GRUBBS CATALYST 2ND GENERATION

Base Information

• Chemical Name: GRUBBS CATALYST 2ND GENERATION
• CAS No.: 246047-72-3
• Molecular Formula: C46H65Cl2N2PRu
• Molecular Weight: 849.993
• European Community (EC) Number: 688-322-3
• Mol file: 246047-72-3.mol

Synonyms:(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylideneruthenium dichloride;(1,3-Dimesitylimidazolin-2-ylidene)(tricyclohexylphosphine)rutheniumdichloride;Benzylidene(1,3-dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)rutheniumdichloride;Benzylidenedichloro(1,3-dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)ruthenium;Grubbs Catalyst 2nd. generation;Grubbs II catalyst;Grubbs-Herrmann catalyst;Grubbs'Ru-dihydroimidazolylidene catalyst;Second generation Grubbs catalyst;[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium;

Chemical Property of GRUBBS CATALYST 2ND GENERATION

Chemical Property:

• Appearance/Colour: pink-brown to red-purple crystals or powder
• Melting Point: 143.5-148.5 °C(lit.)
• PSA: 20.07000
• LogP: 13.86190
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 848.330583
• Heavy Atom Count: 52
• Complexity: 927

Purity/Quality:

98% ^*data from raw suppliers

Grubbs Catalyst, 2nd Generation ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 36/37/38-11
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1)C)N2CCN(C2=[Ru](=CC3=CC=CC=C3)(Cl)Cl)C4=C(C=C(C=C4C)C)C)C.C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
• 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.
• Uses: suzuki reaction Grubbs Catalyst? M204 can be used as a catalyst for ring-closing metathesis (RCM), cross-metathesis, and ring-opening metathesis polymerization (ROMP). It is also used to synthesize trisubstituted olefins with excellent functional group tolerance and selectivity via cross-metathesis and ring closing metathesis reactions.It can also be used as a catalyst:To synthesize coumarins from phenolic compounds via RCM.To cleave secondary (E)-allyl vic-diols to aldehydes.

Technology Process of GRUBBS CATALYST 2ND GENERATION

There total 23 articles about GRUBBS CATALYST 2ND GENERATION 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: 94.0%

Grubbs catalyst first generation + 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene (173035-11-5) → tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride (246047-72-3)

Guidance literature:

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

DOI:10.1039/c7cy02278f

Reference yield: 91.0%

1,3-di(2,4,6-trimethylphenyl)-2-(pentafluorophenyl)-2,4,5-trihydroimidazole (782479-45-2) + Grubbs catalyst first generation → tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride (246047-72-3)

Guidance literature:

In toluene; mixt. of Ru complex and imidazolidine in toluene was heated at 60°C for 4 h;

DOI:10.1021/om060949f

Reference yield: 87.0%

Grubbs catalyst first generation + 1,3-bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine (260054-47-5) → tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride (246047-72-3)

Guidance literature:

In toluene; mixt. of Ru complex and imidazolidine in toluene was heated at 60°C for 4 h;

DOI:10.1021/om060949f

upstream raw materials:

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

tricyclohexylphosphine

Downstream raw materials:

(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)Cl₂Ru=CH-o-OiPrC₆H₄

carbonylchlorohydridobis(tricyclohexylphosphine)ruthenium(II)

Grubbs catalyst third generation

[1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium

Refernces

• 1、 Blum, Angela P.,Ritter, Tobias,Grubbs, Robert H.. "Synthesis of N-heterocylic carbene-containing metal complexes from 2-(pentafluorophenyl)imidazolidines". . p. 2122 - 2124. Retrieved 2007.
• 2、 Sanford, Melanie S.,Love, Jennifer A.,Grubbs, Robert H.. "A versatile precursor for the synthesis of new ruthenium olefin metathesis catalysts". . p. 5314 - 5318. Retrieved 2001.
• 3、 -. "SYNTHESIS AND CHARACTERIZATION OF METATHESIS CATALYSTS". Paragraph 000150; 000151. . Retrieved 2018/03/25.