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Synthesis method of carbonate modified fluoride-free organic phosphine ligand

A synthesis method and organic phosphine technology are applied in the synthesis field of carbonate-modified fluorine-free organic phosphine ligands, which can solve environmental problems, high price of fluorocarbon fluorine-containing ligands, etc. The effect of using

Inactive Publication Date: 2017-03-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the fatal flaw of phosphine ligands modified with fluoroalkyl groups is that fluorocarbons and corresponding fluorine-containing ligands are very expensive, and the large-scale use of fluorine-containing compounds will cause serious environmental problems

Method used

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  • Synthesis method of carbonate modified fluoride-free organic phosphine ligand
  • Synthesis method of carbonate modified fluoride-free organic phosphine ligand
  • Synthesis method of carbonate modified fluoride-free organic phosphine ligand

Examples

Experimental program
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Effect test

Embodiment 1

[0026] The first step, the synthesis of compound 2a (two (4-methoxyphenyl) phenylphosphine)

[0027] The magnesium powder was washed with hydrochloric acid and acetone respectively, and sucked dry. THF was refluxed with metal Na until the benzophenone turned dark purple. Add fresh Mg powder into the reaction device, N 2 Replaced 3 times, followed by adding I 2 pellets and refined THF. N 2 Under protection, the dried compound 1a (4-bromoanisole) was transferred to the dropping funnel. The reaction was initiated by heating, and a THF solution of 4-bromoanisole was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 1 h to obtain a dark black mixture. Phenyl phosphorus dichloride was slowly added dropwise to the Grignard reagent, and after the addition was complete, stirred for 2h. The reaction mixture was slowly added to 10% glacial hydrochloric acid aqueous solution, extracted with ether, and the solvent was d...

Embodiment 2

[0041] The first step, the synthesis of compound 2b ((4-methoxyphenyl) diphenylphosphine)

[0042] The magnesium powder was washed with hydrochloric acid and acetone respectively, and sucked dry. THF was refluxed with metal Na until the benzophenone turned dark purple. Add the newly prepared Mg powder into the dropwise reflux reaction device, and then use N 2 Replaced 3 times, followed by adding I 2 pellets and refined THF, in N 2 Under protection, the dried compound 1a (4-bromoanisole) was transferred to the dropping funnel. The reaction was initiated by heating, and a THF solution of 4-bromoanisole was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 1 h to obtain a dark black mixture. Slowly add diphenylphosphorus chloride dropwise to the Grignard reagent, after the addition is complete, stir for 2h. The reaction mixture was slowly added to 10% aqueous glacial hydrochloric acid, extracted with dichlorome...

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Abstract

The invention relates to the field of organic synthesis and provides a synthesis method of a carbonate modified fluoride-free organic phosphine ligand. The synthesis method comprises the following steps: preparing a Grignard reagent from the raw material p-bromoanisole or derivative thereof; enabling the Grignard reagent to react with a phosphorus source to generate a skeleton structure molecule with triphenylphosphine; and performing oxidation, demethylation, nucleophilic substitution and reduction to obtain a target molecular structure. The synthesis method has the following effects and benefits: a novel carbon dioxide-philic organic phosphine ligand is synthesized, the solubility of the phosphine ligand in supercritical CO2 is increased, and application of a fluoride-free phosphine ligand organic metal catalyst in supercritical CO2 is realized. Moreover, the organic carbonate compound is insoluble in a weakly (non-) polar organic solvent (such as alkane compounds), the property enables a phase splitting function of the carbonate modified fluoride-free organic phosphine ligand in the reaction system, and the recycling and reusing of the catalyst are realized.

Description

technical field [0001] The invention relates to the field of chemical organic synthesis and provides a method for synthesizing a carbonate-modified fluorine-free organic phosphine ligand. Background technique [0002] Phosphine ligands in supercritical CO 2 The poor solubility in medium limits the performance of its corresponding organometallic catalysts in supercritical CO 2 Catalytic application in the medium, so we modified it. The most successful so far is the introduction of fluorine-containing groups. However, the fatal defect of phosphine ligands modified with fluoroalkyl groups is that fluorocarbons and corresponding fluorine-containing ligands are very expensive, and the large-scale use of fluorine-containing compounds will cause serious environmental problems. Therefore, the design and synthesis of new pro-CO 2 Phosphine ligands become supercritical CO 2 It is one of the research focuses of transition metal coordination catalysis in media. [0003] in pro co ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655
CPCC07F9/65515Y02P20/54
Inventor 姜文凤袁宵张天保范玲霞王慧龙
Owner DALIAN UNIV OF TECH
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