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Transition-metal-catalyzed olefin metathesis allows the formation of C–C
bonds, which is one of the most important reactions in organic chemistry.
Grubbs catalysts1 are the reagents of choice for:
• ring-closing metathesis of dienes (RCM)
• ring-opening cross metathesis of olefins (ROCM)
• ring-opening metathesis polymerization (ROMP)
73304
Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium
[Grubbs catalyst 2nd generation]
C46H65Cl2N2PRu Mr 848.98 [246047-72-3] purum, ≥ 97.0% (C) 500mg
New-generation catalyst with increased activity for olefin metathesis reactions; it often gives excellent yields
in cases where the classic Grubbs catalyst fails; 2 even enol ethers undergo ring-closing metathesis (RCM) in
excellent yield in the presence of this catalyst. 3
91501
Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium, polymer-bound
[Grubbs catalyst on polystyrene]
~0.1 mmol/g; cross-linked with 1% DVB; particle size: 100–200 mesh; may contain white polymer
particles (polyethylene) 1g; 5g
This polymer-supported Grubbs catalyst can be recovered from the reaction mixture after the reaction is
completed and reused; this saves resources and avoids metal contamination of metathesis products, which is
a serious problem in pharmaceutical chemistry. 4
09587
Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium
[Grubbs catalyst]
C43H72Cl2P2Ru Mr 822.97 [172222-30-9] purum, ≥ 97.0% (C) 250mg; 1g; 5g
Highly active and functional-group-tolerant catalyst for metathesis reactions, 5 in particular ring-closing of
dienes to macrocycles 6 or ring-opening polymerization. 7 It is also the reagent used in preparing immobilized,
2nd generation Grubbs catalysts. 8
(1) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (2)(a) Chatterjee, A. K. et al. J. Am. Chem. Soc. 2000, 122, 3783. (b) Scholl, M. et al. Org. Lett. 1999, 1, 953.
(c) Efremov, I.; Paquette, L. A. J. Am. Chem. Soc. 2000, 122, 9324. (d) Sprott, K. T. et al. Synthesis 2001, 612. (e) Ravn, J.; Nielsen, P. J. Chem. Soc., Perkin Trans 1 2001, 985.
(f) Skaanderup, P. R.; Madsen, R. Chem. Commun. 2001, 1106. (3) Rainier, J. D. et al. Tetrahedron Lett. 2001, 42, 179. (4) Ahmed, M. et al. ibid. 1999, 40, 8657. (5) Schwab,
P. et al. J. Am. Chem. Soc. 1996, 118, 100. (6)(a) Miller, S. J. et al. ibid. 1996, 118, 9606. (b) Fürstner, A.; Langemann, K. ibid. 1997, 119, 9130. (7) Morita, T. et al.
Macromolecules 2000, 33, 6621. (8) Schürer, S. C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 3898.
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