CN115385835A - Synthetic method of selenium ester compound - Google Patents
Synthetic method of selenium ester compound Download PDFInfo
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- CN115385835A CN115385835A CN202210988198.3A CN202210988198A CN115385835A CN 115385835 A CN115385835 A CN 115385835A CN 202210988198 A CN202210988198 A CN 202210988198A CN 115385835 A CN115385835 A CN 115385835A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
- C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
The invention relates to the technical field of organic synthetic chemistry, in particular to a synthetic method of a selenium ester compound, which comprises the following reaction steps: in the presence of a photocatalyst, aromatic aldehyde and a diselenide compound are stirred and react under the irradiation of a light source under a certain temperature condition to obtain a selenate compound. Compared with the traditional synthesis method, the method has the advantages that the reaction condition is mild, and the reaction can be smoothly carried out at room temperature; the cheap and easily obtained starting raw materials are used, the substrate application range is wide, the yield is high, and the functional group compatibility is good; meanwhile, the method of the invention uses visible light as an energy source, and has the characteristics of low price, sustainability, green and environmental protection.
Description
Technical Field
The invention relates to the technical field of organic synthetic chemistry, in particular to a synthetic method of a selenium ester compound.
Background
Selenium is a trace element essential to human body and participates in important physiological processes of human body. And is also a powerful antioxidant which is helpful for eliminating redundant free radicals in the human body. Selenium-containing compounds are also important organic synthesis reagents, are often applied to various organic reactions, and can also be applied to research of material science and pharmacy. Thus, the synthesis of selenium-containing compounds has been of widespread interest to organic and medicinal chemists ((a) Nogueira, c.w.; zeni, g.; rocha, j.b.t., chem.rev.2004,104,6255-6286, (b) Hou, w.; xu, h., j.med.chem.2022,65, 4436-4456).
Among the various selenium-containing compounds, selenoate (selenoesster) is a non-essential class of compounds, which is widely present in natural compounds and is also a very important intermediate in organic synthesis. Chemists have therefore invested considerable effort in developing methods for the synthesis of selenium esters (Baldasari, L.L.; ludtke, D.S. Chem.Eur.J.2021,27, 8656-8667). In the reported methods for synthesizing selenium ester compounds, the addition of a selenium-containing anion compound to an acid anhydride, an acid chloride, a carboxylic acid, an aldehyde, or the like is generally used. However, these methods have some disadvantages, such as the use of metal reagents to generate selenium nucleophiles, the difficulty of treating the metal reagents, and the large environmental pollution. The reaction conditions are harsh, and the substrate compatibility is poor. Therefore, there is still a need to develop a new reaction system with simple operation, high safety, high yield, wide applicability and relatively green color to construct selenium ester compounds.
Disclosure of Invention
The present invention is directed to a method for synthesizing selenate compounds, so as to solve the problems of the background art.
In order to achieve the purpose, the invention provides the following technical scheme: a synthetic method of a seleno-ester compound comprises the following reaction steps: in an organic solvent, taking aromatic aldehyde with a structure shown in a formula (I) and diselenide with a structure shown in a formula (II) as reaction raw materials, reacting under the irradiation of visible light in the presence of a photocatalyst, decompressing reaction liquid to remove the solvent after the reaction is finished to obtain a crude product, and purifying the crude product by column chromatography to obtain a selenate compound with a structure shown in a formula (III);
the reaction equation is shown as follows:
wherein, the compound of formula (I) is aromatic aldehyde, ar is selected from naphthyl, furyl, thienyl, phenyl and phenyl substituted by one or more substituents selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl or trifluoromethoxy;
the compound shown in the formula (II) is diaryl diselenide or dialkyl diselenide, R1 is selected from C1-C10 straight-chain or branched-chain alkyl, benzyl and phenyl substituted by one or more substituent groups, and the substituent groups are selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl and hydroxyl.
Preferably, the molar ratio of the aromatic aldehyde having a structure shown in formula (I) to the diselenide having a structure shown in formula (II) is 1: 0.5-1: 1, preferably 1: 0.5.
Preferably, the irradiation light source for the reaction is one of sunlight, a fluorescent lamp and an LED lamp, preferably a fluorescent lamp.
Preferably, the catalyst of the reaction is Ir (ppy) 3 、Ir(p-CF 3 ppy) 3 、Ir(d-Fppy) 3 、[Ir{dFCF 3 ppy} 2 (bpy)]PF 6 、[Ir(dtbbpy)(ppy) 2 ](PF 6 ) 2 Preferably Ir (p-CF) 3 ppy) 3 。
Preferably, the organic solvent is at least one of dimethyl sulfoxide, N-dimethylformamide, dichloromethane, chloroform, ethyl acetate, acetonitrile, tetrahydrofuran and carbon tetrachloride, and dichloromethane is preferred.
Preferably, the reaction time is 10h to 30h.
Preferably, after the reaction is finished, the reaction solution is decompressed and concentrated, and the concentrate is separated by column chromatography, and a mixed solution of petroleum ether and ethyl acetate is used as an eluent, wherein the ratio of petroleum ether: the volume ratio of the ethyl acetate is (10-200): 1, collecting the eluent, and carrying out rotary evaporation on the solvent to obtain the selenate compound shown in the formula (III).
Compared with the prior art, the invention has the beneficial effects that:
(1) The method can be carried out at room temperature, and has the advantages of simple operation, mild reaction conditions, good functional group compatibility and high product yield.
(2) The invention uses visible light as an energy source, has the characteristics of low price, sustainability, environmental protection and the advantages of safety and easy operation.
(3) The invention uses cheap and easily obtained starting materials, can obtain the target product by only one step, and has good application potential.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides the following technical scheme: a synthetic method of a seleno-ester compound comprises the following reaction steps: the reaction steps are as follows: in an organic solvent, taking aromatic aldehyde with a structure shown in a formula (I) and diselenide with a structure shown in a formula (II) as reaction raw materials, reacting under the irradiation of visible light in the presence of a photocatalyst, decompressing reaction liquid to remove the solvent after the reaction is finished to obtain a crude product, and purifying the crude product by column chromatography to obtain a selenate compound with a structure shown in a formula (III);
the reaction equation is shown as follows:
wherein, in the compound of formula (I), ar is selected from naphthyl, furyl, thienyl, phenyl and phenyl substituted by one or more substituents selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl or trifluoromethoxy;
the compound of the formula (II) is diaryl diselenide or dialkyl diselenide, R1 is selected from C1-C10 straight-chain or branched-chain alkyl, benzyl and phenyl substituted by one or more substituent groups, and the substituent groups are selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl and hydroxyl;
the photocatalyst is Ir (p-CF) 3 ppy) 3 (ii) a The irradiation light source of the reaction is a fluorescent lamp; the organic solvent is dichloromethane.
Example 1:
the reaction equation is shown as follows:
a10 mL reaction tube containing a magnetic stirrer was charged with benzaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after the addition was completed, N was charged 2 Protection, a 23 watt white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube and reacted at room temperature for 20 hours, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (specification of silica gel: 200 mesh to 300 mesh, eluent petroleum ether/ethyl acetate = 100) to obtain 44 mg of the objective compound with a yield of 85%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.95–7.83(m,2H),7.65–7.58(m,3H),7.53–7.40(m,5H)； 13 C NMR(100MHz,CDCl 3 ):δ193.2,138.9,136.1,134.1,129.6,129.2,129.0,127.9,125.8.
example 2:
the reaction equation is shown as follows:
A10-mL reaction tube equipped with a magnetic stirrer was charged with 4-methylbenzaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after addition was charged with N 2 Protecting, placing a 23-watt white compact fluorescent lamp at a place 1 cm away from the reaction tube, reacting at room temperature for 20 hours, and rotating the organic phase after the reaction is finishedThe solvent was removed by an evaporator, and the residue was purified by a silica gel column (specification of silica gel 200 to 300 mesh, eluent petroleum ether/ethyl acetate = 80) to obtain 50 mg of the objective compound with a yield of 90%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.80(d,J＝8.4Hz,2H),7.60–7.55(m,2H),7.42–7.36(m,3H),7.25(d,J＝8.2Hz,2H),2.40(s,3H)； 13 C NMR(100MHz,CDCl 3 ):δ192.5,144.8,136.4,135.8,129.3,129.8,129.0,127.3,125.7,21.5.
example 3:
the reaction equation is shown as follows:
A10-mL reaction tube equipped with a magnetic stirrer was charged with 4-methoxybenzaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after addition was charged with N 2 Protection, a 23 w white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube and reacted at room temperature for 20 hours, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (specification of silica gel: 200 to 300 mesh, eluent petroleum ether/ethyl acetate = 100) to obtain 48 mg of the objective compound with a yield of 83%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.92–7.89(m,2H),7.63–7.57(m,2H),7.45–7.37(m,3H),6.99–6.94(m,2H),3.88(s,3H)； 13 C NMR(100MHz,CDCl 3 ):δ191.3,164.5,136.1,131.3,130.0,129.3,129.1,126.0,114.4,55.7.
example 4:
the reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 4-chlorobenzaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after the addition was completed, N was charged 2 After completion of the reaction, the organic phase was subjected to solvent removal by a rotary evaporator, and the residue was purified by a silica gel column (silica gel specification: 200 to 300 mesh, eluent petroleum ether/ethyl acetate = 110) to obtain 54 mg of the objective compound with a yield of 92%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.90–7.86(m,2H),7.62–7.56(m,2H),7.49–7.39(m,5H)； 13 C NMR(100MHz,CDCl 3 ):δ192.8,140.4,137.0,136.4,130.1,129.3,129.1,128.7,125.7.
example 5:
the reaction equation is shown as follows:
a10 mL reaction tube containing a magnetic stir bar was charged with 4-nitrobenzaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after addition was charged with N 2 Protection, a 23 watt white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube and reacted at room temperature for 20 hours, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (specification of silica gel: 200 mesh to 300 mesh, eluent petroleum ether/ethyl acetate = 50),
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ8.35(d,J＝8.2Hz,2H),8.10(d,J＝8.1Hz,2H),7.51–7.40(m,2H),7.31–7.25(m,3H)； 13 CNMR(100MHz,CDCl 3 ):δ192.1；151.1,143.3,136.5,131.5,129.7,128.2,125.2,124.1.
example 6:
the reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 2-furaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after addition was charged with N 2 After completion of the reaction, the organic phase was subjected to solvent removal by a rotary evaporator, and the residue was purified by a silica gel column (silica gel specification: 200 to 300 mesh, eluent petroleum ether/ethyl acetate = 80) to obtain 43 mg of the objective compound with a yield of 85%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.52-7.45(m,3H),7.33-7.26(m,3H),7.12-7.09(m,1H),6.49-6.43(m,1H)； 13 C NMR(100MHz,CDCl 3 ):δ182.0,151.8,147.0,136.8,129.7,129.5,125.0,115.6,113.2.
example 7:
the reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 2-thiophenecarboxaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after addition was charged with N 2 Protecting, placing 23W white compact fluorescent lamp at a distance of 1 cm from the reaction tube, reacting at room temperature for 20 hr, removing solvent from the organic phase by rotary evaporator, and purifying the residue with silica gel column (silica gel size of 200 mesh)About 300 mesh, eluent petroleum ether/ethyl acetate = 100) to give 49 mg of the target compound, in 92% yield,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.82(d,J＝4.0Hz,1H),7.65(d,J＝5.3Hz,1H),7.59–7.55(m,2H),7.40–7.38(m,3H),7.13(t,J＝4.6Hz,1H)； 13 C NMR(100MHz,CDCl 3 )δ183.2,142.5,136.1,133.0,131.9,129.1,128.7,127.8,125.4.
example 8:
the reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 1-naphthaldehyde (0.2 mmol), diphenyldiselenide (0.1 mmol), and Ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after addition was charged with N 2 Protection, a 23 watt white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube and reacted at room temperature for 20 hours, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (specification of silica gel: 200 mesh to 300 mesh, eluent petroleum ether/ethyl acetate = 90),
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ8.58(d,J＝8.4Hz,1H),8.21(d,J＝7.2Hz,1H),8.08(d,J＝8.4Hz,1H),7.93(d,J＝7.6Hz,1H),7.70–7.68(m,2H),7.63–7.47(m,6H)； 13 C NMR(100MHz,CDCl 3 ):δ195.5,136.4,136.2,133.9,133.7,129.5,129.1,128.5,128.4,128.3,127.3,127.3,127.0,125.5,124.7.
example 9:
the reaction equation is shown as follows:
a10 mL reaction tube containing a magnetic stirrer was charged with benzaldehyde (0.2 mmol), dimethyl diselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after addition was charged with N 2 Protection, a 23 watt white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube and reacted at room temperature for 20 hours, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (specification of silica gel: 200 mesh to 300 mesh, eluent petroleum ether/ethyl acetate =120 1) to obtain 32 mg of the objective compound with a yield of 81%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.90–7.81(m,3H)7.65–7.59(m,2H),2.42(s,3H)； 13 C NMR(100MHz,CDCl 3 ):δ195.0,139.2,134.0,129.5,127.8,5.9.
example 10:
the reaction equation is shown as follows:
a10 mL reaction tube containing a magnetic stirrer was charged with benzaldehyde (0.2 mmol), bis (4-chlorophenyl) diselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after the addition was completed, N was charged 2 After completion of the reaction, the organic phase was subjected to solvent removal by a rotary evaporator, and the residue was purified by a silica gel column (silica gel specification: 200 to 300 mesh, eluent petroleum ether/ethyl acetate = 100) to obtain 51 mg of the objective compound with a yield of 87%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.94–7.91(m,2H),7.62(d,J＝10.0Hz,1H),7.52–7.46(m,4H),7.40–7.36(m,2H)； 13 C NMR(100MHz,CDCl 3 ):δ192.9,138.8,137.6,136.7,135.0,130.0,129.5,127.6,124.3.
example 11:
the reaction equation is shown as follows:
a10 mL reaction tube containing a magnetic stirrer was charged with benzaldehyde (0.2 mmol), bis (4-methylphenyl) diselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after the addition was completed, N was charged 2 After completion of the reaction, the organic phase was subjected to solvent removal by a rotary evaporator, and the residue was purified by a silica gel column (silica gel specification: 200 to 300 mesh, eluent petroleum ether/ethyl acetate = 100) to obtain 51 mg of the objective compound with a yield of 92%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 )δ7.89(d,J＝7.4Hz,2H),7.65(t,J＝7.4Hz,1H),7.51(t,J＝7.3Hz,4H),7.26(d,J＝7.4Hz,2H),2.41(s,3H)； 13 C NMR(100MHz,CDCl 3 ):δ193.8,140.1,138.6,136.7,133.9,130.3,129.2,127.0,122.1,21.8.
example 12:
the reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with benzaldehyde (0.2 mmol), dithienyl diselenide (0.1 mmol), ir (p-CF) at room temperature 3 ppy) 3 (0.002 mmol), dichloromethane (2 ml), after the addition was completed, N was charged 2 Protecting, placing 23W white compact fluorescent lamp at a distance of 1 cm from the reaction tube, reacting at room temperature for 20 hours, removing solvent from the organic phase through a rotary evaporator after the reaction is finished, and purifying the residue with silica gel column (silica gel specification is 200 mesh ℃ -300 mesh, eluent petroleum ether/ethyl acetate = 80), to give 49 mg of the target compound, with a yield of 91%,
the nuclear magnetic spectrum data of the obtained product are as follows: 1 H NMR(400MHz,CDCl 3 ):δ7.91(d,J＝8.4Hz,2H),7.65–7.60(m,2H),7.55–7.50(m,2H),7.31–7.27(m,1H),7.19–7.15(m,1H)； 13 C NMR(100MHz,CDCl 3 ):δ192.6,137.7,137.1,134.0,132.8,129.0,127.9,127.5,119.0.
in summary, the present invention provides a method for synthesizing selenoate compound in photocatalyst Ir (p-CF) 3 ppy) 3 In the presence of visible light, aromatic aldehyde and diselenide are irradiated to react to obtain the selenate compound. The invention has cheap and easily obtained starting materials, mild reaction conditions and high reaction yield of the obtained product, thereby having good application prospect in organic synthesis and drug synthesis.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (5)
1. A synthetic method of a selenium ester compound is characterized by comprising the following steps: the reaction steps are as follows: in an organic solvent, taking aromatic aldehyde with a structure shown in a formula (I) and diselenide with a structure shown in a formula (II) as reaction raw materials, reacting under the irradiation of visible light in the presence of a photocatalyst, decompressing reaction liquid to remove the solvent after the reaction is finished to obtain a crude product, and purifying the crude product by column chromatography to obtain a selenate compound with a structure shown in a formula (III);
the reaction equation is shown as follows:
wherein, the compound of formula (I) is aromatic aldehyde, ar is selected from naphthyl, furyl, thienyl, phenyl and phenyl substituted by one or more substituents selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl or trifluoromethoxy;
the compound of the formula (II) is diaryl diselenide or dialkyl diselenide, R1 is selected from C1-C10 straight-chain or branched-chain alkyl, benzyl and phenyl substituted by one or more substituent groups, and the substituent groups are selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl and hydroxyl;
the photocatalyst is Ir (p-CF) 3 ppy) 3 (ii) a The irradiation light source of the reaction is a fluorescent lamp; the organic solvent is dichloromethane.
2. The method of claim 1, wherein the step of synthesizing the selenoate compound comprises the steps of: the molar ratio of the aromatic aldehyde with the structure shown in the formula (I) to the diselenide with the structure shown in the formula (II) is 1: 0.5-1: 1.
3. The method of claim 2, wherein the step of synthesizing the selenoate compound comprises the steps of: the molar ratio of the aromatic aldehyde with the structure shown in the formula (I) to the diselenide with the structure shown in the formula (II) is 1: 0.5.
4. The method of claim 1, wherein the step of synthesizing the selenoate compound comprises the steps of: the reaction time is 10-30 h.
5. The method of claim 1, wherein the step of synthesizing the selenoate compound comprises the steps of: after the reaction is finished, concentrating the reaction solution under reduced pressure, separating the concentrate by column chromatography, and taking a mixed solution of petroleum ether and ethyl acetate as an eluent, wherein the ratio of petroleum ether: the volume ratio of the ethyl acetate is (10-200): 1, collecting the eluent, and carrying out rotary evaporation on the solvent to obtain the selenate compound shown in the formula (III).
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