Fluorine Chem. 100 1999 75
46. A.P. Dobbs, and M.R. Kimberly J. Fluorine Chem. 118 2002 3
47. J. Yoshida, and K. Itami Chem. Rev. 102 2002 3693
48. Selected recent reviews on ionic liquids and their application in transition metal-catalyzed reactions: T. Welton Chem. Rev. 99 1999 2071
49. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772
50. R. Sheldon Chem. Commun. 2001 2399
51. J. Dupont, R.F. de Souza, and P.A. Suarez Chem. Rev. 102 2002 3667
52. P. Wasserscheid, and T. Welton Ionic liquids in synthesis 2003 Wiley-VCH Weinheim, Germany
53. R.C. Buijsman, E. van Vuuren, and J.G. Sterrenburg Org. Lett. 3 2001 3785
54. D. Semeril, H. Olivier-Bourbigou, C. Bruneau, and P.H. Dixneuf Chem. Commun. 2002 146
55. K.G. Mayo, E.H. Nearhoof, and J.J. Kiddle Org. Lett. 4 2002 1567
56. S. Csihony, C. Fischmeister, C. Bruneau, I.T. Horvath, and P.H. Dixneuf New J. Chem. 26 2002 1667
57. Q. Yao, and Y. Zhang Angew. Chem., Int. Ed. 42 2003 3395
58. 6 alone as the solvent in olefin metathesis. A highly ionic reaction medium may have a detrimental effect in causing rapid catalyst decomposition. Use of large amounts of ionic liquids can limit their practical and large-scale application due to their high cost.
59. 6 and toluene was used by Mauduit and coworkers in the recycling and reuse of catalyst 12, see [4q].
60. 1H NMR spectroscopy).
61. All operations, including concentration of the reaction mixture and washing with ether, were carried out in vessels open to the air.
62. Q. Yao Org. Lett. 4 2002 42
63. J.G. Knight, and M.P. Muldowney Synlett 1995 949
64. J.A. Marco, M. Carda, S. Rodriguez, E. Castillo, and M.N. Kneeteman Tetrahedron 59 2003 4085
65. J. Polakova, M. Palecek, and M. Prochazka Coll. Czech. Chem. Commun. 4 1979 3705
66. G.C. Fu, and R.H. Grubbs J. Am. Chem. Soc. 114 1992 5426
67. Y. Tamaru, M. Hojo, and Z. Yoshida J. Org. Chem. 53 1988 5731