(1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)RUTHENIUM

Base Information

• Chemical Name: (1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)RUTHENIUM
• CAS No.: 301224-40-8
• Molecular Formula: C31H38Cl2N2ORu
• Molecular Weight: 627.639
• Hs Code.: 2933990090
• Mol file: 301224-40-8.mol

Synonyms:(1,3-Dimesityl-2-imidazolidinylidene)(o-isopropoxyphenylmethylene)rutheniumdichloride;Grubbs-Hoveyda catalyst;Hoveyda II catalyst;Hoveyda catalyst;Hoveyda-Grubbs catalyst;Hoveyda-Grubbs catalyst 2nd. generation;Hoveyda-Grubbs second generation catalyst;Second-generation Hoveyda catalyst;[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(o-isopropoxyphenylmethylene)ruthenium;[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro[[2-(1-methylethoxy-kO)phenyl]methylene-kC]ruthenium;

Chemical Property of (1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)RUTHENIUM

Chemical Property:

• Melting Point: 216-220 °C(lit.)
• PSA: 15.71000
• LogP: 8.18270
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]Dichloro(o-isopropoxyphenylmethylene)ruthenium ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: It′s a phosphine free version of Grubbs 2nd Generation Catalyst with comparable reactivity, but initiates more readily at lower temperatures. Efficient for metathesis of electron-deficient substrates including fluorinated olefins. Demonstrated in multiple large-scale pharmaceutical applications.It can be used as a catalyst for olefin cross-metathesis with fluorinated olefins (CM), ring-closing metathesis (RCM), ring-opening metathesis (ROM), and a sequence of a metathesis reaction and subsequent dihydroxylation of the newly formed double bond.

Technology Process of (1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)RUTHENIUM

There total 52 articles about (1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)RUTHENIUM which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Hoveyda-Grubbs catalyst first generation + 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene (173035-11-5) → Hoveyda-Grubbs catalyst second generation (301224-40-8) + Hoveyda-Grubbs Catalyst II

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere; Glovebox;

DOI:10.1039/c7cy02278f

Reference yield: 95.0%

o-isopropoxystyrene (67191-35-9) + C56H64Cl2N4Ru + copper(l) chloride → Hoveyda-Grubbs catalyst second generation (301224-40-8) + (1-cyclooctyl-3-mesityl-2,3-dihydro-1H-imidazol-2-ylidene)copper(II) chloride

Guidance literature:

In dichloromethane; at 50 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c9cc05776e

Reference yield: 92.0%

Hoveyda-Grubbs catalyst first generation + N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate → Hoveyda-Grubbs catalyst second generation (301224-40-8)

Guidance literature:

With potassium 2-methylbutan-2-olate; In hexane; toluene; soln. of K compd. in toluene was added to suspn. of imidazolium salt in hexane under Ar; mixt. was stirred at room temp. for 1 h under Ar; solidRu complex was added; refluxed for 2 h under Ar; cooled to room temp.; solid CuCl added; refluxed for 2 h; evapd.; redisoolved in EtOAc; filtered through Celite; concd. (vac.); dissolved in CH2Cl2/MeOH (1/10, ambient temp.); concd. (vac.); filtered; washed (MeOH); dried (vac.);

DOI:10.1021/om0607651

upstream raw materials:

Hoveyda-Grubbs catalyst first generation

dichloro(tricyclohexylphosphino)(benzylidene)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)ruthenium(III)

o-isopropoxystyrene

Refernces

• 1、 Autenrieth, Benjamin,Willig, Felix,Pursley, Dominik,Naumann, Stefan,Buchmeiser, Michael R.. "Ionically tagged ru-alkylidenes for metathesis reactions under biphasic liquid-liquid conditions". . p. 3033 - 3040. Retrieved 2013.
• 2、 Pursley, Dominik,Plietker, Bernd. "Insertion of imines into vinylcyclopropanes catalyzed by nucleophilic iron complexes: A formal [3+2]-cycloaddition strategy for the synthesis of substituted pyrrolidine derivatives". . p. 2316 - 2318. Retrieved 2014.
• 3、 Vehlow, Kati,Maechling, Simon,K?hler, Katrin,Blechert, Siegfried. "Versatile Ru-based metathesis catalysts designed for both homogeneous and heterogeneous processes". . p. 5267 - 5277. Retrieved 2006.
• 4、 Liberman-Martin, Allegra L.,Grubbs, Robert H.. "Ruthenium Olefin Metathesis Catalysts Featuring a Labile Carbodicarbene Ligand". . p. 4091 - 4094. Retrieved 2017.
• 5、 Johns, Adam M.,Fiamengo, Bryan A.,Herron, Jessica R.,Bourg, Jean-Baptiste,Doppiu, Angelino,Karch, Ralf,Pederson, Richard L.. "Cis-Dichloro Sulfoxide Ligated Ruthenium Metathesis Precatalysts". supporting information. p. 218 - 222. Retrieved 2019/01/14.
• 6、 Kamal, Fadwa,Colombel-Rouen, Sophie,Dumas, Adrien,Guégan, Jean-Paul,Roisnel, Thierry,Dorcet, Vincent,Baslé, Olivier,Rouen, Mathieu,Mauduit, Marc. "Activation of olefin metathesis complexes containing unsymmetrical unsaturated N-heterocyclic carbenes by copper and gold transmetalation". supporting information. p. 11583 - 11586. Retrieved 2019/10/02.