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Method for synthesizing polysubstituted olefins

A multi-substituted, olefin technology, applied in the preparation of halogenated hydrocarbons, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of high cost, pollute the environment, difficult to apply to large-scale production, etc., to improve activity and durability, The effect of low catalyst dosage and recyclable catalyst

Inactive Publication Date: 2015-02-11
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The purpose of the present invention is to provide a method for synthesizing multi-substituted olefins, to solve the problems of high cost and environmental pollution in the traditional homogeneous metal catalyst catalyzed Heck reaction existing in the prior art, and the problem that it is difficult to apply to large-scale production

Method used

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  • Method for synthesizing polysubstituted olefins
  • Method for synthesizing polysubstituted olefins
  • Method for synthesizing polysubstituted olefins

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1. Catalyst Preparation

[0023] (1) Weigh 465.9 mg (5 mmol) of aniline and dissolve it in 50 ml of 1M hydrochloric acid aqueous solution to obtain solution 1;

[0024] (2) Weigh 22 mg (0.125 mmol) of palladium chloride and dissolve it in 50 ml of 1M hydrochloric acid aqueous solution to obtain solution 2;

[0025] (3) Solution 1 and Solution 2 were mixed, stirred for 2 minutes, and then left to stand for 24 hours. Then adjust the pH to 7.0 with 1M aqueous sodium hydroxide solution to produce a flocculent precipitate;

[0026] (4) Centrifuge and wash the precipitate with deionized water. Then add 6 ml of deionized water and shake the suspension. The suspension can be stored in the refrigerator (4 degrees) for a long time;

[0027] (5) Take 0.6 ml of the above suspension and dilute to 5 ml with deionized. 0.5 ml of it was centrifuged to remove water, and the precipitate was used to catalyze the Suzuki coupling reaction (1 mmol reaction scale). IPC analysis proves t...

Embodiment 2

[0031] Other conditions are the same as in Example 1, and the reaction using different bases is checked, and the experimental results are shown in Table 1.

[0032] The inspection of different alkali effects in table 1

[0033]

[0034]

[0035] From the above results, it can be seen that the effect of using most organic or inorganic bases is very poor, but the effect of using tertiary amines is good. And the effect of using ethyl diisopropylamine will far surpass other tertiary amines (embodiment 1).

Embodiment 3

[0037] Other conditions are the same as in Example 1, and the reactions under different ethyldiisopropylamine dosages are checked, and the experimental results are shown in Table 2.

[0038] The inspection of different ethyldiisopropylamine consumption of table 2

[0039]

[0040]

[0041] From the above results, it can be known that the dosage of ethyldiisopropylamine is preferably 100 mol% (based on reactants) (Example 1).

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Abstract

The invention discloses a method for synthesizing polysubstituted olefins. The method comprises the following step: by using polyaniline-supported nano palladium as a catalyst and ethyl diisopropyl amine as alkali, catalyzing Heck reaction between olefin C-H and halohydrocarbons to prepare the polysubstituted olefins. Compared with the traditional Heck reaction, the method disclosed by the invention has the advantages of high yield, mild reaction conditions, no use of phosphine ligand, low catalyst consumption, recoverable catalyst and the like, and is suitable for pharmaceutical industry.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing multi-substituted olefins. . Background technique [0002] Multi-substituted alkenes are important organic compounds and are widely used in material chemistry, organic synthesis, medicinal chemistry and chemical industry. The Heck reaction, which synthesizes multi-substituted alkenes through metal-catalyzed coupling of alkenes C-H and halogenated hydrocarbons, is widely used in organic synthesis due to its ability to accurately synthesize target compounds. The discoverer of this reaction was also awarded the Nobel Prize in Chemistry in 2011. [0003] However, traditional homogeneous metal catalysts catalyze the Heck reaction, 1，2 It has various disadvantages such as difficult recovery of the catalyst and the need to add toxic phosphine ligands, which makes the reaction cost high and pollutes the environment, making it difficult to apply to large-scale...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/00C07C15/52C07C2/86C07C43/215C07C41/30C07C39/21C07C37/18C07C25/24C07C17/266C07C15/58C07D213/127C07D213/16C07D303/08C07C17/269C07C69/618C07C67/343C07C255/34C07C253/30C07C22/08C07C205/06C07C201/12
CPCY02P20/584
Inventor 俞磊黄亚萍刘铭轩杨成根丁克鸿徐清
Owner YANGZHOU UNIV
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