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Method for synthesizing second generation Grubbs catalyst

A synthesis method and catalyst technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., to achieve good overall yield, simple, safe and easy-to-control operation process Effect

Inactive Publication Date: 2010-07-14
XIAMEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the second generation Grubbs catalyst (H 2 IMes) (PCy 3 )(Cl) 2 Ru=CHPh has such an important application in the field of organic synthetic chemistry, but its synthetic method is limited to a kind of method at present, promptly by the ligand substitution reaction to the first generation Grubbs catalyst synthesis second generation Grubbs catalyst (Scholl, M.; Ding, S.; Lee, C.W; Grubbs, R.H. Org. Lett. 1999, 1, 953)

Method used

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  • Method for synthesizing second generation Grubbs catalyst
  • Method for synthesizing second generation Grubbs catalyst

Examples

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Embodiment 1

[0020] Step 1 Synthesis of compound H 2 IMes 2

[0021] Add H to the reaction flask 2 Imes(H)(Cl)(0.40g, 1.16mmol), THF(10mL), dissolved and added KNSi(CH 3 ) 3 (0.53mL, 1.16mmol), stirred at room temperature for 0.5h, filtered to remove the residue, and the filtrate was dried, and after vacuum drying, compound H 2 IMes, 83% yield.

[0022] Step 2 synthesizes the second generation Grubbs catalyst (H 2 IMes) (PCy 3 )(Cl) 2 Ru=CHPh3

[0023] Add compound H to the reaction vial 2 IMes 2 (181mg, 0.59mmol), Ru(p-cymene) (COD) (200mg, 0.59mmol), PCy 3 (165mg, 0.59mmol) and toluene (10mL), dissolved and added PhCHCl 2 (0.10mL, 0.79mmol), stirred and reacted at room temperature for 30h, concentrated the solution under reduced pressure to about 1mL, added 10mL of methanol, precipitated a purple-brown solid, filtered it with a sand core, washed the solid with 3×3mL methanol, and dried in vacuo to obtain the compound (H 2 IMes) (PCy 3 )(Cl) 2 Ru=CHPh3, yield 50%. figure 1 ...

Embodiment 2

[0025] Step 1 Synthesis of compound H 2 IMes 2

[0026] Compound H 2 The operation of IMes 2 is identical with the operation in embodiment 1, reactant H 2 IMes(H)(Cl) changed to H 2 Imes(H)(BF 4 ), yield 84%.

[0027] Step 2 synthesizes the second generation Grubbs catalyst (H 2 IMes) (PCy 3 )(Cl) 2 Ru=CHPh3

[0028] Compound (H 2 IMes) (PCy 3 )(Cl) 2 The synthesis steps of Ru=CHPh 3 are the same as in Example 1.

Embodiment 3

[0030] Step 1 Synthesis of compound H 2 IMes 2

[0031] Compound H 2 The operation of IMes 2 was the same as that in Example 1, the solvent was changed to hexane, stirred at room temperature for 2 h, and the yield was 85%.

[0032] Step 2 synthesizes the second generation Grubbs catalyst (H 2 IMes) (PCy 3 )(Cl) 2 Ru=CHPh3

[0033] Compound (H 2 IMes) (PCy 3 )(Cl) 2 The synthesis steps of Ru=CHPh 3 are the same as in Example 1.

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Abstract

The invention discloses a method for synthesizing a second generation Grubbs catalyst, which relates to a catalyst, in particular to a metal carbine compound (H2IMes)(PCy3)(Cl)2Ru=CHPh(H2IMes is 1,3-di-(2,4,6-trimethylphenyl)imidazole alkyl, and PCy3 is tricyclohexyl phosphine) with favorable olefin double-decomposition catalytic activity, namely the second generation Grubbs catalyst. The method comprises the following step of reacting a zero valence ruthenium compound Ru(p-cymene)(COD)(p-cymene is paracymene, and COD is 1,5-cyclooctadiene) with PCy3, PhCHCL2 and a nitrogen heterocyclic carbine compound in toluene or other hydrocarbon solvents to obtain the second generation Grubbs catalyst. The invention has low cost and easy acquisition of used raw materials, simple and safe operation process, easy control and high yield and is particularly suitable for industrialized large production.

Description

technical field [0001] The present invention relates to a kind of catalyzer, relate to a kind of metal carbene compound (H 2 IMes) (PCy 3 )(Cl) 2 Ru=CHPh(H 2 IMes is 1,3-bis-(2,4,6-trimethylphenyl) imidazolidine; PCy 3 is tricyclohexylphosphine), the synthetic method of the second generation Grubbs catalyst (Ma Yuguo, University Chemistry, 2006, 21, 1). Background technique [0002] Olefin metathesis is one of the most important and useful types of reactions in organic chemistry. This reaction enables the coupling of normally chemically inert double bonds to each other, which greatly expands people's imagination space when constructing compound skeletons. At the same time, because the reaction has the characteristics of mild reaction conditions and high yield, and most of the organic groups do not need to be protected in this reaction, it has received extensive attention from academia and industry in recent years. [0003] Metallocarbenes, a class of metal-carbon double...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F19/00C07F15/00B01J31/12C07C6/04
Inventor 温庭斌林毅
Owner XIAMEN UNIV
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