Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

12 Issues per year


IMPACT FACTOR 2016: 2.626
5-year IMPACT FACTOR: 3.210

CiteScore 2016: 2.45

SCImago Journal Rank (SJR) 2016: 0.972
Source Normalized Impact per Paper (SNIP) 2016: 1.049

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 81, Issue 11 (Oct 2009)

Issues

Onium-tagged Ru complexes as universal catalysts for olefin metathesis reactions in various media

Łukasz Gułajski
  • Corresponding author
  • Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Marc Mauduit
  • Corresponding author
  • “Sciences Chimiques de Rennes”, École Nationale Supérieure de Chimie de Rennes CNRS, UMR 6226 Université Européenne de Bretagne Avenue du Général Leclerc, CS 50837 35708 Rennes Cedex 7, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Karol Grela
  • Corresponding author
  • Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-10-30 | DOI: https://doi.org/10.1351/PAC-CON-08-10-13

Polar olefin metathesis catalysts bearing a pendant electron-withdrawing (EWG) onium group are reviewed. The presence of this group not only activates the catalysts electronically, but renders them more hydrophilic. Catalysts can, therefore, be efficiently used not only in traditional media such as methylene chloride and toluene, but also in technical-grade alcohols, alcohol–water mixtures, and in neat water. In addition, some onium-tagged catalysts can act as inisurfs (initiator + surfactant molecules), promoting metathesis under heterogeneous aqueous conditions. Finally, some of these catalysts can be used in ionic liquids. Various ring-closing-, cross- and enyne metathesis reactions were conducted with these catalysts.

Keywords: aqueous media; catalysis; ionic liquids; olefin metathesis; ruthenium; sustainable chemistry

Conference

International Conference on Green Chemistry (ICGC-2), IUPAC International Conference on Green Chemistry, ICGC, Green Chemistry , 2nd, Moscow, Russia, 2008-09-14–2008-09-20

References

  • 1a

    , R. R. Schrock, A. H. Hoveyda. Angew. Chem., Int. Ed. 42, 4592 (2003).CrossrefGoogle Scholar

  • 1b

    , T. M. Trnka, R. H. Grubbs. Acc. Chem. Res. 34, 18 (2001).CrossrefGoogle Scholar

  • 1c

    , A. Fürstner. Angew. Chem., Int. Ed. 39, 3012 (2000).CrossrefGoogle Scholar

  • 1d

    , R. H. Grubbs, S. Chang. Tetrahedron 54, 4413 (1998).CrossrefGoogle Scholar

  • 1e

    , M. Schuster, S. Blechert. Angew. Chem., Int. Ed. Engl. 36, 2037 (1997).CrossrefGoogle Scholar

  • 1f

    V. Dragutan, I. Dragutan, A. T. Balaban. Platinum Met. Rev. 45, 155 (2001).Google Scholar

  • 2

    , T. Nicola, M. Brenner, K. Donsbach, P. Kreye. Org. Process Res. Dev. 9, 513 (2005).CrossrefGoogle Scholar

  • 3a

    , J. C. Conrad, H. H. Parnas, J. L. Snelgrove, D. E. Fogg. J. Am. Chem. Soc. 127, 11882 (2005).CrossrefGoogle Scholar

  • 3b

    , For example, in a crude untreated product of diethyl diallylmalonate RCM catalyzed by 5 mol % of Grubbs I-generation catalyst, the theoretical amount of Ru is 90 mg per 5 mg of product (18 000 ppm). After filtration of the crude reaction mixture, the Ru level was reduced to 59.7 ± 0.50 mg per 5 mg (12 000 ppm). Further purification of such crude metathesis products usually reduces Ru levels below 2000 ppm, see ref. [3a] and (b) K. McEleney, D. P. Allen, A. E. Holliday, C. M. Crudden. Org. Lett. 8, 2663 (2006).CrossrefGoogle Scholar

  • 4

    Another solution to this problem might be based on the immobilization of a metathesis catalyst in a separate liquid or solid phase. For recent reviews, see.Google Scholar

  • 4a

    , A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity. Org. Biomol. Chem. 2, 1 (2004).CrossrefGoogle Scholar

  • 4b

    , R. M. Buchmeiser. New J. Chem. 28, 549 (2004); for related systems developed in our laboratories, see.CrossrefGoogle Scholar

  • 4c

    K. Grela, K. Mennecke, U. Kunz, A. Kirschning. Synlett 2948 (2005).Google Scholar

  • 4d

    , K. Grela, M. Tryznowki, M. Bieniek. Tetrahedron Lett. 43, 6425 (2002).CrossrefGoogle Scholar

  • 5

    , J. H. Cho, B. M. Kim. Org. Lett. 5, 531 (2003).CrossrefGoogle Scholar

  • 6

    B. Cornils, W. A. Hermann (Eds.). Aqueous-Phase Organometallic Catalysis, Wiley-VCH, Weinheim (2004).Google Scholar

  • 7

    , For a review on sustainable aspects of olefin metathesis, see: H. Clavier, K. Grela, A. Kirschning, M. Mauduit, S. P. Nolan. Angew. Chem., Int. Ed. 46, 6786 (2007).CrossrefGoogle Scholar

  • 8

    For example, see.Google Scholar

  • 8a

    , E. J. Gordon, W. J. Sanders, L. L. Kiessling. Nature 392, 30 (1998).CrossrefGoogle Scholar

  • 8b

    , M. Kanai, K. H. Mortell, L. L. Kiessling. J. Am. Chem. Soc. 119, 9931 (1997).CrossrefGoogle Scholar

  • 8c

    , D. D. Manning, X. Hu, P. Beck, L. L. Kiessling. J. Am. Chem. Soc. 119, 3161 (1997).CrossrefGoogle Scholar

  • 8d

    , D. D. Manning, L. E. Strong, X. Hu, P. Beck, L. L. Kiessling. Tetrahedron 53, 11937 (1997).CrossrefGoogle Scholar

  • 9a

    , D. M. Lynn, S. Kanaoka, R. H. Grubbs. J. Am. Chem. Soc. 118, 784 (1996).CrossrefGoogle Scholar

  • 9b

    , V. Monteil, P. Wehrmann, S. Mecking. J. Am. Chem. Soc. 127, 14568 (2005).CrossrefGoogle Scholar

  • 10a

    , T. A. Kirkland, D. M. Lynn, R. H. Grubbs. J. Org. Chem. 63, 9904 (1998).CrossrefGoogle Scholar

  • 10b

    , K. J. Davis, D. Sinou. J. Mol. Catal. A: Chem. 177, 173 (2002).CrossrefGoogle Scholar

  • 10c

    , M. T. Mwangi, M. B. Runge, N. B. Bowden. J. Am. Chem. Soc. 128, 14434 (2006).CrossrefGoogle Scholar

  • 10d

    , S. J. Connon, M. Rivard, M. Zaja, S. Blechert. Adv. Synth. Catal. 345, 572 (2003).CrossrefGoogle Scholar

  • 10e

    , M. T. Zarka, O. Nuyken, R. Weberskirch. Macromol. Rapid Commun. 25, 858 (2004).CrossrefGoogle Scholar

  • 10f

    , for early examples of ROMP in aqueous media initiated by poorly defined Ru complexes such as RuCl3(H2O)n or Ru(H2O)6(TsO)2, see: B. M. Novak, R. H. Grubbs. J. Am. Chem. Soc. 110, 960 (1988).CrossrefGoogle Scholar

  • 10g

    , B. M. Novak, R. H. Grubbs. J. Am. Chem. Soc. 110, 7542 (1988).CrossrefGoogle Scholar

  • 10h

    , M. A. Hillmeyer, C. Lepetit, D. V. McGrath, B. M. Novak, R. H. Grubbs. Macromolecules 25, 3345 (1992).CrossrefGoogle Scholar

  • 10i

    , K. H. Mortell, R. V. Weatherman, L. L. Kiessling. J. Am. Chem. Soc. 118, 2297 (1996).CrossrefGoogle Scholar

  • 10j

    , B. H. Lipshutz, G. T. Aguinaldo, S. Ghorai, K. Voigtritter. Org. Lett. 10, 1325 (2008).CrossrefGoogle Scholar

  • 10k

    , B. H. Lipshutz, S. Ghorai, G. T. Aguinaldo. Adv. Synth. Catal. 7–8, 953 (2008).CrossrefGoogle Scholar

  • 10l

    , for a review on aqueous olefin metathesis, see: D. Burtscher, K. Grela. Angew. Chem., Int. Ed. 48, 442 (2009).CrossrefGoogle Scholar

  • 11a

    , K. Grela, S. Harutyunyan, A. Michrowska. Angew. Chem., Int. Ed. 41, 4038 (2002).CrossrefGoogle Scholar

  • 11b

    , A. Michrowska, R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, K. Grela. J. Am. Chem. Soc. 126, 9318 (2004).CrossrefGoogle Scholar

  • 12a

    , K. Grela, A. Michrowska, M. Bieniek. Chem. Rec. 6, 144 (2006).CrossrefGoogle Scholar

  • 12b

    , A. Michrowska, K. Grela. Pure Appl. Chem. 80, 31 (2008).CrossrefGoogle Scholar

  • 13

    Ł. Gułajski, A. Michrowska, R. Bujok, K. Grela. J. Mol. Catal. A: Chem. 348, 931 (2006).Google Scholar

  • 14

    , A. Michrowska, K. Mennecke, U. Kunz, A. Kirschning, K. Grela. J. Am. Chem. Soc. 128, 13261 (2006).CrossrefGoogle Scholar

  • 15

    , A. Kirschning, K. Harmrolfs, K. Mennecke, J. Messinger, U. Schön, K. Grela. Tetrahedron Lett. 49, 3019 (2008).CrossrefGoogle Scholar

  • 16

    A. Michrowska. PhD Thesis, Institute of Organic Chemistry, Warsaw (2006).Google Scholar

  • 17

    A. Michrowska, Ł. Gułajski, K. Grela. Chem. Today 24 (6), 19 (2006).Google Scholar

  • 18

    , A. Michrowska, Ł. Gułajski, Z. Kaczmarska, K. Mennecke, A. Kirschning, K. Grela. Green Chem. 8, 685 (2006).CrossrefGoogle Scholar

  • 19

    , Ł. Gułajski, A. Michrowska, J. Naro?nik, Z. Kaczmarska, L. Rupnicki, K. Grela. ChemSusChem 1, 103 (2008).CrossrefGoogle Scholar

  • 20

    , J. B. Binder, I. A. Guzei, R. T. Raines. Adv. Synth. Catal. 349, 395 (2007).CrossrefGoogle Scholar

  • 21a

    , D. Rix, H. Clavier, Ł. Gułajski, K. Grela, M. Mauduit. J. Organomet. Chem. 691, 5397 (2006).CrossrefGoogle Scholar

  • 21b

    , D. Rix, F. Caïjo, I. Laurent, Ł. Gułajski, K. Grela, M. Mauduit. Chem. Commun. 3771 (2007).CrossrefGoogle Scholar

  • 22

    , J. P. Jordan, R. H. Grubbs. Angew. Chem., Int. Ed. 46, 5152 (2007).CrossrefGoogle Scholar

  • 23

    , A. Kirschning, Ł. Gułajski, K. Mennecke, A. Meyer, T. Busch, K. Grela. Synlett 2692 (2008).CrossrefGoogle Scholar

  • 24

    , J. S. Kingsbury, S. B. Garber, J. M. Giftos, B. L. Gray, M. M Okamoto, R. A. Farrer, J. T. Fourkas, A. H. Hoveyda. Angew. Chem., Int. Ed. 40, 4251 (2001).CrossrefGoogle Scholar

  • 25

    E. Chomiszczak, Ł. Gułajski, K. Grela. Unpublished results.Google Scholar

  • 26

    , P. Sledź, M. Mauduit, K. Grela. Chem. Soc. Rev. 37, 2433 (2008).CrossrefGoogle Scholar

About the article

Published Online: 2009-10-30

Published in Print: 2009-10-31


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-08-10-13.

Export Citation

© 2013 Walter de Gruyter GmbH, Berlin/Boston. Copyright Clearance Center

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Sandra Hübner, Johannes G. de Vries, and Vittorio Farina
Advanced Synthesis & Catalysis, 2016, Volume 358, Number 1, Page 3
[2]
Houssein Nasrallah, Anastassiya Pagnoux, Dorian Didier, Caroline Magnier, Loïc Toupet, Régis Guillot, Christophe Crévisy, Marc Mauduit, and Emmanuelle Schulz
European Journal of Organic Chemistry, 2014, Volume 2014, Number 35, Page 7781
[3]
Nathalie Clousier, Alexandra Filippi, Etienne Borré, Eric Guibal, Christophe Crévisy, Fréderic Caijo, Marc Mauduit, Isabelle Dez, and Annie-Claude Gaumont
ChemSusChem, 2014, Volume 7, Number 4, Page 1040
[4]
Wioletta Kośnik and Karol Grela
Dalton Transactions, 2013, Volume 42, Number 20, Page 7463
[5]
Wladimir Solodenko, Angelino Doppiu, René Frankfurter, Carla Vogt, and Andreas Kirschning
Australian Journal of Chemistry, 2013, Volume 66, Number 2, Page 183
[6]
Etienne Borré, Mathieu Rouen, Isabelle Laurent, Magaly Magrez, Fréderic Caijo, Christophe Crévisy, Wladimir Solodenko, Loic Toupet, René Frankfurter, Carla Vogt, Andreas Kirschning, and Marc Mauduit
Chemistry - A European Journal, 2012, Volume 18, Number 51, Page 16369
[7]
Pedro Merino, Tomas Tejero, Graziella Greco, Eduardo Marca, Ignacio Delso, Asier Gómez-SanJuan, and Rosa Matute
HETEROCYCLES, 2012, Volume 84, Number 1, Page 75
[8]
James W. Herndon
Coordination Chemistry Reviews, 2011, Volume 255, Number 1-2, Page 3

Comments (0)

Please log in or register to comment.
Log in