Silica immobilized Hoveyda type pre-catalysts: Convenient and reusable heterogeneous catalysts for batch and flow olefin metathesis

Australian Journal of Chemistry

Volumn 66, Issue 2, 2013, Pages 183-191

  Solodenko, Wladimir ^a   Doppiu, Angelino ^b   Frankfurter, René ^a   Vogt, Carla ^a   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b UMICORE AG AND CO KG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT INTERACTIONS; ENYNE METATHESIS; FLOW CONDITION; HETEROGENEOUS CATALYST; NON-POLAR; OLEFIN METATHESIS; PRECATALYSTS; RING CLOSINGS; RUTHENIUM METATHESIS; SUPPORT SURFACES; UMICORE;

CATALYSTS; OLEFINS; ORGANIC SOLVENTS; REUSABILITY; RUTHENIUM; TOLUENE;

SILICA;

EID: 84873890827     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH12434     Document Type: Article

References (53)

1. (a) Handbook of Metathesis (Ed. R. H. Grubbs) 2003 (Wiley-VCH: Weinheim).
2. (b) G. C. Vougioukalakis, R. H. Grubbs, Chem. Rev. 2010, 110, 1746. doi:10.1021/CR9002424
3. (a) W.-Y. Siau, Y. Zhang, Y. Zhao, Top. Curr. Chem. 2012, 327, 33. doi:10.1007/128-2012-315
4. (b) S. J. Meek, R. V. O'Brien, J. Llaveria, R. R. Schrock, A. H. Hoveyda, Nature 2011, 471, 461. doi:10.1038/NATURE09957
5. (c) K. Endo, R. H. Grubbs, J. Am. Chem. Soc. 2011, 133, 8525. doi:10.1021/JA202818V
6. (d) B. K. Keitz, K. Endo, M. B. Herbert, R. H. Grubbs, J. Am. Chem. Soc. 2011, 133, 9686. doi:10.1021/JA203488E
7. For a review on sustainable metathesis see: H. Clavier, K. Grela, A. Kirschning, M. Mauduit, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 6786. doi:10.1002/ANIE.200605099
8. (a) D. Barbaras, J. Brozio, I. Johannsen, T. Allmendinger, Org. Process Res. Dev. 2009, 13, 1068. doi:10.1021/OP900102A
9. (b) For oral and parenteral drug products, contaminationwith ruthenium must be less than 5 ppm and 0.5 ppm, respectively, according to the guidelines of the European Agency for the Evaluation of Medicinal Products: A. Thayer, Chem. Eng. News 2005, 83, 55.
10. C. Coperet, J.-M. Basset, Adv. Synth. Catal. 2007, 349, 78. doi:10.1002/ADSC.200600443
11. (a) L. Gulajski, M. Mauduit, K. Grela, Pure Appl. Chem. 2009, 81, 2001. doi:10.1351/PAC-CON-08-10-13
12. (b) P. Sledz, M. Mauduit, K. Grela, Chem. Soc. Rev. 2008, 37, 2433. doi:10.1039/B711482F
13. (a) A. Michrowska, K. Mennecke, U. Kunz, A. Kirschning, K. Grela, J. Am. Chem. Soc. 2006, 128, 13261. doi:10.1021/JA063561K
14. (b) E. Borré, M. Rouen, I. Laurent, M. Magrez, F. Caijo, C. Crévisy, W. Solodenko, L. Toupet, R. Frankfurter, C. Vogt, A. Kirschning, M. Mauduit, Chem.-Eur. J. 2012, in press. doi:10.1002/CHEM. 201201589
15. (a) N. Audic, H. Clavier, M. Mauduit, J. C. Guillemin, J. Am. Chem. Soc. 2003, 125, 9248. doi:10.1021/JA021484X
16. (b) H. Clavier, N. Audic, J.-C. Guillemin, M. Mauduit, Chem. Commun. 2004, 1224. doi:10.1039/B402368D
17. (c) H. Clavier, N. Audic, J.-C. Guillemin, M. Mauduit, J. Organomet. Chem. 2005, 690, 3585. doi:10.1016/J.JORGANCHEM.2005.04.009
18. (d) D. Rix, H. Clavier, Y. Coutard, L. Gulajski, K. Grela, M. Mauduit, J. Organomet. Chem. 2006, 691, 5397. doi:10.1016/J.JORGAN CHEM.2006.07.042
19. (e) D. Rix, F. Caijo, I. Laurent, L. Gulajski, K. Grela, M. Mauduit, Chem. Commun. 2007, 3771. doi:10.1039/B705451C
20. (f) E. Borre, F. Caijo, C. Crevisy, M. Mauduit, Chim. Oggi 2009, 27, 20.
21. (g) H. Clavier, S. P. Nolan, M. Mauduit, Organometallics 2008, 27, 2287. doi:10.1021/OM8000229
22. (h) Q. Yao, Y. Zhang, Angew. Chem. Int. Ed. 2003, 42, 3395. doi:10.1002/ANIE.200351222
23. (i) Q. Yao, M. Sheets, J. Organomet. Chem. 2005, 690, 3577. doi:10.1016/J.JORGANCHEM.2005.03.031
24. G. Liu, B. Wu, J. Zhang, X. Wand, M. Shao, J. Wang, Inorg. Chem. 2009, 48, 2383. doi:10.1021/IC801111H
25. B. Van Berlo, K. Houthoofd, B. F. Sels, P. A. Jacobs, Adv. Synth. Catal. 2008, 350, 1949. doi:10.1002/ADSC.200800211
26. H. Balcar, T. Shinde, N. Zilkova, Z. Bastl, Beilstein J. Org. Chem. 2011, 7, 22. doi:10.3762/BJOC.7.4
27. G. Jas, A. Kirschning, Chem.-Eur. J. 2003, 9, 5708. doi:10.1002/CHEM. 200305212
28. (a) J. Wegner, S. Ceylan, A. Kirschning, Adv. Synth. Catal. 2012, 354, 17. doi:10.1002/ADSC.201100584
29. (b) R. Yuryev, S. Strompen, A. Liese, Beilstein J. Org. Chem. 2011, 7, 1449. doi:10.3762/BJOC.7.169
30. (c) J. Wegner, S. Ceylan, A. Kirschning, Chem. Commun. 2011, 47, 4583. doi:10.1039/C0CC05060A
31. (d) J. P. McMullen, K. F. Jensen, Annu. Rev. Anal. Chem. 2010, 3, 19. doi:10.1146/ANNUREV.ANCHEM.111808.073718
32. (e) J.-I. Yoshida, H. Kim, A. Nagaki, ChemSusChem 2011, 4, 331. doi:10.1002/CSSC.201000271
33. (f) D. Webb, T. F. Jamison, Chem. Sci. 2010, 1, 675. doi:10.1039/ C0SC00381F
34. (g) S. Marre, K. F. Jensen, Chem. Soc. Rev. 2010, 39, 1183. doi:10.1039/B821324K
35. (h) T. Illg, P. Löb, V. Hessel, Bioorg. Med. Chem. 2010, 18, 3707. doi:10.1016/J.BMC.2010.03.073
36. (i) J.-I. Yoshida, Chem. Rec. 2010, 10, 332. doi:10.1002/TCR. 201000020
37. (j) C. G. Frost, L. Mutton, Green Chem. 2010, 12, 1687. doi:10.1039/C0GC00133C
38. (k) X. Y. Mak, P. Laurino, P. H. Seeberger, Beilstein J. Org. Chem. 2009, 5, No. 19. doi:10.3762/BJOC.5.19
39. (l) M. Baumann, I. R. Baxendale, S. V. Ley, Mol. Diversity 2011, 15, 613. doi:10.1007/S11030-010-9282-1
40. (m) C. Wiles, P. Watts, Green Chem. 2012, 14, 38. doi:10.1039/C1GC16022B
41. Complexes M1TM 1a (WO2010/037550A1), M2TM 1b (WO00/15339A1), M22TM 1c (WO2011/117571A1), M31TM 1d (WO00/15339A1), M41TM 1e and M42TM 1f (WO03/062253A1), M51TM 1g (WO2008/034552A1) and M71 SIMESTM 1h (WO2008/065187A1) are subject to patent protection and are available from Umicore AG & Co KG. Terms and conditions are available upon request.
42. Silica gel 60 for column chromatography, 0.040-0.063 mm, pre-dried under high vacuum at 1208C over phosphorus pentoxide for 5 h.
43. A similar observation was reported by H. Clavier, S.P. Nolan, Chem.-Eur. J. 2007, 13, 8029. doi:10.1002/CHEM.200700256
44. M. Bieniek, R. Bujok, M. Cabaj, N. Lugan, G. Lavagne, D. Arlt, K. Grela, J. Am. Chem. Soc. 2006, 128, 13652. doi:10.1021/JA063186W
45. N. T. S. Phan, M. V. der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609. doi:10.1002/ADSC.200505473
46. J. Lim, S. S. Lee, J. Y. Ying, Chem. Commun. 2010, 46, 806. doi:10.1039/B917986K
47. A. Hinchcliffe, C. Hughes, D. A. Pears, M. R. Pitts, Org. Process Res. Dev. 2007, 11, 477. doi:10.1021/OP7000113
48. T. A. Kirkland, R. H. Grubbs, J. Org. Chem. 1997, 62, 7310. doi:10.1021/JO970877P
49. A. Tokuyasu, S. Kunikawa, K. J. McCullough, A. Masuyama, M. Nojima, J. Org. Chem. 2005, 70, 251. doi:10.1021/JO048359J
50. J. A. Bodkin, G. B. Bacskay, M. D. McLeod, Org. Biomol. Chem. 2008, 6, 2544. doi:10.1039/B803310B
51. W. A. Nugent, J. Feldman, J. C. Calabrese, J. Am. Chem. Soc. 1995, 117, 8992. doi:10.1021/JA00140A015
52. D. Rix, F. Caijo, I. Laurent, F. Boeda, H. Clavier, S. P. Nolan, M. Mauduit, J. Org. Chem. 2008, 73, 4225. doi:10.1021/JO800203D
53. A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem.-Eur. J. 2001, 7, 3236. doi:10.1002/1521-3765(20010803)7:15,3236::AID-CHEM3236. 3.0.CO;2-S