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Preparation method of palladium catalyzed 1,2-trans diaryl alkene

A diarylolefin, palladium catalyzed technology, applied in the preparation of organic compounds, halogenated hydrocarbons, carbon-based compounds and other directions, can solve problems such as high temperature, achieve simple operation, high yield and selectivity, low good adaptability

Inactive Publication Date: 2019-05-28
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the decarboxylation reaction still faces great challenges. For example, most of the reported decarboxylation methods require high temperature and excessive metals to promote the decarboxylation reaction; The application of the decarboxylation reaction has been rarely reported so far, which also points out the direction for the future development of the decarboxylation reaction

Method used

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  • Preparation method of palladium catalyzed 1,2-trans diaryl alkene
  • Preparation method of palladium catalyzed 1,2-trans diaryl alkene
  • Preparation method of palladium catalyzed 1,2-trans diaryl alkene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In a reaction flask, add phenylacrylic acid (1.0mmol), phenyl p-toluenesulfonate (1.1mmol), catalyst (0.05mmol), cocatalyst (0.2mmol), base (2.0mmol) and 2mL solvent, stir, then heat Reaction was carried out at 100°C. After 12 hours of reaction, TLC monitored the reaction to be complete, cooled to room temperature, filtered off the solid, added 3 mL of water and extracted three times with ethyl acetate (3 mL each time), combined the extracts, and dried over anhydrous sodium sulfate. After spin-drying the solvent, use the mixed solvent of petroleum ether and ethyl acetate as the eluent for column separation to obtain the product. The reaction formula, reaction conditions and reaction results are shown in Table 1.

[0033] Table 1 Reaction conditions and reaction results of Example 1

[0034]

[0035]

[0036]

[0037] a Reaction conditions: phenylacrylic acid (1.0mmol), p-toluenesulfonate (1.1mmol), catalyst (5mol%), cocatalyst (20mol%), base (2.0mmol), solven...

Embodiment 2

[0040] In the reaction flask, add aryl acrylic acid (1.0mmol), phenyl p-toluenesulfonate (1.1mmol), PdCl 2 (dppf)(0.05mmol), CuCl 2 (0.2mmol), KOAc (2.0mmol) and 2mL solvent DMI (1,3-dimethyl-2-imidazolinone), stirred, then heated to 100 ° C for reaction, after 12 hours of reaction, TLC monitoring reaction was complete, Cool down to room temperature, filter out the solid, add 3 mL of water and extract three times with ethyl acetate (3 mL each time), combine the extracts, dry over anhydrous sodium sulfate, spin to dry the solvent, and use a mixed solvent of petroleum ether and ethyl acetate as The eluent is subjected to column separation to obtain the product. Reaction formula and reaction result (yield is separation yield) are as follows:

[0041]

[0042]

Embodiment 3

[0044] In the reaction flask, add p-methoxyphenyl acrylic acid (1.0mmol), aryl p-toluenesulfonate (1.1mmol), PdCl 2 (dppf)(0.05mmol), CuCl 2 (0.2mmol), KOAc (2.0mmol) and 2mL solvent DMI (1,3-dimethyl-2-imidazolinone), stirred, then heated to 100 ° C for reaction, after 12 hours of reaction, TLC monitoring reaction was complete, Cool down to room temperature, filter out the solid, add 3 mL of water and extract three times with ethyl acetate (3 mL each time), combine the extracts, dry over anhydrous sodium sulfate, spin to dry the solvent, and use a mixed solvent of petroleum ether and ethyl acetate as The eluent is subjected to column separation to obtain the product. Reaction formula and reaction result (yield is separation yield) are as follows:

[0045]

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Abstract

The invention discloses a preparation method of palladium catalyzed 1,2-trans diaryl alkene. The method comprises the following steps that under the effects of catalysts, cocatalysts and alkali, arylacrylic acid and aromatic esters p-toluene sulfonate take decarboxylation coupling reaction in an organic solvent; after the reaction is finished, the 1,2-trans diaryl alkene is obtained through posttreatment. The method has the advantages that through C-O bond fracture, the operation is simple; a stable palladium catalyst with low cost is used; the substrate applicability is high; the harsh reaction conditions and the addition of strong alkali are not needed; the trans 1,2-diaryl alkene can be generated at high selectivity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a palladium-catalyzed preparation method of 1,2-trans diaryl olefins. Background technique [0002] The transition metal-promoted coupling reaction has the advantages of simplicity and high efficiency, so it is widely used in the synthesis of various compounds. However, the metal-organic reagents used in the reaction need to be prepared or activated in advance. Significant amounts of metal by-products are also produced. Moreover, most of these reagents are highly toxic, difficult to store and handle, and expensive, and do not meet the purpose of green chemistry pursued by scientists today. Therefore, finding and developing more stable, cheap and harmless new reagents has triggered a new research boom. Carboxylic acid compounds have attracted the attention of scientists due to their wide range of sources, low price, and easy storage and handling. The decarboxylation ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/32C07C15/52C07C41/30C07C43/215C07C15/50C07C201/12C07C205/06C07C17/263C07C22/08C07C253/30C07C255/50C07C255/33C07C45/68C07C49/796C07C25/24C07D213/16C07D277/22C07D277/24
Inventor 赵保丽
Owner SHAOXING UNIVERSITY
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