CN114920652A - Method for photocatalytic synthesis of 1-alkylstyrene derivatives - Google Patents
Method for photocatalytic synthesis of 1-alkylstyrene derivatives Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000001699 photocatalysis Effects 0.000 title claims description 19
- 238000003786 synthesis reaction Methods 0.000 title claims description 10
- 230000015572 biosynthetic process Effects 0.000 title claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000006243 chemical reaction Methods 0.000 claims abstract description 55
- 239000012074 organic phase Substances 0.000 claims abstract description 23
- 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 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 10
- -1 alkyl radicals Chemical class 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
- 238000003756 stirring Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000005303 weighing Methods 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 238000007865 diluting Methods 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 239000011941 photocatalyst Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 18
- 239000003208 petroleum Substances 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 239000011591 potassium Substances 0.000 claims description 9
- 238000004458 analytical method Methods 0.000 claims description 8
- 239000000203 mixture 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
- 230000008569 process Effects 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims 6
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 abstract description 17
- 230000002194 synthesizing effect Effects 0.000 abstract description 8
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 9
- 238000005937 allylation reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 5
- 238000007146 photocatalysis Methods 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- NZEDMAWEJPYWCD-UHFFFAOYSA-N 3-prop-2-enylsulfonylprop-1-ene Chemical compound C=CCS(=O)(=O)CC=C NZEDMAWEJPYWCD-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-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
- 150000002148 esters Chemical class 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
- 150000005837 radical ions Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid 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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Abstract
The invention provides a preparation method of a 1-alkylstyrene derivative, which comprises the following steps: s1: to a reaction tube with a stirrer was added 2-aryl allyl ether and photocatalyst Ir [ dF (CF) 3 )ppy] 2 (dtbbpy)PF 6 (ii) a S2: weighing a free radical precursor into the reaction tube after the operation of 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 solution with ethyl acetate and water, and extracting with ethyl acetate to obtain an organic phase; combining the organic phases, drying over anhydrous sodium sulfate, and filtering to obtain an organic phaseRemoving the solvent from the solution by a rotary evaporator; then carrying out column chromatography separation, and finally distilling by a rotary evaporator to obtain the product 1-alkylstyrene derivative. The invention develops a new method for modularly synthesizing 1-alkylstyrene derivatives by reacting allyl ether with alkyl radicals; the method has the advantages of wide substrate application range, good functional group compatibility, mild and efficient reaction conditions, simplicity and convenience in operation and the like.
Description
Technical Field
The invention relates to the field of photocatalytic synthesis, in particular to a method for synthesizing a 1-alkylstyrene derivative through photocatalysis.
Background
Allylation reactions involving free radicals are a common and convenient means of building olefins in organic synthesis. Common allylated acceptors are compounds such as allyl sulfone, allyl halide, etc., and such allylation reactions undergo radical addition and radical cleavage of leaving groups, which is a pure radical process:
in addition, the allylation reaction involving free radicals can also be a "free radical-ion" cross-reaction process. For example, with an allyl substituent as the radical acceptor, the reaction proceeds through a radical addition/one-electron reduction/1, 2-elimination process involving both radical and anion pathways. In this type of reaction, the cleavage of the C — O bond mainly involves the bond between the ester carbonyl carbon and the alkoxy oxygen:
in view of the simplicity of olefin synthesis in allylation, the development of novel allylation reaction around a free radical catalytic system, a free radical precursor and a free radical receptor still has important significance, and particularly the development of novel allylation reaction 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 of the prior art: provides a method for synthesizing 1-alkylstyrene derivatives by photocatalysis by using high-valence organic silicon as a free radical precursor and allyl ether as a free radical acceptor under the mild visible light irradiation condition without alkali and an additional reducing agent.
In order to solve the above problems, the present invention provides a method for photocatalytic synthesis of a 1-alkylstyrene derivative, comprising the steps of:
s1: to a reaction tube with a stirrer was added 2-aryl allyl ether and photocatalyst Ir [ dF (CF) 3 )ppy] 2 (dtbbpy)PF 6 ；
S2: weighing the radical precursor into the reaction tube after the operation of 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 solution with ethyl acetate and water, and extracting with ethyl acetate to obtain an organic phase; combining the organic phases, drying the organic phases by using anhydrous sodium sulfate, filtering the organic phases to obtain an organic phase solution, and removing the solvent by using a rotary evaporator; then carrying out column chromatography separation, and finally distilling by a rotary evaporator to obtain the product 1-alkylstyrene derivative.
Preferably, the 2-aryl allyl ether is 2-naphthyl propenyl methyl ether, and the radical precursor is an alkyl silicon radical precursor.
Preferably, the alkylsilicon 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.
Preferably, the molar ratio of the free radical precursor, Ir [ dF (CF3) ppy ]2(dtbbpy) PF6, 2-aryl allyl ether, dimethyl sulfoxide is 1 (0.01-0.03): 1.5-2.5): 400-450.
Preferably, in step S2, the irradiation conditions under blue light are: and (3) placing the reaction tube under a 9W blue LED lamp for irradiation, stirring at room temperature for reaction for 24-48h, and stopping the illumination reaction.
Preferably, in step S3, the eluent used for the column chromatography analysis is a mixture of petroleum ether and ethyl acetate.
Preferably, the volume ratio of the petroleum ether to the ethyl acetate in the mixed liquid of the petroleum ether and the ethyl acetate is 10: 1.
Preferably, in step S3, the length of the silica gel column in the column chromatography separation is 10 cm.
Preferably, in step S3, the conditions for combining the organic phases and 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.
Preferably, the reaction formula of the preparation method is as follows:
the invention has the beneficial effects that: the invention provides a novel method for modularly synthesizing 1-alkylstyrene derivatives through the reaction of allyl ether and alkyl radicals; the method has the advantages of wide substrate application range, good functional group compatibility, mild and efficient reaction conditions, simple and convenient operation and the like; provides a novel allylation reaction with mild reaction conditions, simple operation, good universality and high efficiency.
Detailed Description
The technical solutions of the present invention will be described clearly and completely below, and it should be apparent that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
Example one
The embodiment provides a method for synthesizing a 1-alkylstyrene derivative through photocatalysis, which comprises the following steps:
s1: a magneton is put into the reaction tube, and Ir [ dF (CF) is added 3 )ppy] 2 (dtbbpy)PF 6 (4.5mg,0.004mmol,0.02equiv), 2-phenylpropylene ethyl ether (64.8mg,0.4mmol,2.0 equiv);
s2: placing the reaction tube into a glove box, and weighing azomethylaniline bis (catechol) silicate-18-crown ether-6-potassium (130.8mg,0.2mmol,1.0equiv) in the glove box; taking out the reaction tube after being plugged by a rubber plug, adding dry dimethyl sulfoxide (6mL) under nitrogen, and sealing the rubber plug by a sealing film; the reaction tube is placed under a 9W blue light LED lamp for irradiation, and after stirring reaction at room temperature for 36 hours, the irradiation reaction is stopped;
s3: 6mL of water was added to the reaction mixture, which was extracted with ethyl acetate (4X 10mL), the organic phase was combined and washed with 5mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate and filtered, the filtrate was evaporated to remove the solvent, and then a mixture of petroleum ether and ethyl acetate (V) Petroleum ether ：V Acetic acid ethyl ester 15: 1) the target product 22.3mg is obtained by flash column chromatography, the yield is 50 percent, and the product is light yellow viscous liquid.
The reaction formula of the above reaction is as follows:
the target product is subjected to experimental analysis, and the analysis data are as follows:
1 H NMR(500MHz,CDCl 3 )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). 13 C NMR(126MHz,CDCl 3 )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 through photocatalysis, which comprises the following steps:
s1: a magneton is put into the reaction tube, and Ir [ dF (CF) is added 3 )ppy] 2 (dtbbpy)PF 6 (4.5mg,0.004mmol,0.02equiv), 2-naphthylpropenyl methyl ether (79.2mg,0.4mmol,2.0 equiv);
s2: placing the reaction tube in a glove box, and weighing cyclohexyl bis (catechol) silicate-18-crown ether-6-potassium (126.0mg,0.2mmol,1.0equiv) in the glove box; the reaction tube was stoppered with a rubber stopper, dried dimethyl sulfoxide (6mL) was added under nitrogen, and the rubber stopper was sealed with a sealing film. The reaction tube is placed under a 9W blue light LED lamp for irradiation, and after stirring reaction at room temperature for 36 hours, the irradiation reaction is stopped;
s3: the reaction mixture was extracted with ethyl acetate (4X 10mL) after adding 6mL of water, 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 a mixture of petroleum ether and ethyl acetate (V) Petroleum ether ：V Acetic acid ethyl ester 100: 1) flash column chromatography to obtain 30.0mg of target product with yield of 60% as white solid.
The reaction formula of the above reaction is as follows:
the target product is subjected to experimental analysis, and the analysis data is as follows:
1 H NMR(500MHz,CDCl 3 )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). 13 C NMR(126MHz,CDCl 3 )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 C 19 H 22 :273.1619,found 273.1615.
EXAMPLE III
The embodiment provides a method for synthesizing a 1-alkylstyrene derivative through photocatalysis, which comprises the following steps:
s1: a magneton is put into the reaction tube, and Ir [ dF (CF) is added 3 )ppy] 2 (dtbbpy)PF 6 (4.5mg,0.004mmol,0.02equiv), 2-naphthylpropenyl methyl ether (79.2mg,0.4mmol,2.0 equiv);
s2: the reaction tube was placed in a glove box, and ethyl bis (catechol) silicate-18-crown-6-potassium complex (115.2mg,0.2mmol,1.0equiv) was weighed in the glove box; the reaction tube was stoppered with a rubber stopper, dried dimethyl sulfoxide (6mL) was added under nitrogen, and the stopper was closed with a sealing film. The reaction tube is placed under a 9W blue light LED lamp for irradiation, and after stirring reaction at room temperature for 24 hours, the irradiation reaction is stopped;
s3: 6mL of water was added to the reaction mixture, which was extracted with ethyl acetate (4X 10mL), the organic phase was combined and washed with 5mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate and filtered, the filtrate was evaporated to remove the solvent, and then a mixture of petroleum ether and ethyl acetate (V) Petroleum ether ：V Ethyl acetate 100: 1) the target product 20.4mg is obtained by flash column chromatography, the yield is 52 percent, and the product is colorless transparent viscous liquid.
The reaction formula of the above reaction is as follows:
the target product is subjected to experimental analysis, and the analysis data is as follows:
1 H NMR(500MHz,CDCl 3 )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). 13 C NMR(126MHz,CDCl 3 )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.
as further illustrated by the above examples in conjunction with specific data, the present invention provides a novel method for synthesizing 1-alkylstyrene derivatives using high valent organosilicon as a radical precursor and allyl ether as a radical acceptor under mild visible light irradiation conditions without using a base and an additional reducing agent.
Although the present disclosure has been described above, the scope of the present disclosure is not limited thereto. Those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present disclosure, and such changes and modifications will fall within the scope of the present invention.
Claims (10)
1. A method for photocatalytic synthesis of 1-alkylstyrene derivatives, characterized in that it comprises the following steps:
s1: to a reaction tube with a stirrer was added 2-aryl allyl ether and photocatalyst Ir [ dF (CF) 3 )ppy] 2 (dtbbpy)PF 6 ；
S2: weighing the radical precursor into the reaction tube after the operation of 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 solution with ethyl acetate and water, and extracting with ethyl acetate to obtain an organic phase; combining the organic phases, drying the organic phases by using anhydrous sodium sulfate, filtering the organic phases to obtain an organic phase solution, and removing the solvent by using a rotary evaporator; then carrying out column chromatography separation, and finally distilling by a rotary evaporator to obtain the product 1-alkylstyrene derivative.
2. The photocatalytic synthesis method of 1-alkylstyrene derivatives according to claim 1, characterized in that the 2-arylallyl ether is 2-naphthylpropenyl methyl ether and the radical precursor is an alkylsilyl radical precursor.
3. The photocatalytic synthesis method of 1-alkylstyrene derivatives according to claim 2, wherein the alkylsilicon radical precursor is one of azomethylaniline bis (catechol) silicate-18-crown-6-potassium, cyclohexylbis (catechol) silicate-18-crown-6-potassium, ethylbis (catechol) silicate-18-crown-6-potassium.
4. The method for photocatalytic synthesis of 1-alkylstyrene derivatives according to claim 1, characterized in that the molar ratio of the radical precursors Ir [ dF (CF3) ppy ]2(dtbbpy) PF6, 2-aryl allyl ether, dimethyl sulfoxide is 1 (0.01-0.03): 1.5-2.5): 400-450.
5. The photocatalytic synthesis method for 1-alkylstyrene derivatives according to claim 1, wherein in step S2, the irradiation conditions under blue light are: and (3) placing the reaction tube under a 9W blue LED lamp for irradiation, stirring at room temperature for reaction for 24-48h, and stopping the illumination reaction.
6. The photocatalytic synthesis method of 1-alkylstyrene derivative according to claim 1, wherein in step S3, the eluent used for the column chromatography analysis is a mixture of petroleum ether and ethyl acetate.
7. The photocatalytic synthesis method of 1-alkylstyrene derivatives according to claim 6, wherein the volume ratio of petroleum ether to ethyl acetate in the mixed solution of petroleum ether and ethyl acetate is 10: 1.
8. The photocatalytic synthesis method of 1-alkylstyrene derivatives according to claim 1, wherein, in step S3, the length of the silica gel column in the column chromatographic separation is 10 cm.
9. The process for photocatalytic synthesis of 1-alkylstyrene derivatives according to claim 1, wherein in step S3, the conditions for combining the organic phases and drying with anhydrous sodium sulfate are: the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and filtered.
10. The process for the photocatalytic synthesis of 1-alkylstyrene derivatives according to any one of claims 1 to 9, characterized in that said preparation process has the general reaction formula:
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