CN114920652B - Method for synthesizing 1-alkylstyrene derivative by photocatalysis - Google Patents
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- 238000000034 method Methods 0.000 title claims description 16
- 230000001699 photocatalysis Effects 0.000 title claims description 13
- 230000002194 synthesizing effect Effects 0.000 title claims description 13
- 238000007146 photocatalysis Methods 0.000 title claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 150000003254 radicals Chemical class 0.000 claims abstract description 21
- 239000012074 organic phase Substances 0.000 claims abstract description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002243 precursor Substances 0.000 claims abstract description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 10
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical compound CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004440 column chromatography Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 238000007865 diluting Methods 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract description 3
- 239000011941 photocatalyst Substances 0.000 claims abstract description 3
- 238000005303 weighing Methods 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 20
- -1 2-naphthyl propenyl methyl ether Chemical group 0.000 claims description 15
- 239000003208 petroleum Substances 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 238000005286 illumination Methods 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 238000005937 allylation reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- FHRTUUJINXTKLO-UHFFFAOYSA-N 1-ethoxypropan-2-ylbenzene Chemical compound CCOCC(C)C1=CC=CC=C1 FHRTUUJINXTKLO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000037029 cross reaction Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000005837 radical ions Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of a 1-alkylstyrene derivative, which comprises the following steps: s1: adding 2-aryl allyl ether and a photocatalyst Ir (dF) (CF 3)ppy]2(dtbbpy)PF6; S2: weighing a free radical precursor into the reaction tube after the operation of the step S1, adding dried dimethyl sulfoxide, placing the reaction tube under blue light for irradiation and stirring at room temperature for reaction, S3: diluting the reaction liquid with ethyl acetate and water, then extracting with ethyl acetate to obtain an organic phase, merging the organic phases, drying with anhydrous sodium sulfate, filtering to obtain an organic phase solution, removing the solvent by a rotary evaporator, then carrying out column chromatography separation, and finally distilling by the rotary evaporator to obtain the product 1-alkylstyrene derivative.
Description
Technical Field
The invention relates to the field of photocatalytic synthesis, in particular to a method for synthesizing a 1-alkylstyrene derivative by photocatalysis.
Background
The allylation reaction involving free radicals is a common and simple means of constructing olefins in organic synthesis. Common allylation acceptors are compounds such as allyl sulfones, allyl halides, etc., and such allylation reactions undergo free radical addition and leaving radical cleavage processes, which are pure free radical processes:
Furthermore, the allylation reaction in which the free radicals participate may also be a "free radical-ion" cross-reaction process. For example, when allyl-substituted esters are used as radical acceptors, the reaction undergoes radical addition/single electron reduction/1, 2-elimination processes involving radical and anion pathways. In this type of reaction, cleavage of the c—o bond involves mainly the bond between the ester carbonyl carbon and the alkoxy oxygen:
in view of the simplicity of synthesizing olefin by allylation, the development of novel allylation still has important significance around a free radical catalytic system, a free radical precursor and a free radical acceptor, and particularly, the development of novel allylation with mild reaction conditions, simple operation, good universality and high efficiency is more important.
Disclosure of Invention
The technical problem to be solved by the invention is to overcome the defects in the prior art: a method for synthesizing 1-alkylstyrene derivatives by photocatalysis without alkali and external reducing agent under the condition of mild visible light irradiation by taking high-valence organosilicon as a free radical precursor and allyl ether as a free radical acceptor is provided.
In order to solve the problems, the invention provides a method for synthesizing 1-alkylstyrene derivatives by photocatalysis, which comprises the following steps:
S1: 2-arylallyl ether and a photocatalyst Ir [ dF (CF 3)ppy]2(dtbbpy)PF6;
s2: weighing a free radical precursor into the reaction tube after the operation of the step S1; adding dry dimethyl sulfoxide; the reaction tube is placed under blue light for irradiation and stirred at room temperature for reaction;
S3: diluting the reaction solution with ethyl acetate and water, and extracting with ethyl acetate to obtain an organic phase; the organic phases are combined and dried by anhydrous sodium sulfate, and then filtered to obtain an organic phase solution, and the solvent is removed by a rotary evaporator; then column chromatography separation is carried out, and finally the product 1-alkylstyrene derivative is obtained by distillation through a rotary evaporator.
Preferably, the 2-arylallyl ether is 2-naphthylpropenyl methyl ether, and the radical precursor is an alkylsilyl radical precursor.
As a preferable scheme, the alkyl silicon free radical precursor is one of azomethylaniline bis (catechol) silicate-18-crown ether-6-potassium, cyclohexyl bis (catechol) silicate-18-crown ether-6-potassium and ethyl bis (catechol) silicate-18-crown ether-6-potassium.
As a preferred scheme, the molar ratio of the free radical precursor, ir (dF (CF 3) ppy ]2 (dtbbpy) PF6, 2-aryl allyl ether and dimethyl sulfoxide is 1 (0.01-0.03): 1.5-2.5): 400-450.
As a preferable mode, in the step S2, the conditions of the irradiation under blue light are as follows: the reaction tube is placed under a blue LED lamp with the power of 9W for irradiation, and the illumination reaction is stopped after stirring reaction for 24-48 hours at room temperature.
In a preferred embodiment, in the step S3, the eluting agent used for the column chromatography is a mixture of petroleum ether and ethyl acetate.
As a preferable scheme, the volume ratio of petroleum ether to ethyl acetate in the petroleum ether and ethyl acetate mixed solution is 10:1.
Preferably, in the step S3, the length of the silica gel column in the column chromatography separation is 10cm.
As a preferable mode, in the step S3, the conditions for drying the combined organic phases with anhydrous sodium sulfate are as follows: the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and filtered.
As a preferred scheme, the reaction general formula of the preparation method is as follows:
the beneficial effects of the invention are as follows: the present invention provides a novel method for modularly synthesizing 1-alkylstyrene derivatives by the reaction of allyl ether and alkyl radicals; the invention has the advantages of wide substrate application range, good functional group compatibility, mild and efficient reaction conditions, simple operation and the like; provides a novel allylation reaction with mild reaction conditions, simple operation, good universality and high efficiency.
Detailed Description
The following description of the present invention will be made clearly and fully, and it is apparent that the embodiments described are some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The embodiment provides a method for synthesizing a 1-alkylstyrene derivative by photocatalysis, which comprises the following steps:
S1: to the reaction tube was placed a magneton, ir [ dF (CF 3)ppy]2(dtbbpy)PF6 (4.5 mg, 0.04 mmol,0.02 equiv.), 2-phenylpropylethyl ether (64.8 mg,0.4mmol,2.0 equiv.);
s2: the reaction tube was placed in a glove box, and azomethylaniline bis (catechol) silicate-18-crown-6-potassium (130.8 mg,0.2mmol,1.0 equiv) was weighed in the glove box; taking out the rubber plug for the reaction tube, adding dry dimethyl sulfoxide (6 mL) under nitrogen, and sealing the rubber plug with a sealing film; the reaction tube is arranged under a blue light LED lamp with the power of 9W for irradiation, and after stirring reaction for 36 hours at room temperature, the illumination reaction is stopped;
S3: the reaction mixture was added with 6mL of water, extracted with ethyl acetate (4×10 mL), the organic phase was combined and washed with 5mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate, and then filtered, the solvent was removed by rotary evaporation of the filtrate, and then, the objective product was 22.3mg by flash column chromatography using a mixture of petroleum ether and ethyl acetate (V Petroleum ether ：V Acetic acid ethyl ester =15:1), with a yield of 50% as a pale yellow viscous liquid.
The reaction formula of the above reaction is as follows:
The target product was subjected to experimental analysis with the following analysis data:
1H NMR(500MHz,CDCl3)δ7.487.47(m,2H),7.36-7.27(m,3H),5.52(d,J＝1.2Hz,1H),5.35(d,J＝1.4Hz,1H),4.37(d,J＝1.2Hz,2H),3.56-3.54(m,2H),1.23(t,J＝7.0Hz,3H).13C NMR(126MHz,CDCl3)δ144.5,138.9,128.3,127.7,126.0,114.0,72.5,65.6,15.2.
example two
The embodiment provides a method for synthesizing a 1-alkylstyrene derivative by photocatalysis, which comprises the following steps:
s1: to the reaction tube was placed a magneton, ir [ dF (CF 3)ppy]2(dtbbpy)PF6 (4.5 mg, 0.04 mmol,0.02 equiv.), 2-naphthylpropenyl methyl ether (79.2 mg,0.4mmol,2.0 equiv.);
s2: the reaction tube was placed in a glove box, and cyclohexylbis (catechol) silicate-18-crown-6-potassium (126.0 mg,0.2mmol,1.0 equiv) was weighed in the glove box; the reaction tube was taken out with a rubber stopper, dried dimethyl sulfoxide (6 mL) was added under nitrogen, and the rubber stopper was sealed with a sealing film. The reaction tube is arranged under a blue light LED lamp with the power of 9W for irradiation, and after stirring reaction for 36 hours at room temperature, the illumination reaction is stopped;
s3: the reaction solution was added with 6mL of water, extracted with ethyl acetate (4×10 mL), the organic phase was combined and washed with 5mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate and filtered, the solvent was removed by rotary evaporation of the filtrate, and then 30.0mg of the objective product was obtained by flash column chromatography using a mixture of petroleum ether and ethyl acetate (V Petroleum ether ：V Acetic acid ethyl ester =100:1) in 60% yield as a white solid.
The reaction formula of the above reaction is as follows:
The target product was subjected to experimental analysis with the following analysis data:
1H NMR(500MHz,CDCl3)δ7.86-7.78(m,4H),7.60-7.58(m,1H),7.50-7.44(m,2H),5.42(d,J＝1.7Hz,1H),5.13(d,J＝1.7Hz,1H),2.52(d,J＝7.1Hz,2H),1.76-1.59(m,5H),1.41-1.35(m,1H),1.16-1.09(m,3H),0.97-0.90(m,2H).13C NMR(126MHz,CDCl3)δ147.0,138.7,133.3,132.7,128.1,127.7,127.5,126.0,125.7,124.9,124.8,114.1,43.7,35.8,33.2,26.5,26.2.HRMS(ESI)[M+Na]+:calculated for C19H22:273.1619,found 273.1615.
example III
The embodiment provides a method for synthesizing a 1-alkylstyrene derivative by photocatalysis, which comprises the following steps:
s1: to the reaction tube was placed a magneton, ir [ dF (CF 3)ppy]2(dtbbpy)PF6 (4.5 mg, 0.04 mmol,0.02 equiv.), 2-naphthylpropenyl methyl ether (79.2 mg,0.4mmol,2.0 equiv.);
S2: the reaction tube was placed in a glove box, and ethyl bis (catechol) silicate-18-crown-6-potassium (115.2 mg,0.2mmol,1.0 equiv) was weighed in the glove box; the reaction tube was taken out with a rubber stopper, dried dimethyl sulfoxide (6 mL) was added under nitrogen, and the rubber stopper was sealed with a sealing film. The reaction tube is arranged under a blue light LED lamp with the power of 9W for irradiation, and after stirring reaction for 24 hours at room temperature, the illumination reaction is stopped;
S3: the reaction mixture was added with 6mL of water, extracted with ethyl acetate (4×10 mL), the organic phase was combined and washed with 5mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by rotary evaporation of the filtrate, and then 20.4mg of the objective product was obtained by flash column chromatography using a mixture of petroleum ether and ethyl acetate (V Petroleum ether ：V Acetic acid ethyl ester =100:1), with a yield of 52% as a colorless transparent viscous liquid.
The reaction formula of the above reaction is as follows:
The target product was subjected to experimental analysis with the following analysis data:
1H NMR(500MHz,CDCl3)δ7.86-7.60(m,4H),7.62-7.59(m,1H),7.50-7.44(m,2H),5.48-5.44(m,1H),5.19-5.18(m,1H),2.64-2.61(m,2H),1.60-1.52(m,2H),0.98(t,J＝7.3Hz,3H).13C NMR(126MHz,CDCl3)δ148.3,138.7,133.4,132.7,128.1,127.7,127.5,126.0,125.7,124.7(4),124.6(5),112.8,37.4,21.4,13.8.
The present invention is further illustrated by the above examples in combination with specific data, which provide a novel method for synthesizing 1-alkylstyrene derivatives using high-valent silicones as radical precursors and allyl ethers as radical acceptors under mild irradiation with visible light without the need for bases and external reducing agents.
Although the present disclosure is described above, the scope of protection of the present disclosure is not limited thereto. Various changes and modifications may be made by one skilled in the art without departing from the spirit and scope of the disclosure, and these changes and modifications will fall within the scope of the invention.
Claims (4)
1. A method for photocatalytic synthesis of 1-alkylstyrene derivatives, comprising the steps of:
S1: 2-arylallyl ether and a photocatalyst Ir [ dF (CF 3)ppy]2(dtbbpy)PF6;
s2: weighing a free radical precursor into the reaction tube after the operation of the step S1; adding dry dimethyl sulfoxide; the reaction tube is placed under blue light for irradiation and stirred at room temperature for reaction;
S3: diluting the reaction solution with ethyl acetate and water, and extracting with ethyl acetate to obtain an organic phase; the organic phases are combined and dried by anhydrous sodium sulfate, and then filtered to obtain an organic phase solution, and the solvent is removed by a rotary evaporator; then column chromatography separation is carried out, and finally, a product 1-alkylstyrene derivative is obtained through distillation by a rotary evaporator;
the 2-aryl allyl ether is 2-naphthyl propenyl methyl ether, and the free radical precursor is an alkyl silicon free radical precursor;
The alkyl silicon free radical precursor is one of cyclohexyl bis (catechol) silicate-18-crown ether-6-potassium and ethyl bis (catechol) silicate-18-crown ether-6-potassium;
When the alkyl silicon radical precursor is cyclohexyl bis (catechol) silicate-18-crown ether-6-potassium, the structural formula of the 1-alkylstyrene derivative is ；
When the alkyl silicon radical precursor is ethyl bis (catechol) silicate-18-crown ether-6-potassium, the structural formula of the 1-alkylstyrene derivative is；
The molar ratio of the free radical precursor to Ir [ dF (CF 3)ppy]2(dtbbpy)PF6, 2-arylallyl ether and dimethyl sulfoxide is 1:0.01-0.03:1.5-2.5:400-450);
In the step S2, the conditions of the irradiation under blue light are as follows: the reaction tube is placed under a blue LED lamp with the power of 9W for irradiation, and the illumination reaction is stopped after stirring reaction for 24-48 hours at room temperature.
2. The method for synthesizing a 1-alkylstyrene derivative by photocatalysis according to claim 1, wherein in the step S3, the eluting agent used for the column chromatography separation is a mixed solution of petroleum ether and ethyl acetate.
3. The method for synthesizing the 1-alkylstyrene derivative by photocatalysis according to claim 2, which is characterized in that the volume ratio of petroleum ether to ethyl acetate in the mixed solution of petroleum ether and ethyl acetate is 10:1.
4. The method for photocatalytic synthesis of 1-alkylstyrene derivatives as set forth in claim 1, wherein in the step S3, the condition of combining the organic phases and drying with anhydrous sodium sulfate is: the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and filtered.
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| CN114105738A (en) * | 2021-11-24 | 2022-03-01 | 宁波工程学院 | Method for photocatalytic synthesis of alkyl alkenyl ether |
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| AU2003272349A1 (en) * | 2002-09-13 | 2004-04-30 | Yale University | Enantioselective amination and etherification |
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| CN1303382A (en) * | 1998-05-29 | 2001-07-11 | 陶氏化学公司 | Epoxidation process for aryl allyl ethers |
| JP2004115506A (en) * | 2002-09-05 | 2004-04-15 | Mitsubishi Chemicals Corp | Method for producing allyl compound |
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