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Appearance:pink-brown to red-purple crystals or powder
Purity:99%
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246047-72-3 Name |
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Name |
GRUBBS CATALYST 2ND GENERATION |
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Synonym |
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;(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);Grubbs Catalyst, 2nd;RutheniuM,[1,3-bis(2,4,6-triMethylphenyl)-2-iMidazolidinylidene]dichloro(phenylMethylene)(tricyclohexylphosphine)-,(SP-5-41)-;Grubbs Gen 2nd;Catalyst, 2nd Generation;Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]rut |
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246047-72-3 Chemical & Physical Properties |
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Melting point |
143-149ºC |
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Molecular Formula |
C46H65Cl2N2PRu |
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Molecular Weight |
848.971 |
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PSA |
20.07000 |
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LogP |
13.86190 |
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Exact Mass |
848.330627 |
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Storage condition |
2-8°C |
GRUBBS CATALYST 2ND GENERATION are a series of transition metal carbene complexes used as catalyst for olefin metathesis. 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.
In this study, nano-sized mesoporous carbon-supported HG2 and magnetic γ-Fe2O3 nanoparticles were encapsulated within calcium alginate gels using a one-pot procedure. The HG2 catalyst encapsulated in the alginate/mesoporous carbon matrix exhibited an improved performance in water, and quantitative yields were obtained in ring-closing metathesis reactions of diethyl diallylmalonate even in tap-water under the air atmosphere with no significant ruthenium and iron leaching.
Grubbs and co-workers reported a direct approach towards the preparation of the 4,5- dihydroimidazol-2-ylidene-substituted rutheniumbased catalysts. Compared to their predecessor, these 2nd generation catalysts display higher reactivity, better stability, and improved functional group tolerance.
Grubbs catalyst first generation
1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride
![tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride](/upload/2023/1/58ab0c9e-778a-4257-bfd8-691dd0c5fbf1.png)
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
| Conditions | Yield |
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With KO(C(CH3)3); In hexane; byproducts: KCl, C(CH3)3OH, PCy3; using Schlenk techniques; mixing of (Mes2C3N2H5)(Cl), KO(t-Bu) and (PCy3)2Cl2Ru(CHPh) in anhyd. hexane; degassing of soln. by pulling vac. for afew minutes, heating at 60°C for 24 h in vac. with very vigorous stirring; cooling to room temp., opening the flask to air, addn. of 1:1 2-propanol:water; stirring in air for 30 min, filtration, washing with 2-propanol:water and with hexane, drying under vac. overnight, elem. anal.;
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75% |
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With potassium tert-butylate; In hexane; at 60 ℃; for 24h; Schlenk technique;
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75% |
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With KOC(CH3)3; In toluene; mixing N compd., Ru complex, K compd. in toluene at 50°C;
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Grubbs catalyst first generation
N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
| Conditions | Yield |
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N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 1h; Schlenk technique; Inert atmosphere;
Grubbs catalyst first generation; In benzene; at 80 ℃; for 1.5h; Schlenk technique; Inert atmosphere;
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56% |
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With KO(C(CH3)3); In benzene; byproducts: KBF4, C(CH3)3OH, PCy3; (N2); using Schlenk techniques; mixing of (Mes2C3N2H5)(BF4), KO(t-Bu) and THF; stirring for 1 h; addn. of (PCy3)2Cl2Ru(CHPh) in benzene; heatingat 80°C for 30 min; removal of volatiles under vac., suspending in benzene, filtration over Celite, concn., addn. of methanol, pptn., washing with methanol, pentaneand then drying under vac.;
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45% |
Grubbs catalyst first generation
1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride
1,3-bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine
1,3-di(2,4,6-trimethylphenyl)-2-(pentafluorophenyl)-2,4,5-trihydroimidazole
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