CN118166369A - Electrochemical synthesis method of E-type styrene derivative - Google Patents

Electrochemical synthesis method of E-type styrene derivative Download PDF

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Publication number
CN118166369A
CN118166369A CN202410408334.6A CN202410408334A CN118166369A CN 118166369 A CN118166369 A CN 118166369A CN 202410408334 A CN202410408334 A CN 202410408334A CN 118166369 A CN118166369 A CN 118166369A
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type styrene
electrochemical
electrochemical synthesis
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styrene derivatives
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吴海虹
董梦柯
贾帅强
董开武
韩布兴
何鸣元
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East China Normal University
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    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/05—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/07—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/09—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/11—Halogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides an electrochemical synthesis method of an E-type styrene derivative. The invention uses the free radical chain reaction initiated by electrochemistry to isomerise the aromatic compound with allyl structure into E-type styrene derivative. Comprising the following steps: in an electrochemical reaction tank, an aromatic compound with an allyl structure is taken as a substrate, and a solvent and an electrolyte are added; the substrate generates free radical active species under the activation of the electrode, and chain isomerism is initiated, so that the E-type styrene derivative is obtained. The method does not need a metal catalyst and a ligand, has mild conditions, is green and safe, is easy to enlarge the scale, has high product yield, is easy to separate and purify, and is suitable for industrialized green production.

Description

Electrochemical synthesis method of E-type styrene derivative
Technical Field
The invention belongs to the field of organic synthesis, and relates to an electrochemical synthesis method of an E-type styrene derivative.
Background
Styrene derivatives are widely found in various natural products, drug molecules and fragrances, such as the natural products (-) -Polysphorin and Fumimycin, rosuvastatin calcium, which are useful as hypolipidemic agents, and anethole as a food additive. The method for producing styrene derivatives by isomerization has been developed in a large amount, and among them, a method for producing styrene derivatives by isomerization using an allylic aromatic compound as a raw material is favored. Because of the wide source of allylic aromatics, the manner of isomerization is also very diverse. Current isomerisation processes can be broadly divided into base catalysis and metal catalysis. However, the alkali catalysis requires high temperature, has high energy consumption, and has high alkali consumption and difficult control of the configuration of the product. While metal catalysis can well adjust the selectivity of the configuration, noble metals or complexes of non-noble metals and ligands are generally required as catalysts, and are difficult to recycle. And the reaction conditions are generally harsh, the production cost is high, and the industrial production is not facilitated. As in 2022, phil s.baran reported cobalt-catalyzed double bond isomerization. Patent CN 110878012A also reports an isomerization in the presence of metallic nickel salts, bipyridine ligands and additives. Both processes require complex ligand-constituted catalytic systems to perform successfully.
In view of the above, there is an urgent need to develop a method for synthesizing styrene derivatives with low reaction condition requirements, convenient operation, good production safety, good environmental friendliness, low cost and high product yield.
Disclosure of Invention
In view of the above problems associated with the prior art synthesis of styrene derivatives, the present invention provides a novel concept for synthesizing E-type styrene derivatives, which isomerises aromatic compounds having an allyl structure into E-type styrene derivatives using an electrochemically initiated free radical chain reaction. Specifically, the invention comprises the following technical scheme:
An electrochemical synthesis method of E-type styrene derivatives is characterized in that an aromatic compound with an allyl structure is isomerised into E-type styrene derivatives as shown in a formula II.
An electrochemical synthesis method of an E-type styrene derivative is characterized by comprising the following steps:
In an electrochemical reaction tank, adding an electrolyte solution, taking an aromatic compound with an allyl structure shown in a formula I as a substrate in normal pressure atmosphere, keeping the temperature of the solution constant, carrying out electrolysis in a constant current mode or a constant voltage mode, and generating free radical active species by the substrate under the activation of an electrode to initiate chain isomerism so as to obtain the E-type styrene derivative II.
Wherein, the substrate I is an aromatic compound with an allyl structure, the aromatic structure comprises a benzene ring structure, and other aromatic groups such as furyl, thienyl, pyridyl, naphthyl and the like are also included; the aromatic structure may have an electron withdrawing group such as an ester group, an amide group, an acyl group, or a halogen; or electron donating groups such as methoxy and amino; r 1,R2,R3 can be alkyl or ester, amide, acyl with chain length between C 1～C10.
The electrochemical reaction tank is a single tank or a double tank, and when the electrochemical reaction tank is a double tank, the cathode tank and the anode tank are separated by a cation exchange membrane or a glass sand core, preferably a single tank.
Among them, the electrode is selected from metal sheets such as iron, copper, nickel, cobalt, zinc, aluminum, magnesium, lead, silver, platinum, or any one of glassy carbon, stainless steel, and graphite, and is preferably an iron electrode.
Wherein the electrolyte solution is selected from an organic solvent/electrolyte or water/electrolyte, wherein the organic solvent is selected from acetonitrile, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, tetrahydrofuran, dichloromethane, ethylene glycol dimethyl ether or a mixture of two or more thereof; the electrolyte is selected from tetraalkylammonium salts such as tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium perchlorate, tetrabutylammonium hexafluorophosphate, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium iodide, tetraethylammonium perchlorate, tetramethylammonium tetrafluoroborate or inorganic salts such as sodium iodide, potassium sulfate, sodium chloride, sodium triflate, etc., preferably acetonitrile solution of sodium iodide.
The reaction temperature in the step is between-30 and 200 ℃, preferably 20 to 40 ℃.
The reaction atmosphere in the step is air atmosphere or inert gas atmosphere, and the inert gas is selected from nitrogen, argon, preferably argon.
The current density in the step is between 0.01 and 1000mA cm -2, the working voltage is between 0.1 and 220V, preferably 50 to 100mA cm -2, and 20 to 30V.
The substrate concentration in the step is between 0.01 and 7mol L -1, preferably between 0.5 and 1mol L -1.
The concentration of the electrolyte solution in the step is between 0.001 and 1mol L -1, preferably between 0.5 and 1mol L -1.
The electrochemical synthesis method of the E-type styrene derivative provided by the invention has the following beneficial effects:
(1) Aromatic compounds with allyl structures are used as substrates, free radical active species are generated under electrode activation, chain isomerization is initiated, and thus the E-type styrene derivative II is obtained. The process is simple, the reaction condition is mild, and the operability is strong.
(2) In the preparation of the E-type styrene derivative II, an electric initiation free radical chain isomerization synthesis strategy is adopted, so that the use of a large number of metal catalysts and complex ligands is avoided, and meanwhile, the configuration of a product can be well controlled. The solvent and the electrode used in the preparation method can be recycled, hazardous reagents are not used, harmful substances are not generated, and the preparation method is environment-friendly.
(3) In the preparation of the E-type styrene derivative II, the concentration of a substrate is high, the reaction is fast, the post-treatment is simple and convenient, the yield is high and can reach 99%, the Z/E is high to 1/99, and the product purity is high and the amplification is easy.
The invention uses the free radical chain reaction initiated by electrochemistry to isomerise the aromatic compound with allyl structure into E-type styrene derivative. The reaction raw materials are easy to obtain, the conditions are mild, and the Faraday efficiency is high. The invention can carry out rapid isomerism under the conditions of room temperature and high concentration, is favorable for carrying out amplification reaction, and has the advantages of easy separation of products, high purity of the obtained products and high configuration selectivity. Therefore, the method is a reasonable optimization scheme from the perspective of production safety and the economical perspective of reducing production cost, and has popularization and application prospects.
Drawings
FIG. 1 is a gas chromatogram of (E) - β -methylstyrene in example 1;
FIG. 2 is a graph showing the hydrogen spectrum of (E) -beta-methylstyrene in example 1.
Detailed Description
In order to develop a preparation method of the E-type styrene derivative with low reaction condition requirements, convenient operation, good production safety, environmental protection, low cost and high product yield, the invention takes an aromatic compound with an allyl structure as a substrate, and generates free radical active species under the activation of an electrode to trigger chain isomerization, so as to obtain the E-type styrene derivative II:
the term "compound of formula X" is sometimes expressed herein as "formula X" or "compound X", as will be appreciated by those skilled in the art. For example, both compounds of formula I and compound I refer to the same compound.
In a preferred embodiment, after completion of the reaction in each of the above steps, post-treatment operations such as filtration, washing, decolorization purification, crystallization, drying and the like may be performed according to common general knowledge in the art. On the basis of conforming to the common knowledge in the field, the above preferred conditions can be arbitrarily combined to obtain the preferred examples of the invention.
The examples relate to the amounts, amounts and concentrations of various substances, wherein the percentages refer to percentages by mass unless otherwise specified.
In the examples herein, if no specific explanation is made for the reaction temperature or the operating temperature, the temperature is generally referred to as room temperature (15 to 30 ℃).
The raw materials used in the embodiment of the invention are as follows: allylbenzene, p-methoxyallylbenzene, p-bromoallylbenzene, 1, 4-dihydroxynaphthalene; tetrabutylammonium iodide, ammonium chloride, sodium iodide, potassium sulfate; nickel electrode, iron electrode, platinum electrode, graphite electrode, tetrahydrofuran, N-dimethylformamide, acetonitrile, dichloromethane, water, nitrogen gas with a purity of 99.99% and argon gas with a purity of 99.99%. The organic solvents and the like are all analytically pure and are directly used. Reagents were purchased from Shanghai chemical reagent company, china medicine (group).
The equipment used is: constant-current electrolyzer, electrochemical reaction tank and magnetic stirrer.
Detection instrument: nuclear magnetic resonance apparatus: using Bruker superconducting nuclear magnetic resonance spectrometer; the resonance frequency is 500MHz; CDCl 3 was used as solvent and TMS was used as internal standard. Gas chromatography: model 7890A, the column used was an HP-5 gas column.
Example 1
In a single-tank reaction tank, filling nitrogen gas into a reaction tank with the volume of 150mL, and adding 3.69g (10 mmol) of tetrabutylammonium iodide, 1.18g (10 mmol) of allylbenzene and 100mL of tetrahydrofuran; stirring and continuously introducing nitrogen gas after the mixture is dissolved; taking nickel sheets with the surface area of 10cm 2 as a cathode and an anode, introducing 20mA current, and continuously electrolyzing for 3 hours at the temperature of 20 ℃; after the reaction, the solvent was removed under vacuum, 100mL of water was added, extraction was performed three times with 100mL of ethyl acetate, the organic phases were combined, the solvent was removed under vacuum, and the mixture was purified by distillation to obtain (E) -beta-methylstyrene.
The mass of the isomerism product (E) -beta methyl styrene is 1.21g, the yield is 95%, and the Z/E is 1/99; the (E) -beta-methylstyrene was subjected to a gas phase test, as shown in FIG. 1, with a retention time of 9.27min; nuclear magnetic resonance detection is carried out on the (E) -beta-methylstyrene, and a hydrogen spectrum diagram of the (E) -beta-methylstyrene is shown in figure 2. As can be seen from fig. 2:
1H-NMR(CDCl3,500Hz)δppm：1.90-1.92(d,3H),6.23-6.30(m,1H),6.42-6.45(d,1H),7.20-7.23(t,1H),7.30-7.37(m,4H).
δ=1.90-1.92 ppm: hydrogen in CH 3 is unimodal and the number is 3;6.23-6.30ppm: the hydrogen on the alkenyl carbon adjacent to the methyl group is multiple front, and the number is 1;6.42-6.45ppm: is hydrogen on benzylic carbon, and the number of double peaks is 1;7.20-7.37ppm: the number of hydrogen on the benzene ring is 5.
Example 2
In a single-tank reaction tank, argon gas is filled in a reaction tank with the volume of 200mL, and 1.07g (20 mmol) of ammonium chloride, 2.96g (20 mmol) of p-methoxy allylbenzene and 150mL of N, N-dimethylformamide are added; stirring and continuously introducing argon gas after the mixture is dissolved; taking an iron sheet with the surface area of 20cm 2 as a cathode and an anode, introducing 100mA current, and continuously electrolyzing for 4 hours at the temperature of 50 ℃; after the reaction, the solvent was removed under vacuum, 200mL of water was added, extraction was performed three times with 200mL of ethyl acetate, the organic phases were combined, the solvent was removed under vacuum, and the (E) -1-methoxy-4- (1-propenyl) benzene was obtained by distillation and purification.
The mass of the isomerism product (E) -1-methoxy-4- (1-propenyl) benzene is 2.87g, the yield is 97%, and the Z/E is 1/99.
Example 3
1.50G (10 mmol) of sodium iodide, 3.94g (20 mmol) of p-bromoallylbenzene, 50mL of acetonitrile and 50mL of water are added into a reaction tank with the volume of 200 mL; stirring until the mixture is dissolved; taking a platinum sheet with the surface area of 15cm 2 as a cathode and an anode, introducing 60mA current, and continuously electrolyzing for 2 hours at the temperature of 30 ℃; after the reaction, the solvent was removed under vacuum, 200mL of water was added, extraction was performed three times with 200mL of ethyl acetate, the organic phases were combined, the solvent was removed under vacuum, and the (E) -1-bromo-4- (1-propenyl) benzene was obtained by distillation and purification.
The mass of the isomerism product (E) -1-bromo-4- (1-propenyl) benzene is 3.86g, the yield is 98%, and the Z/E is 1/99.
Example 4
1.74G (10 mmol) of potassium sulfate, 1.30g (10 mmol) of 1, 4-dihydroxynaphthalene, 50mL of methylene chloride and 50mL of water are added into a reaction tank with the volume of 200 mL; stirring until the mixture is dissolved; taking graphite sheets with the surface area of 20cm 2 as a cathode and an anode, connecting the voltage of 20V, and continuously electrolyzing for 4 hours at the temperature of 0 ℃; after the reaction, the solvent was removed under vacuum, 200mL of water was added, extraction was performed three times with 200mL of ethyl acetate, the organic phases were combined, the solvent was removed under vacuum, and the 1, 2-dihydronaphthalene was obtained by distillation and purification.
The quality of the isomerism product 1, 2-dihydronaphthalene is 1.22g, and the yield is 94%.
From the above examples 1 to 4, the method of the invention has the advantages of mild reaction conditions, simple process, strong operability, good production safety and good environmental friendliness; the raw materials are cheap and easy to obtain, and the cost is low; and the product has high purity, high yield and stable quality, and is suitable for industrial production.
The above embodiments are only for illustrating the technical solution of the present invention, and are not limiting thereof; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may be modified or some technical features may be replaced with other technical solutions, which may not make the essence of the corresponding technical solutions deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims (10)

1. An electrochemical synthesis method of E-type styrene derivatives is characterized in that an aromatic compound with an allyl structure is isomerised into E-type styrene derivatives shown as formula II;
2. the method for electrochemical synthesis of an E-type styrene derivative according to claim 1, comprising the steps of:
And (3) adding an electrolyte solution into an electrochemical reaction tank, and electrolyzing by using an aromatic compound with an allyl structure shown in the formula I as a substrate in a constant-current mode or a constant-voltage mode while keeping the temperature of the solution constant, wherein the substrate generates free radical active species under the activation of an electrode to trigger chain isomerization, so that the E-type styrene derivative II is obtained.
3. The method for electrochemical synthesis of E-type styrene derivatives according to claim 2, wherein the substrate I is an aromatic compound having an allyl structure, the aromatic structure of which comprises a benzene ring structure or a group having aromaticity; the aromatic group comprises at least one of furyl, thienyl, pyridyl and naphthyl; the aromatic structure is provided with an electron withdrawing group or an electron donating group; the electron withdrawing group comprises at least one of an ester group, an amide group, an acyl group and halogen; the electron donating group comprises at least one of methoxy and amino; the R 1,R2,R3 may be alkyl, ester, amide, acyl with chain length between C 1～C10.
4. The method for electrochemical synthesis of E-type styrene derivatives according to claim 2, wherein the electrochemical reaction cell is a single cell or a double cell, and when the electrochemical reaction cell is a double cell, the cathode cell and the anode cell are separated by a cation exchange membrane or a glass sand core.
5. The method for electrochemical synthesis of E-styrene derivatives according to claim 2, wherein the electrodes in the step comprise at least one of metal sheet, glassy carbon, stainless steel or graphite; the metal sheet comprises at least one of iron, copper, nickel, cobalt, zinc, aluminum, magnesium, lead, silver and platinum.
6. The method for electrochemical synthesis of E-styrene derivatives according to claim 2, wherein the electrolyte solution in the step is selected from an organic solvent/electrolyte or water/electrolyte, wherein the organic solvent is selected from acetonitrile, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, tetrahydrofuran, dichloromethane, ethylene glycol dimethyl ether or a mixture of two or more thereof; the electrolyte is selected from tetraalkylammonium salt inorganic salt; the tetraalkylammonium salt comprises tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium perchlorate, tetrabutyltetrafluoroboric acid, tetrabutylammonium hexafluorophosphate, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium iodide, tetraethylammonium perchlorate, tetramethyltetrafluoroboric acid or at least one of sodium iodide, potassium sulfate, sodium chloride and sodium triflate.
7. The method according to claim 2, wherein the reaction temperature in the step is selected from any temperature between-30 and 200 ℃.
8. The method according to claim 2, wherein the current density in the step is between 0.01 and 1000mA cm -2 and the operating voltage is between 0.1 and 220V.
9. The method according to claim 2, wherein the substrate concentration in the step is between 0.01 and 7mol L -1.
10. The method of claim 2, wherein the concentration of the electrolyte solution in the step is between 0.001 and 1mol L -1.
CN202410408334.6A 2024-04-07 2024-04-07 Electrochemical synthesis method of E-type styrene derivative Pending CN118166369A (en)

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