A method for synthesizing (E)-vinyl selenol sulfone compounds using organic semiconductor g-C3N4 as catalyst

Abstract

The present invention provides a method for catalytic synthesis of organic semiconductor g-C3N4 ( E The invention relates to the technical field of organic synthesis. The invention uses selenium sulfonate and alkyne as reaction substrates, uses graphite phase carbon nitride g-C3N4 prepared by thermal polycondensation of urea as catalyst, and reacts freely in an organic solvent under light conditions to obtain ( E )-vinyl selenol sulfone compounds. The present invention is ( E The synthesis of )-vinyl selenolsulfone compounds provides a new pathway for preparing alkylaryl alkynes using this synthetic route, which offers mild reaction conditions and high yields. This invention utilizes the conveniently tunable and recyclable organic semiconductor g-C3N4 as a heterogeneous photocatalyst to achieve atom transfer radical addition reactions of alkynes in a metal-free environment, enabling precise control of the reaction's stereoselectivity and regioselectivity, and has promising application potential.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and in particular to a method for synthesizing (E)-vinyl selenol sulfone compounds by catalysis of an organic semiconductor g-C3N4. Background Art

[0002] Organoselenides are important compounds with a wide range of applications in chemistry, biology, medicine, and materials science. They exhibit pharmacological effects such as antitumor, antiviral, and anti-inflammatory properties. (J. Med. Chem. 2022, 65, 6, 4436–4456) Since alkenyl selenides are useful synthetic scaffolds and exhibit biological activity, and alkenyl sulfones are unique building blocks in biomolecules and useful synthetic intermediates, the synthesis of olefins containing both sulfonyl and selenium functional groups is crucial as reactants or intermediates in organic and pharmaceutical synthesis reactions, and is of great significance in the construction of complex molecules. The primary challenge lies in achieving stereoselective synthesis.

[0003] Under certain conditions, the C-Se bond can be cleaved with high selectivity, making the difunctionalization of alkynes an effective method for the regio- and stereoselective synthesis of tri- and tetrasubstituted alkenes. (E)-Vinyl selenolsulfone compounds serve as the synthetic backbones for this type of reaction, possessing certain biological activities and serving as important organic synthesis intermediates. For example, they serve as synthetic intermediates for the quinolizidine alkaloid (-)-lasubine. (Org. Lett. 2002, 4, 10, 1779–1781)

[0004] Existing publicly available methods for preparing (E)-vinyl selenolsulfone compounds primarily include (a) preparation from selenosulfonates and alkynes; (b) preparation from arylsulfonylhydrazides, selenoethers, and alkynes; (c) preparation from aryldiazonium salts, selenoethers, and alkynes; and (d) preparation from sulfonyl chlorides, selenoethers, and alkynes. However, these methods have drawbacks, such as the need for potentially explosive free radical initiators and oxidants, harsh reaction conditions, the difficulty of separating transition metals and rare noble metals from the reaction mixture as catalysts, and the difficulty of large-scale production due to the use of noble metals.

[0005] Given the potential importance of (E)-vinyl selenolsulfone compounds as versatile synthetic intermediates and pharmaceutically relevant molecules, it is necessary to develop a novel, green, photocatalytic synthesis method using heterogeneous catalysts (organic semiconductor catalysts) that is highly regio- and stereoselective, easy to operate, broadly applicable, and requires mild reaction conditions. The organic semiconductor graphitic carbon nitride (g-C3N4) is a heterogeneous photocatalyst, but there are no reports of using semiconductor carbon nitride as a catalyst for the synthesis of (E)-vinyl selenolsulfone compounds. Summary of the Invention

[0006] The main purpose of the present invention is to provide a method for synthesizing (E)-vinyl selenol sulfone compounds by catalysis of organic semiconductor g-C3N4, which has the advantages of being green and environmentally friendly, simple and safe to operate, mild reaction conditions, good substrate compatibility, and high target yield.

[0007] A (E)-vinyl selenol sulfone compound, the general structural formula of which is:

[0008]

[0009] To achieve the above objectives, the present invention proposes a method for synthesizing (E)-vinyl selenolsulfone compounds using an organic semiconductor g-C3N4 as a catalyst, comprising the following steps: using selenosulfonate and alkyne as reaction substrates and g-C3N4 prepared by thermal polycondensation of urea as a catalyst, allowing a free reaction to occur in an organic solvent under light conditions, and obtaining the (E)-vinyl selenolsulfone compounds by filtration, recrystallization, or chromatography purification;

[0010] The chemical equation is shown below:

[0011]

[0012] Wherein, the compound of formula (I) is selenosulfonate, R 1 Selected from C1~C 12 a linear or branched alkyl group, a cyclopropane group, a butyronitrile group, a trifluoromethyl group, a naphthyl group, a benzofuranyl group, a pyridyl group, a thienyl group, a phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of a methyl group, a methoxy group, a phenoxy group, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, a bromomethyl group, an acetamido group, or a tert-butyl group;

[0013] R 2 Selected from C1~C 10 a linear or branched alkyl group, a C3-C6 cycloalkyl group, a naphthyl group, an indenyl group, a pyridyl group, a thienyl group, a cyclohexanone group, a benzyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, a phenylpentyl group, a phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a trifluoromethoxy group, a hydroxyl group, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, an aldehyde group, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group;

[0014] The compound of formula (II) is an alkyne, R 3 Selected from C1~C 16a linear or branched alkyl group, a C3-C6 cycloalkyl group, a cyclohexenyl group, a chloromethyl group, a chloroethyl group, a chloropropyl group, a chlorobutyl group, an ethyl ketone group, a dimethylaminomethyl group, a cyano group, a naphthyl group, a pyridyl group, a pyrrolyl group, a quinolyl group, a thienyl group, a methyl acetate group, a methyl benzoate group, a benzoic acid group, a methoxymethyl group, a phenoxymethyl group, a p-methylphenoxymethyl group, a benzyloxyethyl group, a benzyloxypropyl group, a benzyl group, a phenethyl group, a phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of a methoxy group, a trifluoromethoxy group, a methyl formate group, an ethynyl group, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, a trifluoromethoxy group, an aldehyde group, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

[0015] The technical solution of the present invention provides a new route for the synthesis of vinyl selenol sulfone compounds, and the yield of vinyl selenol sulfone compounds prepared by the above synthesis route is high.

[0016] Furthermore, the selenosulfonate includes at least one of aryl-substituted selenosulfonate, heteroaryl-substituted selenosulfonate, and alkyl-substituted selenosulfonate.

[0017] Furthermore, the alkyne includes at least one of an aryl alkyne compound, a heteroaryl alkyne compound, and an alkyl alkyne compound.

[0018] Furthermore, the organic solvent includes at least one of dimethyl sulfoxide, dichloromethane, ethyl acetate, acetonitrile, dimethylformamide, tetrahydrofuran, n-hexane, 1,4-dioxane, diethyl ether, and carbon tetrachloride.

[0019] Furthermore, the lighting conditions are sunlight, fluorescent lamp, white LED lamp, and blue LED lamp.

[0020] Furthermore, the lighting condition is blue LED light.

[0021] Furthermore, the blue LED light is 24W.

[0022] Furthermore, stirring is performed under the light conditions, and the stirring time is 1 hour to 20 days.

[0023] Furthermore, the stirring time is 1h-120h.

[0024] Furthermore, the reaction temperature is -78°C to 100°C.

[0025] Furthermore, the reaction temperature is room temperature or -20°C.

[0026] Furthermore, the molar ratio of the alkyne to the selenosulfonate is 1:(0.2-4.0).

[0027] Furthermore, the molar ratio of the alkyne to the g-C3N4 is 1:(0.4-2.0).

[0028] Furthermore, the alkyne is an aromatic alkyne compound, and the molar ratio of the alkyne to the selensulfonate is 1:(0.2-4.0); the molar ratio of the alkyne to the g-C3N4 is 1:(0.4-2.0).

[0029] Furthermore, the preparation method of g-C3N4 is as follows: (1) adding urea to a crucible with a lid, heating the reaction to 540-560°C for 3.5-4.5h to obtain a yellow solid, and cooling to room temperature; (2) further heating the yellow solid in an open crucible to 490-510°C for 1.5-2.5h to obtain g-C3N4.

[0030] Furthermore, the preparation method of g-C3N4 is as follows: (1) adding urea to a crucible with a lid, heating the reaction to 550°C for 4 hours to obtain a yellow solid, and cooling to room temperature; (2) further heating the yellow solid to 500°C in an open crucible for 2 hours to obtain g-C3N4.

[0031] Furthermore, the heating rate of the heating reaction in step (1) is 2.5°C / min; and the heating rate of the further heating reaction in step (2) is 5°C / min.

[0032] Numerous experiments have shown that the g-C3N4 prepared in the present invention can provide a large number of photocatalytic reaction sites in the reaction system of the present invention, exhibiting high photocatalytic activity and stability, and having a catalytic effect superior to commercially available g-C3N4. Furthermore, the preparation method is simple, reproducible, easy to operate, and has a low preparation cost. The g-C3N4 prepared in the present invention has the highest quantum efficiency under 24W blue LED light.

[0033] Compared with the prior art, the advantages and beneficial effects of the present invention are:

[0034] (1) The present invention proposes for the first time a method for preparing (E)-vinyl selenolsulfone compounds using selensulfonate and alkyne as reaction substrates and graphite phase carbon nitride g-C3N4 prepared by thermal polycondensation of urea as a catalyst.

[0035] (2) The present invention utilizes the unique photophysical properties of organic semiconductor graphite phase carbon nitride g-C3N4 as a heterogeneous photocatalyst, and the synthetic route prepares (E)-vinyl selenol sulfone compounds with high yield, and the yield of the target product can reach 90%. In the system of the present invention, g-C3N4 has excellent chemical and thermal stability. At the same time, g-C3N4 is easy to separate from the reaction system and can be recycled many times. The present invention utilizes convenient, adjustable and recyclable organic semiconductor g-C3N4 as a heterogeneous photocatalyst to realize the atom transfer radical addition (ATRA) reaction of alkynes under metal-free conditions, thereby achieving precise control of the reaction stereoselectivity and regioselectivity.

[0036] (3) The reaction conditions of the present invention are mild, and the reaction can be carried out at room temperature. The reaction can also achieve a high yield at low temperature and normal pressure.

[0037] (4) The present invention achieves regio- and stereoselective synthesis of complex functionalized molecules of trisubstituted / tetrasubstituted alkenes and has good application potential.

[0038] (5) The g-C3N4 prepared in the present invention can provide more photocatalytic reaction sites in the reaction system of the present invention, has high photocatalytic activity and high photocatalytic stability, and the preparation method is simple, reproducible, easy to operate, and conducive to reducing costs. DETAILED DESCRIPTION

[0039] To better illustrate the objectives, technical solutions, and advantages of the present invention, the present invention will be further described below through specific embodiments. The described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by professionals in this field without creative work are within the scope of protection of the present invention.

[0040] Unless otherwise specified, the specific experimental methods and equipment involved in the following examples are all conventional methods or carried out according to the conditions recommended by the manufacturer's instructions.

[0041] The preparation method of g-C3N4 in the following examples is as follows: (1) adding urea to a crucible with a lid, heating the mixture to 550°C at a heating rate of 2.5°C / min for 4 h to obtain a yellow solid, and cooling the mixture to room temperature; (2) heating the yellow solid to 500°C in an open crucible at a heating rate of 5°C / min for 2 h to obtain g-C3N4.

[0042] In the examples of the present invention, the yield of the synthesized (E)-vinyl selenol sulfone compounds was investigated, and the yield was calculated as follows:

[0043] Yield = (actual yield / theoretical yield) * 100%

[0044] Among them, theoretical yield = total moles of raw materials added × relative molecular mass of target product.

[0045] Example 1

[0046] Synthesis of methyl(E)-4-(1-(phenylselanyl)-2-tosylvinyl)benzoate

[0047] The chemical structural formula is:

[0048]

[0049] Phenylseleno-p-toluenesulfonate (0.40 mmol), carbon nitride (0.18 mmol), methyl 4-ethynylbenzoate (0.20 mmol), and anhydrous DCM (1.0 mL) were added sequentially to a reaction flask under argon atmosphere. The reaction mixture was stirred at -20°C under 24W blue LED illumination for 17 hours. The reaction mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was evaporated under reduced pressure and purified by chromatography to obtain the desired product as a white solid in a 90% yield.

[0050] 1 H NMR(400MHz,Chloroform-d)δ:7.94(d,J=8.3Hz,2H),7.56(d,J=6.7Hz,2H),7.44(t,J=7.3Hz,1H),7.38(t,J=7.2H z,2H),7.33(d,J=8.3Hz,2H),7.25(d,J=8.4Hz,2H),7.14(d,J=8.1Hz,2H),6.19(s,1H),3.94(s,3H),2.38(s,3H); 13 C NMR(101MHz,Chloroform-d)δ:166.55,155.59,144.10,139.47,138.72,136.69,136.05,130.72,130 .39,130.34,129.96,129.58,129.13,128.95,128.59,127.80,127.51,126.49,126.43,52.40,21.67.

[0051] Example 2

[0052] Synthesis of (E)-2-(phenylselanyl)-3-tosylallyl acetate

[0053] The chemical structural formula is:

[0054]

[0055] Phenylseleno-p-toluenesulfonate (0.40 mmol), carbon nitride (0.16 mmol), propargyl acetate (0.20 mmol), and anhydrous DMSO (1.0 mL) were added sequentially to a reaction flask under argon atmosphere. The reaction mixture was stirred at -20°C under blue LED illumination for 88 h. The reaction mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was evaporated under reduced pressure and purified by column chromatography to obtain the desired product as a white solid in a 71% yield.

[0056] 1 H NMR(400MHz,Chloroform-d)δ:7.69(d,J=8.2Hz,2H),7.50(d,J=6.7Hz,2H),7.44(t,J=7.3Hz,1H),7. 41–7.34(m,2H),7.30(d,J=8.1Hz,2H),5.70(s,1H),5.48(d,J=1.8Hz,2H),2.41(s,3H),2.13(s,3H); 13 C NMR (101MHz, Chloroform-d) δ: 169.97, 156.04, 144.43, 138.50, 137.02, 130.43, 130.38, 130.00, 127.18, 124.95, 123.90, 62.42, 21.72, 20.65.

[0057] Example 3

[0058] Synthesis of (E)-phenyl(3-phenyl-1-tosylprop-1-en-2-yl)selane

[0059] The chemical structural formula is:

[0060]

[0061] Phenylseleno-p-toluenesulfonate (0.40 mmol), carbon nitride (0.17 mmol), 3-phenyl-1-propyne (0.20 mmol), and anhydrous DMSO (1.0 mL) were added sequentially to a reaction flask under argon atmosphere. The reaction mixture was stirred at -20°C under blue LED illumination for 88 hours. The reaction mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was evaporated under reduced pressure and purified by chromatography to obtain the desired product as a white solid in 85% yield.

[0062] 1H NMR(400MHz,Chloroform-d)δ:7.62(d,J=8.3Hz,2H),7.43(d,J=6.7Hz,2H),7.38(d,J=7.3Hz,1H), 7.32(t,J=7.3Hz,2H),7.28–7.23(m,5H),7.19–7.16(m,2H),5.98(s,1H),4.29(s,2H),2.40(s,3H); 13 C NMR(101MHz,Chloroform-d)δ:159.18,144.12,139.39,136.81,136.65,130.18, 130.02,129.94,129.35,128.62,127.23,127.17,126.29,125.14,38.44,21.71.

[0063] Example 4

[0064] Synthesis of (E)-4-(1-(phenylselanyl)-2-tosylvinyl)quinoline

[0065] The chemical structural formula is:

[0066]

[0067] Phenylseleno-p-toluenesulfonate (0.40 mmol), carbon nitride (0.15 mmol), 4-ethynylquinoline (0.20 mmol), and anhydrous DCM (1.0 mL) were added sequentially to a reaction flask under argon atmosphere. The reaction mixture was stirred at -20°C under blue LED illumination for 27.5 hours. The reaction mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was evaporated under reduced pressure and purified by chromatography to obtain the desired product as a white solid in 85% yield.

[0068] 1 H NMR(400MHz,Chloroform-d)δ:8.79(d,J=4.4Hz,1H),8.02(d,J=8.2Hz,1H),7.65(ddd,J=11.8,7.6,2.4Hz,2H),7.54(d,J =6.8Hz,2H),7.45–7.38(m,2H),7.34(t,J=7.4Hz,2H),7.15–7.09(m,3H),6.87(d,J=8.0Hz,2H),6.51(s,1H),2.22(s,3H); 13C NMR(101MHz,Chloroform-d)δ:151.19,149.25,147.97,144.16,140.84,137.39,137.02,130.63, 130.29,129.84,129.61,129.33,128.73,127.69,126.85,125.67,125.35,124.64,120.85,21.51.

[0069] Example 5

[0070] Synthesis of (E)-(5-chloro-1-tosylpent-1-en-2-yl)(phenyl)selane

[0071] The chemical structural formula is:

[0072]

[0073] Phenylseleno-p-toluenesulfonate (0.39 mmol), carbon nitride (0.17 mmol), 5-chloro-1-pentyne (0.20 mmol), and anhydrous DCM (1.0 mL) were added sequentially to a reaction flask under argon atmosphere. The reaction mixture was stirred at -20°C under blue LED illumination for 17 hours. The reaction mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was evaporated under reduced pressure and purified by chromatography to obtain the desired product as a white solid in 82% yield.

[0074] 1 H NMR(400MHz,Chloroform-d)δ:7.67(d,J=8.3Hz,2H),7.52(d,J=5.2Hz,2H),7.44(t,J=7.3Hz,1H),7.37(t,J=7.3Hz,2H) ,7.30(d,J=8.0Hz,2H),5.90(s,1H),3.59(t,J=6.5Hz,2H),3.00–2.93(m,2H),2.42(s,3H),2.11(dt,J=14.1,6.6Hz,2H); 13 C NMR (101MHz, Chloroform-d) δ: 159.07, 144.24, 139.31, 136.78, 130.28, 130.20, 129.99, 127.06, 125.81, 124.77, 44.21, 33.02, 30.92, 21.71.

[0075] Example 6

[0076] Synthesis of (E)-(1-(3-methoxyphenyl)-2-tosylvinyl)(phenyl)selane

[0077] The chemical structural formula is:

[0078]

[0079] Phenylseleno-p-toluenesulfonate (0.40 mmol), carbon nitride (0.16 mmol), 3-ethynylanisole (0.20 mmol), and anhydrous DCM (1.0 mL) were added sequentially to a reaction flask under argon atmosphere. The reaction mixture was stirred at -20°C under blue LED illumination for 25 h. The reaction mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was evaporated under reduced pressure and purified by chromatography to obtain the desired product as a white solid in a 92% yield.

[0080] 1 H NMR(400MHz,Chloroform-d)δ:7.60(d,J=7.2Hz,2H),7.42(dt,J=15.1,7.7Hz,3H),7.30(d,J=7.9Hz,2H),7.17(t,J=8.3Hz, 1H),7.09(d,J=7.9Hz,2H),6.84(d,J=8.5Hz,1H),6.79(d,J=7.6Hz,1H),6.61(s,1H),6.14(s,1H),3.73(s,3H),2.36(s,3H); 13 C NMR(101MHz,Chloroform-d)δ:159.00,156.89,143.63,138.86,136.74,135.85,130.32, 130.27,129.31,129.08,127.63,126.83,126.14,121.05,115.64,113.41,55.29,21.62.

[0081] Comparative Example 1

[0082] The difference between this comparative example and Example 2 is:

[0083] Phenylselenotoluenesulfonate (1.0 mmol), carbon nitride (0.16 mmol), propargyl acetate (0.20 mmol) and anhydrous DMSO (1.0 mL) were added sequentially into a reaction flask under an argon atmosphere.

[0084] Conclusion: The reaction product isomerized and the yield of the target product after purification is only 10%.

[0085] Comparative Example 2

[0086] The difference between this comparative example and Example 3 is:

[0087] Phenylseleno-p-toluenesulfonate (0.40 mmol), carbon nitride (3.0 mmol), 3-phenyl-1-propyne (0.20 mmol) and anhydrous DMSO (1.0 mL) were sequentially added into a reaction bottle under an argon atmosphere.

[0088] Conclusion: The yield of the target product after purification is only 67%.

[0089] Comparative Example 3

[0090] The difference between this comparative example and Example 3 is:

[0091] Phenylseleno-p-toluenesulfonate (1.0 mmol), carbon nitride (0.17 mmol), 3-phenyl-1-propyne (0.20 mmol) and anhydrous DMSO (1.0 mL) were sequentially added into a reaction bottle under an argon atmosphere.

[0092] Conclusion: The reaction product isomerized and the yield of the target product after purification is only 62%.

[0093] Obviously, the above embodiments are merely illustrative examples and are not intended to limit the embodiments. Those skilled in the art will readily appreciate that various variations, modifications, substitutions, variations, or alterations based on the above descriptions may be made. It is not necessary and impossible to enumerate all embodiments here. Obvious variations or alterations arising therefrom remain within the scope of protection of the present invention.

Claims

1. A method for synthesizing (E)-vinyl selenol sulfone compounds using an organic semiconductor g-C3N4 catalyst, characterized in that: The following steps are involved: Selenylsulfonate and alkyne are used as reaction substrates, graphite phase carbon nitride g-C3N4 is used as a catalyst, a free radical reaction occurs in an organic solvent and light conditions, and the (E)-vinyl selenolsulfone compound is obtained by filtration, recrystallization or chromatography purification; The chemical equation for the reaction is shown below: Wherein, the compound of formula (I) is selenosulfonate, R 1 is selected from naphthyl, benzofuranyl, pyridyl, thienyl, phenyl, phenyl substituted with one or more substituents selected from methyl, methoxy, phenoxy, halogen, cyano, nitro, trifluoromethyl, bromomethyl, acetamido or tert-butyl; R 2 selected from naphthyl, indenyl, pyridyl, thienyl, benzyl, phenethyl, phenylpropyl, phenylbutyl, phenylpentyl, phenyl, phenyl substituted with one or more substituents selected from methoxy, ethoxy, phenoxy, trifluoromethoxy, hydroxy, halogen, cyano, nitro, trifluoromethyl, aldehyde, methyl, ethyl, isopropyl or tert-butyl; The compound of formula (II) is an alkyne, R 3 Selected from C1~C 16 a linear or branched alkyl group, a C3-C6 cycloalkyl group, a cyclohexenyl group, a chloromethyl group, a chloroethyl group, a chloropropyl group, a chlorobutyl group, an ethyl ketone group, a dimethylaminomethyl group, a cyano group, a naphthyl group, a pyridyl group, a pyrrolyl group, a quinolyl group, a thienyl group, a methyl acetate group, a methyl benzoate group, a benzoic acid group, a methoxymethyl group, a phenoxymethyl group, a p-methylphenoxymethyl group, a benzyloxyethyl group, a benzyloxypropyl group, a benzyl group, a phenethyl group, a phenyl group, or a phenyl group substituted with one or more substituents selected from the group consisting of a methoxy group, a trifluoromethoxy group, a methyl formate group, an ethynyl group, a halogen group, a cyano group, a nitro group, a trifluoromethyl group, a trifluoromethoxy group, an aldehyde group, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

2. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 1, characterized in that: The organic solvent is selected from at least one of dimethyl sulfoxide, dichloromethane, ethyl acetate, acetonitrile, dimethylformamide, tetrahydrofuran, n-hexane, 1,4-dioxane, diethyl ether, and carbon tetrachloride.

3. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 1, characterized in that: The lighting condition is sunlight, fluorescent light, white LED light or blue LED light.

4. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 3, characterized in that: The mixture is stirred under the aforementioned light conditions for a period of 1 hour to 20 days.

5. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 1, characterized in that: The reaction temperature is -78°C to 100°C.

6. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 5, characterized in that: The reaction temperature is room temperature or -20°C.

7. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 1, characterized in that: The molar ratio of the alkyne to the selenosulfonate is 1:(0.2-4.0).

8. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 1, characterized in that: The molar ratio of the alkyne to the g-C3N4 is 1:(0.4-2.0).

9. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 1, characterized in that: The preparation method of g-C3N4 is as follows: (1) adding urea to a crucible with a lid, covering the crucible with the lid, heating the crucible for 3.5-4.5 hours to 540-560°C to obtain a yellow solid, and cooling the crucible to room temperature; (2) further heating the yellow solid in an open crucible for 1.5-2.5 hours to 490-510°C to obtain g-C3N4.

10. The method for synthesizing (E)-vinyl selenol sulfone compounds catalyzed by the organic semiconductor g-C3N4 according to claim 9, characterized in that: The heating rate of the heating reaction in step (1) is 2.5°C / min; the heating rate of the further heating reaction in step (2) is 5°C / min.

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