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Topics in Catalysis

, Volume 57, Issue 17–20, pp 1351–1358 | Cite as

Synthesis Optimization and Catalytic Activity Screening of Industrially Relevant Ruthenium-Based Metathesis Catalysts

  • Angelino DoppiuEmail author
  • Frederic Caijo
  • Fabien Tripoteau
  • Savinien Bompard
  • Christophe Crévisy
  • Marc Mauduit
Original Paper

Abstract

Olefin metathesis is a powerful catalytic reaction that has a huge potential in the pharmaceutical, polymer and specialty chemicals industries. Cost-effective industrial applications require large-scale availability of catalyst precursors which combine high activity, high selectivity and long life-time. Among the known numerous families of olefin metathesis catalysts, the Umicore M7-catalyst family represents a novel class of Hoveyda-type complexes showing excellent chemical stabilities and modular activity profiles. Relevant aspects related to their industrial synthesis as well as their catalytic performance in valuable olefin metathesis transformations are overviewed here.

Keywords

Olefin metathesis Ruthenium Industrial catalyst synthesis Terpenes Fragrances Fatty esters 

Notes

Acknowledgments

Funding for this project was partially provided by the Agence Nationale de la Recherche (Project CFLOW-OMANR-2012-CDII-0002, Grant to S.B.) and by Rennes-Métropole. M.M. and F.C. thank the Region Bretagne for its financial support (Fonds de Maturation Feder N° 09005612).

References

  1. 1.
    Grubbs RH (ed) (2003) Handbook of Metathesis. Wiley-VCH, WeinheimGoogle Scholar
  2. 2.
    Vougioukalakis GC, Grubbs RH (2010) Chem Rev 110:1746CrossRefGoogle Scholar
  3. 3.
    Clavier H, Grela K, Kirschning A, Mauduit M, Nolan SP (2007) Angew Chem Int Ed 46:6786CrossRefGoogle Scholar
  4. 4.
    Briel O, Cazin CSJ (2010) In: Cazin CSJ (ed) N-heterocycle carbenes in transition metal catalysis and organocatalysis. Springer, LondonGoogle Scholar
  5. 5.
    Chikkali S, Mecking S (2012) Angew Chem Int Ed 51:5802CrossRefGoogle Scholar
  6. 6.
    Fürstner A (2011) Chem Commun 47:6505CrossRefGoogle Scholar
  7. 7.
    Samojlowicz C, Bieniek M, Grela K (2009) Chem Rev 109:3708CrossRefGoogle Scholar
  8. 8.
    Love JAJ, Morgan P, Trnka TM, Grubbs RH (2002) Angew Chem Int Ed 41:4035CrossRefGoogle Scholar
  9. 9.
    Wakamatsu H, Blechert S (2002) Angew Chem Int Ed 41:2403CrossRefGoogle Scholar
  10. 10.
    Grela K, Harutyunyan S, Michrowska A (2002) Angew Chem Int Ed 41:4038CrossRefGoogle Scholar
  11. 11.
    Zaja M, Connon SJ, Dunne AM, Rivard M, Buschmann N, Jiricek J, Blechert S (2003) Tetrahedron 59:6545CrossRefGoogle Scholar
  12. 12.
    Romero PE, Piers WE, McDonald R (2004) Angew Chem Int Ed 43:6161CrossRefGoogle Scholar
  13. 13.
    Zhan Z-YJ (2007) WO2007/003135Google Scholar
  14. 14.
    Nelson DJ, Queval P, Rouen M, Magrez M, Toupet L, Caijo F, Borré E, Laurent I, Crévisy C, Baslé O, Mauduit M, Percy JM (2013) ACS Catalysis 3:259CrossRefGoogle Scholar
  15. 15.
    Gatti M, Vieille-Petit L, Luan X, Mariz R, Drinkel E, Linden A, Dorta R (2009) J Am Chem Soc 131:9498CrossRefGoogle Scholar
  16. 16.
    Vorfalt T, Leuthäußer S, Plenio H (2009) Angew Chem Int Ed 48:5191CrossRefGoogle Scholar
  17. 17.
    Kuhn KM, Champagne TM, Hong SH, Wei W-H, Nickel A, Lee CW, Virgil SC, Grubbs RH, Pederson RL (2010) Org Lett 12:984CrossRefGoogle Scholar
  18. 18.
    Sashuk V, Peeck LH, Plenio H (2010) Chem Eur J 16:3983CrossRefGoogle Scholar
  19. 19.
    Bantreil X, Randall RAM, Slawin AMZ, Nolan SP (2010) Organometallics 29:3007CrossRefGoogle Scholar
  20. 20.
    Songis O, Slawin AMZ, Cazin CSJ (2012) Chem Commun 48:1266CrossRefGoogle Scholar
  21. 21.
    Seiders TJ, Ward DW, Grubbs RH (2001) Org Lett 3:3225CrossRefGoogle Scholar
  22. 22.
    Funk TW, Berlin JM, Grubbs RH (2006) J Am Chem Soc 128:1840CrossRefGoogle Scholar
  23. 23.
    Van Veldhuizn JJ, Garber SB, Kingsbury JS, Hoveyda AH (2002) J Am Chem Soc 124:4954CrossRefGoogle Scholar
  24. 24.
    Grandbois SK (2008) Collins. Chem Eur J 14:9323CrossRefGoogle Scholar
  25. 25.
    Khan RKM, Zhugralin AR, Torker S, O’Brien RV, Lombardi PJ, Hoveyda AH (2012) J Am Chem Soc 134:12438CrossRefGoogle Scholar
  26. 26.
    Ibrahem I, Yu M, Schrock RR, Hoveyda AH (2009) J Am Chem Soc 131:3844CrossRefGoogle Scholar
  27. 27.
    Flook MM, Jiang AJ, Schrock RR, Müller P, Hoveyda AH (2009) J Am Chem Soc 131:7962CrossRefGoogle Scholar
  28. 28.
    Peryshkov DV, Schrock RR, Takase MK, Müller P, Hoveyda AH (2011) J Am Chem Soc 133:20754CrossRefGoogle Scholar
  29. 29.
    Endo K, Grubbs RH (2011) J Am Chem Soc 133:8525CrossRefGoogle Scholar
  30. 30.
    Keitz BK, Endo K, Patel PR, Herbert MB, Grubbs RH (2012) J Am Chem Soc 134:693CrossRefGoogle Scholar
  31. 31.
    Vougioukalakis GC (2012) Chem Eur J 18:8868CrossRefGoogle Scholar
  32. 32.
    Mauduit M, Laurent I, Clavier H (2008) Ruthenium carbene chelate complexes as thermally stable and active catalysts for alkene metathesis. PCT Int Appl WO2008/065187; Umicore M7 catalysts are subject to WO2008/065187A1 and available from Umicore AG & Co. KG. Terms and conditions upon requestGoogle Scholar
  33. 33.
    Rix D, Caijo F, Laurent I, Boeda F, Clavier H, Nolan SP, Mauduit M (2008) J Org Chem 73:4225CrossRefGoogle Scholar
  34. 34.
    Clavier H, Caijo F, Borré E, Rix D, Boeda F, Nolan SP, Mauduit M (2009) Eur J Org Chem 25:4254CrossRefGoogle Scholar
  35. 35.
    Borré E, Pieck C, Caijo F, Crévisy C, Mauduit M (2009) Chim Oggi 27:74Google Scholar
  36. 36.
    Mol JC (2004) Tops Catal 27:97CrossRefGoogle Scholar
  37. 37.
    Chikkali S, Mecking S (2012) Angew Chem Int Ed 51:5802CrossRefGoogle Scholar
  38. 38.
    Mohapatra DK, Somaiah R, Rao MM, Caijo F, Mauduit M, Yadav JS (2010) Synlett 1223Google Scholar
  39. 39.
    Borré E, Dinh TH, Caijo F, Crévisy C, Mauduit M (2011) Synthesis 2125Google Scholar
  40. 40.
    Caijo F, Tripoteau F, Bellec A, Crévisy C, Basle O, Mauduit M, Briel O (2013) Catal. Sci. Technol. 3:429Google Scholar
  41. 41.
    Boufroura H, Mauduit M, Drège E, Joseph D (2013) J Org Chem 78:2346CrossRefGoogle Scholar
  42. 42.
    Garber SB, Kingsbury JS, Gray BL, Hoveyda AH (2000) J Am Chem Soc 122:8168CrossRefGoogle Scholar
  43. 43.
    Gessler S, Randl S, Blechert S (2000) Tetrahedron Lett 41:9973CrossRefGoogle Scholar
  44. 44.
    Urbina-Blanco CA, Manzini S, Pérez Gomes J, Doppiu A, Nolan SP (2011) Chem Commun 47:5022. Umicore M20 and M23 catalysts are available from Umicore AG & Co. KG. Terms and conditions upon requestGoogle Scholar
  45. 45.
    Rivero-Cruz JF, Garcia-Aguirre G, Cerda-Garcia-Rojas CM, Mata R (2000) Tetrahedron 56:5337CrossRefGoogle Scholar
  46. 46.
    Fürstner A, Radkowski K (2001) Chem Commun 671Google Scholar
  47. 47.
    Fürstner K, Radkowski C, Wirtz R, Goddard WC, Lehmann R Mynott (2002) J Am Chem Soc 124:7061CrossRefGoogle Scholar
  48. 48.
    Yuzikhin O, Metino G, Berestetskiy A (2007) J Agric Food Chem 55:7707CrossRefGoogle Scholar
  49. 49.
    Hattori T, Suzuki Y, Uesugi O, Oi S, Miyano S (2000) Chem Commun 73Google Scholar
  50. 50.
    Hattori T, Suzuki Y, Ito Y, Hotta D, Miyano S (2002) Tetrahedron 58:5215CrossRefGoogle Scholar
  51. 51.
    Alchihab M, Destain J, Aguedo M, Thonart P (2010) Biotechnol Agron Soc Environ 14:681Google Scholar
  52. 52.
    Williams AS (1999) Synthesis 1707Google Scholar
  53. 53.
    Fürstner A, Langemann K (1997) Synthesis 792Google Scholar
  54. 54.
    Hagiwara H, Nakamura T, Okunaka N, Hoshi T, Suzuki T (2010) Helv Chim Acta 93:175CrossRefGoogle Scholar
  55. 55.
    Choi TL, Chattterjee AK, Grubbs RH (2001) Angew Chem Int Ed 40:1277CrossRefGoogle Scholar
  56. 56.
    Buchanan MS, Carroll AR, Fechner GA, Boyle A, Simpson M, Addepalli R, Avery VM, Hooper JNA, Cheung T, Chen H, Quinn RJ (2008) J Nat Prod 71:1066CrossRefGoogle Scholar
  57. 57.
    Ullah N, Arafeh KM (2009) Tetrahedron Lett 50:158CrossRefGoogle Scholar
  58. 58.
    Erb W, Payet E (2010) L’Actualité Chimique 345:33Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Angelino Doppiu
    • 1
    Email author
  • Frederic Caijo
    • 2
  • Fabien Tripoteau
    • 2
  • Savinien Bompard
    • 3
  • Christophe Crévisy
    • 3
  • Marc Mauduit
    • 3
  1. 1.Precious Metals ChemistryUmicore AG & Co. KGHanauGermany
  2. 2.OMEGA CAT SYSTEM SarlEcole Nationale Supérieure de Chimie de RennesRennes Cedex 7France
  3. 3.CNRS, UMR 6226Ecole Nationale Supérieure de Chimie de RennesRennes Cedex 7France

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