| Identification | Back Directory | [Name]
GRUBBS CATALYST 2ND GENERATION | [CAS]
246047-72-3 | [Synonyms]
GRUBBS II
Grubbs Gen 2nd
Grubbs catalyst II
Grubb's II Catalyst
Grubbs Catalyst, 2nd
Grubbs (2nd generation)
Catalyst, 2nd Generation
GRUBBS CATALYST,2 ND GEN
Grubbs2ndgenerationcatalyst
GRUBBS CATALYST 2ND GENERATION
2nd generation Grubbs catalyst
Grubb's second generation catalyst
Grubbs Catalyst 2nd Generation,97+%
Grubbs Catalyst 2nd Generation Grubbs
Grubb's second generation catalyst,97%
Grubbs Catalyst, 2nd Generation
Grubbs Catalyst, 2nd Generation≥ 98% (NMR)
BENZYLIDENE[1,3-DIMESITYL-2-IMIDAZOL.]-C L2-(TRI-CHEX-P)-RU
Tricyclohexylphosphine1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-yli
(1,3-DiMesityliMidazolin-2-ylidene)(tricyclohexylphosphine)rutheniuM dichloride
Benzylidene(dichloro)(1,3-diMesityl-2-iMidazolidinylidene)rutheniuM - tricyclohexylphosphine (1:1)
Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]rut
Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene] dichloro(tricyclohexyl-phosphine) ruthenium
(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)
(1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium ,97%
(1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium ,95%
Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidine]Ruthenium(IV)dichloride
RutheniuM,[1,3-bis(2,4,6-triMethylphenyl)-2-iMidazolidinylidene]dichloro(phenylMethylene)(tricyclohexylphosphine)-,(SP-5-41)-
[1,3-bis(2,4,6-triMethylphenyl)iMidazolidin-2-ylidene](phenylMethylidene)(tricyclohexyl-$l^{5}-phosphanyl)rutheniuMbis(yliuM) dichloride
Grubbs Catalyst, 2nd Generation,(1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium, 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene
1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenylmethylene)(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
Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium
[1
1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenylmethylene)(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 | [EINECS(EC#)]
688-322-3 | [Molecular Formula]
C46H65Cl2N2PRu | [MDL Number]
MFCD03453237 | [MOL File]
246047-72-3.mol | [Molecular Weight]
848.97 |
| Hazard Information | Back Directory | [Chemical Properties]
pink-brown to red-purple crystals or powder | [Uses]
suzuki reaction | [Characteristics]
Grubbs catalyst is a kind of coordination compound used in olefin metathesis reaction, and the ligand in it has a great influence on the catalytic performance and stability of the catalyst. Grubbs second-generation catalysts are more active than first-generation catalysts and have a wider substrate range, including sterically demanding or deactivated olefins such as 1,1-disubstituted olefins and α,β-non- Saturated carbonyl compounds. | [Definition]
Adlhart and Chen found that ligand rotation is the difference between the activity of the first and second-generation Grubbs catalysts. This difference is brought about by a difference in the symmetry of the ligands. The phosphine ligand has a threefold symmetry, which causes a high barrier in the middle of the reaction coordinate, which is forced by the need for rotation of the phosphine. However, the barrier is absent for the second-generation Grubbs catalyst, with twofold symmetry of the NHC ligand. The rate-limiting step for second-generation catalysts is always phosphine dissociation[2]. | [reaction suitability]
reagent type: catalyst
core: ruthenium
reaction type: Ring-Opening Polymerization |
| Questions And Answer | Back Directory | [Description]
Grubbs catalysts are a series of transition metal carbene complexes used as catalyst for olefin metathesis.1 The Grubbs catalysts are based on a ruthenium atom surrounded by five ligands: two neutral electron-donating entities (e.g., trialkylphosphines, N-heterocyclic carbenes), two monoanionic groups (e.g., halides), and one alkylidene moiety (e.g., unsubstituted and substituted methylidenes). L2X2Ru=CHR complexes (where L is a phosphine ligand) were discovered first and are referred to as the first-generation Grubbs catalyst. (L)(L’)X2Ru=CHR complexes (where L is a phosphine ligand and L’ a saturated N-heterocyclic carbene or NHC ligand) are referred to as the second-generation Grubbs catalysts.
The first-generation Grubbs catalysts show attractive functional-group tolerance and handling properties and have been widely used as highly efficient promoters for ring opening metathesis polymerizations, ring-closing metathesis reactions to make disubstituted olefins, ethenolysis (i.e., cleavage of the carbon–carbon double bond), cross-metathesis of terminal olefins, and the preparation of 1,3-dienes via enyne metathesis. These catalysts and analogues are still widely used in important processes, including the ethenolysis of feedstocks derived from bio-renewable seed oils and the manufacture of macrocyclic hepatitis C therapeutics. Nevertheless, the first-generation Grubbs catalysts show limitations with electron-poor and electron-rich double bonds as well as with sterically hindered systems. The second-generation Grubbs catalysts with excellent metathesis activity while retaining the handling characteristics and broad functional-group tolerance of the earlier Grubbs catalysts are thereby developed. At the same time, the second-generation catalysts are stable against moisture and air.
| [Reference]
[1] M. L. Crawley, B. M. Trost, Applications of Transition Metal Catalysis in Drug Discovery and Development, 2012, ISBN 978-0-470-63132-4.
[2] J.I. du Toit, H.C.M. Vosloo, C.G.C.E. van Sittert. “Metal carbenes in homogeneous alkene metathesis: Computational investigations.” Journal of Organometallic Chemistry 738 (2013): Pages 76-91.
[3] Grubbs Catalyst 2nd Generation: Synthesis and Activity of Ruthenium-Based Olefin Metathesis Catalysts. Synfacts 2020; 16(05): 0563. DOI:10.1055/s-0040-1707550
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