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569747 Aldrich

Grubbs Catalyst, 2nd Generation

Synonym: (1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium, Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium, [1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium

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Description

Frequently Asked Questions

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Application

Metathesis: Ruthenium-Based Metathesis Catalysts

Catalyst for ring-closing metathesis, cross metathesis and ROMP1 able to produce trisubstituted olefins via cross metathesis,8 and ring closes olefins with excellent functional group tolerance and selectivity.9

Grubbs 2nd Generation Catalyst

Generally more active compared to 1st generation catalysts and with a broader substrate scope, including sterically demanding or deactivated olefins such as 1,1-disubstituted olefins and α,β-unsaturated carbonyls.1,2,3,4,5,6,7

Other Notes

NO BULK ORDERS

Packaging

100, 500 mg in glass bottle

2 g in glass bottle

Legal Information

US Patent No. 6,111,121 and 7,329,758 (and associated foreign equivalents of the foregoing) apply. Sale of this product conveys to the buyer a limited-use research license. For full details of this license please see sigma-aldrich.com/materialicense. For questions, please contact us at aldrich@sial.com or Materia at info@materia-inc.com.

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Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
F
Risk Statements (Europe) 
11
RIDADR 
UN 1325 4.1 / PGII
WGK Germany 
3

Protocols & Articles

Articles

Enyne Metathesis

Enyne metathesis has emerged as a powerful method for the synthesis of conjugated dienes.1 Botta and coworkers utilized a similar approach, where the olefin was replaced with an enol ether. Reaction ...
William Sommer
Aldrich ChemFiles 2009, 9.6, 7.
Keywords: Chemfiles, Enyne metathesis, Metathesis, Microwave synthesis

Ring-Closing Metathesis

Ring-closing metathesis has become an essential tool for C-C bond formation as demonstrated by the profound impact on total synthesis in recent years.1 The first examples date back to 1980 and involv...
William Sommer
Aldrich ChemFiles 2009,9.6, 4.
Keywords: C-C bond formation, Chemfiles, Cyclizations, Metathesis, Ring-closing metathesis

Ruthenium-Based Metathesis Catalysts

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-metat...
ChemFiles Volume 4 Article 2
Keywords: Aldrichimica Acta, Cross metathesis, Metathesis, Organic synthesis, Ring opening metathesis polymerisation, Ring-closing metathesis

Synthesis of Furans

Donohoe and co-workers have developed several synthetic approaches to the synthesis of furans which incorporate RCM as a key step.1 In 2007, the researchers synthesized a series of di- and tri-substi...
William Sommer
Aldrich ChemFiles 2009,9.6, 5.
Keywords: Anti-inflammatory agents, Chemfiles

Protocols

Olefin Metathesis in Water at Room Temperature using TPGS-750-M

TPGS-750-M, DL-α-Tocopherol methoxypolyethylene glycol succinate, is a designer surfactant composed of a lipophilic α-tocopherol moiety and a hydrophilic PEG-750-M chain, joined by an inexpensive suc...

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions

TPGS-750-M, DL-α-Tocopherol methoxypolyethylene glycol succinate, is a designer surfactant composed of a lipophilic α-tocopherol moiety and a hydrophilic PEG-750-M chain, joined by an inexpensive suc...
Keywords: Aminations, Buchwald-Hartwig amination, Catalysis, Chromatography, Coupling reactions, Cross couplings, Environmental, Evaporation, Flash chromatography, Heck Reaction, Ligands, Metathesis, Olefin metathesis

Related Content

Metathesis in Chemical Synthesis

Olefin metathesis is now a well-entrenched synthetic technique, and is a powerful method for the clean construction of innumerable classes of chemical architectures. The broadly accepted belief that ...
Keywords: Aldrichimica Acta, Applications, Building blocks, Cross metathesis, Enyne metathesis, Exothermic, Isomerizations, Ligands, Living polymerization, Metathesis, Methods, Olefin metathesis, Organic synthesis, Polymerization reactions, Ring opening metathesis polymerisation, Ring-closing metathesis, Type

Peer-Reviewed Papers

References

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1. The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story. T.M. Trnka, R.H. Grubbs Acc. Chem. Res. 34, 18, (2001)

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2. Grubbs, R. H. Tetrahedron 60, 7117, (2004)

3. Schrodi, Y.; Pederson, R. L. Aldrichimica Acta 40th ed.,, 45, (2007)

4. Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts. Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 110, 1746, (2010)

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5. Olefin Metathesis and Beyond A list of abbreviations can be found at the end of this article. Fürstner, A. Angew. Chem. Int. Ed. Engl. 39, 3012, (2000)

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6. Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. Engl. 36th ed.,, 2036, (1997)

7. Ritter, T., et al. Organometallics 25th ed.,, 5740, (2006)

8. Org. Lett. 1, 751, (1999)

9. 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)

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Macrocyclic inhibitors of beta-secretase: functional activity in an animal model. J. Med. Chem. 49, 6147, (2006)

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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)

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Scholl, M. Acc. Chem. Res. 1, 953, (1999)

Tetrahedron 62, 9017, (2006)

Synthesis of trisubstituted alkenes via olefin cross-metathesis. Chatterjee, A. K., Grubbs, R. H. Org. Lett. 1, 1751, (1999)

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Synthesis of trisubstituted alkenes via olefin cross-metathesis. Chatterjee, A. K., Grubbs, R. H. Org. Lett. 1, 1751, (1999)

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Olefin-metathesis catalysts for the preparation of molecules and materials (Nobel Lecture). Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 45, 3760, (2006)

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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)

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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)

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Unusual influence of substituents on ring-opening metathesis reactions. Wright, D. L.; Usher, L. J.; Estrella-Jiminez, M. Org. Lett. 3, 4275, (2001)

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