Ruthenium-Based Metathesis Catalysts

ChemFiles Volume 4 Article 2

Sigma-Aldrich is pleased to announce an agreement with Materia, Inc. to exclusively distribute research quantities of Grubbs catalysts and Hoveyda–Grubbs catalysts. For a recent review on cross-metathesis of nitrogen-containing systems and for pertinent references to other systems, see Aldrichimica Acta, 2003, 36(3), 93.

Grubbs Catalyst 1st Generation

The first metathesis catalyst to be widely utilized in organic synthesis, Grubbs First Generation Catalyst effects ring-closing metathesis, olefin cross-metathesis, and ROMP with high activities and tolerance for functional groups and protic media.1,2

Grubbs Catalyst 2nd Generation

Grubbs Second Generation Catalyst is a more active analog of the first-generation Grubbs catalyst for ring-closing metathesis, cross metathesis, and ROMP,3 and can lead to trisubstituted olefins via cross metathesis;4 it ring-closes olefins with excellent functionalgroup tolerance and selectivity.5

Dichloro(3-methyl-2-butenylidene)bis(tricyclopentylphosphine) ruthenium(II)

Hoveyda–Grubbs Catalyst 1st Generation

An efficient, recyclable catalyst for RCM of terminal olefins.6,7

Hoveyda–Grubbs Catalyst 2nd Generation

The Hoveyda–Grubbs Second Generation catalyst shows efficiencies similar to those of second-generation Grubbs catalyst, but with different substrate specificities. The catalyst is unique in catalyzing the ring-closing, ring-opening, and cross-metathesis reactions of highly electron-deficient substrates.7,8

Dichloro(3-methyl-2-butenylidene)bis(tricyclohexylphosphine) ruthenium(II)

Materials

     

References

  1. Schwab, P. et al. J. Am. Chem. Soc. 1996, 118, 100.
  2. Miller, S. J. et al. ibid. 1996, 118, 9606.
  3. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
  4. Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751.
  5. (a) Scholl, M. et al. ibid. 1999, 1, 953. (b) Saito, N. et al. ibid. 2002, 4, 803.
  6. Kingsbury, J. S. et al. J. Am. Chem. Soc. 1999, 121, 791.
  7. Garber, S. B. et al. ibid. 2000, 122, 8168.
  8. Randl, S. et al. Synlett 2001, 430.

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