Method for preparing substituted alkene

A technology for olefins and halogenated hydrocarbons is applied in the field of catalytic coupling synthesis of substituted olefins to achieve the effects of easy availability of raw materials, simple operation and convenient post-processing

Inactive Publication Date: 2012-10-24
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for the traditional Heck reaction, cinnamate derivatives are generally obtained, which has

Method used

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  • Method for preparing substituted alkene
  • Method for preparing substituted alkene
  • Method for preparing substituted alkene

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0031] Example one:

[0032] Load Pd(dppf) sequentially into a Schlenk test tube 2 Cl 2 (0.015 mmol), triethylamine (1.0 mmol), potassium vinyl fluoroborate (0.5 mmol) and DMF (2 mL), add iodobenzene (0.5 mmol) with a micro injector. Then the system was sealed and heated in an oil bath at 120°C for about 12 hours, and p-methoxy iodobenzene (0.5 mmol) was added, and then the system was sealed and heated in an oil bath at 120°C for about 24 hours. Then let the system cool to room temperature, add 2 mL of water to quench the reaction, then extract with ethyl acetate (4 mL×3), combine the organic phases and dry with anhydrous sodium sulfate, concentrate and pass through simple column chromatography (using eluent Petroleum ether: ethyl acetate = 24:1), the coupling product 1-phenyl-2-p-methoxyphenylethylene (85.2 mg) can be obtained, and the yield is 81%. Its nuclear magnetic data is: 1 H NMR (400 MHz, CDCl 3 ) (δ, ppm) 3.81 (s, 3H), 6.89 (d, J = 8.4 Hz, 2H), 6.96 (d, J = 16.0 Hz, 1...

Example Embodiment

[0033] Example two

[0034] Load Pd(dppf) sequentially into a Schlenk test tube 2 Cl 2 (0.015 mmol), triethylamine (1.0 mmol), potassium vinyl fluoroborate (0.5 mmol) and DMF (2 mL), add p-chloroiodobenzene (0.5 mmol) with a microinjector. Then the system was sealed and heated in an oil bath at 120°C for about 12 hours, and p-fluoroiodobenzene (0.5 mmol) was added, and then the system was sealed and heated in an oil bath at 120°C for about 24 hours. Then let the system cool to room temperature, add 2 mL of water to quench the reaction, then extract with ethyl acetate (4 mL×3), combine the organic phases and dry with anhydrous sodium sulfate, concentrate and pass through simple column chromatography (using eluent Petroleum ether: ethyl acetate = 24:1) to obtain the coupling product 1-p-chlorophenyl 2-p-fluorophenylethylene (97.4 mg), the yield was 84%. Its nuclear magnetic data is: 1 H NMR (400 MHz CDCl 3 ) 6.98 (d, J = 16.4, 1H), 7.04-7.09 (m, 3H), 7.35 (d, J = 8.8, 2H), 7.44 (...

Example Embodiment

[0035] Example three

[0036] Load Pd(dppf) in a Schlenk test tube sequentially 2 Cl 2 (0.015 mmol), triethylamine (1.0 mmol), potassium vinyl fluoroborate (0.5 mmol) and DMF (2 mL), add p-fluoroiodobenzene (0.5 mmol) with a micro injector. Then the system was sealed and heated in an oil bath at 120°C for about 12 hours, and p-methoxy iodobenzene (0.5 mmol) was added, and then the system was sealed and heated in an oil bath at 120°C for about 24 hours. Then let the system cool to room temperature, add 2 mL of water to quench the reaction, then extract with ethyl acetate (4 mL×3), combine the organic phases and dry with anhydrous sodium sulfate, concentrate and pass through simple column chromatography (using eluent Petroleum ether: ethyl acetate = 24:1) to obtain the coupling product 1-p-methoxyphenyl 2-p-fluorophenylethylene (92.4 mg), the yield was 81%. Its nuclear magnetic data is: 1 H NMR (400 MHz CDCl 3 ) 3.84 (s, 3H), 6.84-6.96 (m, 4H), 7.03 (t, J = 8.8, 2H), 7.41-7.47 (m...

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Abstract

The invention discloses a method for preparing substituted alkene. The method is characterized in that Suzuki coupling reaction and Heck coupling reaction occur in turn under the action of a catalyst with a vinyl fluoride potassium silicate compound and halogenated hydrocarbon as a reaction substrate to obtain the substituted alkene, wherein the halogenated hydrocarbon is a halogenated aromatic hydrocarbon or a halogenated aliphatic hydrocarbon, the halogen atom is selected from chlorine, bromine or iodine; the vinyl fluoride potassium silicate compound refers to an olefin compound with double bond connected with boric acid group, the catalyst is a palladium catalyst. The method provided by the invention has the advantages of simple operation, mild condition, convenient post-processing, easiness of geting raw materials and wide range of suitable substrates.

Description

technical field [0001] The invention relates to the preparation of a substituted olefin, in particular to a method for catalytically coupling and synthesizing a substituted olefin, in particular to a method for preparing a substituted olefin through a series reaction of Suzuki coupling and Heck coupling. Background technique [0002] Substituted alkene structural units widely exist in the intermediates of medicine and materials, and their effective synthesis methods have attracted widespread attention in the past decade. Therefore, it is particularly important to find a new synthetic method for its development in application. Among them, the Heck reaction is one of the effective methods for the synthesis of compounds such as aromatic substituted alkenes or allenes. However, for the traditional Heck reaction, cinnamate derivatives are generally obtained, which has certain limitations for the synthesis of substituted olefin compounds with other functional groups. [0003] In...

Claims

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Application Information

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IPC IPC(8): C07C43/215C07C43/225C07C41/30C07C25/28C07C17/263C07C15/52C07C1/32C07B37/04
Inventor 毛金成屈孝铭李廷义
Owner SUZHOU UNIV
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