Details

Item Description Structure
Catalog 8337 CAS 246047-72-3
Product Name GRUBBS CATALYST 2ND GENERATION
Other Name Grubb's second generation catalyst;GRUBBS CATALYST 2ND GENERATION;
(1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO
(PHENYLMETHYLENE)(TRICYCLOHEXYLPHOSPHINE)RUTHENIUM;
RUTHENIUM,[1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE]
DICHLORO (PHENYLMETHYLENE) (TRICYCLOHEXYLPHOSPHINE);
Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]
[benzylidene]rut;Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)
-4,5-dihydroimidazol-2-ylidene][benzylidine]Ruthenium(IV)dichloride;
BENZYLIDENE[1,3-DIMESITYL-2-IMIDAZOL.]-C L2-(TRI-CHEX-P)-RU;
Tricyclohexylphosphine1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-yli
Purity 97% ee NA
Molecular Formula C46H65Cl2N2PRu
Molecular Weight 848.97
Color and Form pink-brown to red-purple crystals or powder
Package 5g/10g and more Bulk Ordering Package
Solubility NA
Melting point 143.5-148.5 C(lit.)
Stability Yes
Risk 36/37/38 Safety 26-36/37/39 Hazard NA
spectrometry Conforms to structure
HPLC Conforms to structure
Note Only for research purposes only
Technical Note

Application

Metathesis: Ruthenium-Based Metathesis Catalysts

Catalyst for ring-closing metathesis, cross metathesis and ROMP6 able to produce trisubstituted olefins via cross metathesis,7 and ring closes olefins with excellent functional group tolerance and selectivity.2
Olefin cross metathesis (CM)1 (eq. 1)
Ring closing metathesis (RCM)2 (eq. 2)
Ring opening metathesis (ROM)3 (eq. 3)
Enyne metathesis4 (eq. 4)
Ring-Opening Metathesis Polymerization (ROMP)5 (eq. 5)

1. Synthesis of trisubstituted alkenes via olefin cross-metathesis. Chatterjee, A. K., Grubbs, R. H. Org. Lett. 1, 1751, (1999)
2. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Scholl, M. Org. Lett. 1, 953, (1999)
3. Unusual influence of substituents on ring-opening metathesis reactions. Wright, D. L.; Usher, L. J.; Estrella-Jiminez, M. Org. Lett. 3, 4275, (2001)
4. Expanded scope in ethylene-alkyne cross-metathesis: coordinating heteroatom functionality at the propargylic position. J.A. Smulik, S.T. Diver Org. Lett. 2, 2271, (2000)
5. Highly Efficient Ring-Opening Metathesis Polymerization (ROMP) Using New Ruthenium Catalysts Containing N-Heterocyclic Carbene Ligands C.B. is grateful to the National Science Foundation for a pre-doctoral fellowship. The authors thank Dr. Matthias Scholl for providing catalysts 4 a and 4 c. Bielawski, C. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 39, 2903, (2000)
6. The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story. T.M. Trnka, R.H. Grubbs Acc. Chem. Res. 34, 18, (2001)
7. Org. Lett. 1, 751, (1999)
Olefin-metathesis catalysts for the preparation of molecules and materials (Nobel Lecture). Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 45, 3760, (2006)
Grubbs, R. H. Tetrahedron 60, 7117, (2004)
Scholl, M. Acc. Chem. Res. 1, 953, (1999)
Efficient large-scale synthesis of BILN 2061, a potent HCV protease inhibitor, by a convergent approach based on ring-closing metathesis. J. Org. Chem. 71, 7133, (2006)
Tetrahedron 62, 9017, (2006)
Macrocyclic inhibitors of beta-secretase: functional activity in an animal model. J. Med. Chem. 49, 6147, (2006)

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