阅读说明：本技术 一种可见光促进β-羟基硒醚化合物的合成方法 (Synthesis method of visible light-promoted beta-hydroxyselenide compound ) 是由 刘功清 凌勇 易伟 王鹏飞 周晨凡 张云倩 于 2020-12-28 设计创作，主要内容包括：本发明涉及有机合成化学技术领域,具体为一种可见光促进β-羟基硒醚化合物的合成方法,包括以下步骤：A、在反应器中依次加入化合物1和化合物2；B、敞口条件下,在一定温度条件下和光源照射下将上述化合物1和化合物2进行搅拌反应；C、反应结束后减压蒸除溶剂得粗产物；D、经柱层析提纯得到β-羟基硒醚化合物3。本发明以烯烃和二硒醚为原料,以乙腈/水混合溶剂,丙酮/水混合溶剂中的一种为溶剂,反应温度为室温,白色荧光的光源照射下,高效合成出β-羟基硒醚化合物；该方法与传统的合成方法相比,具有反应条件温和,在室温下可顺利进行；操作简单,所有操作均可在敞开体系中进行；原料易得,收率高,官能团兼容性好,底物适用范围广。(The invention relates to the technical field of organic synthetic chemistry, in particular to a method for synthesizing a visible light-promoted beta-hydroxyselenide compound, which comprises the following steps: A. sequentially adding a compound 1 and a compound 2 into a reactor; B. under the open condition, the compound 1 and the compound 2 are stirred and react under the condition of certain temperature and the irradiation of a light source; C. after the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product; D. purifying by column chromatography to obtain beta-hydroxyselenide compound 3. The beta-hydroxyselenide compound is efficiently synthesized by taking olefin and diselenide as raw materials, taking one of acetonitrile/water mixed solvent and acetone/water mixed solvent as a solvent, and irradiating the raw materials by a white fluorescent light source at room temperature; 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 operation is simple, and all the operations can be carried out in an open system; the raw materials are easy to obtain, the yield is high, the functional group compatibility is good, and the application range of the substrate is wide.)

1. A method for synthesizing a visible light-promoted beta-hydroxyselenide compound is characterized by comprising the following steps: the method comprises the following steps:

A. sequentially adding a compound 1 and a compound 2 into a reactor;

B. under the open condition, the compound 1 and the compound 2 are stirred and react under the condition of certain temperature and the irradiation of a light source;

C. after the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product;

D. purifying by column chromatography to obtain beta-hydroxyselenide compound 3.

2. The method for synthesizing a visible light-promoted β -hydroxyselenide compound according to claim 1, wherein: in the step (A), the reactor is a round-bottom flask, and the beta-hydroxyselenide compound is prepared through a chemical reaction, wherein the reaction equation is as follows:

wherein compound 1 can be styrene, each substituted styrene, or represent each optionally substituted mono-or bicyclic heteroaryl ethylene having 5 to 10 ring atoms, as well as various classes of aliphatic olefins; the compound 2 adopts diaryl diselenide or dialkyl diselenide.

3. The method for synthesizing a visible light-promoted β -hydroxyselenide compound according to claim 1, wherein: in the step (A), the molar ratio of the compound 1 to the compound 2 is 1: 0.5.

4. The method for synthesizing a visible light-promoted β -hydroxyselenide compound according to claim 1, wherein: in the step (B), the reaction is carried out under the open condition and the room temperature condition, and the white light emitted by a compact fluorescent lamp with 23 watts is adopted for the room temperature reaction.

5. The method for synthesizing a visible light-promoted β -hydroxyselenide compound according to claim 1, wherein: in the step (C), the solvent is one of a mixed solvent of acetonitrile and water or a mixed solvent of acetone and water.

6. The method for synthesizing a visible light-promoted β -hydroxyselenide compound according to claim 1, wherein: in the step (D), the eluent used for column chromatography purification is a mixed solvent of petroleum ether and ethyl acetate, wherein the petroleum ether: the volume ratio of ethyl acetate is (1-30): 1.

Technical Field

The invention relates to the technical field of organic synthetic chemistry, in particular to a method for synthesizing a visible light-promoted beta-hydroxyselenide compound.

Background

Selenium is an essential trace element of the human body, which is closely related to human health ((a) Nogueira, c. w.; Zeni, g.; Rocha, j.b.t., chem.rev.2004,104, 6255-6286; (b) Derek, w.j.; Risto, l., Selenium and Tellurium Chemistry: From Small Molecules to biomasses and materials, spring-Verlag: Berlin, 2011.). A large number of researches show that the organic selenium compound has pharmacological effects of resisting virus, tumors, inflammation and aging, preventing and treating cardiovascular diseases and the like. Such as Ebselen (Ebselen) and Selenazofurn. ((a) Klayman, D.L.; Gunther, W.H.H.organic Selenium Compounds: thermal Chemistry and Biology; John Wiley & Sons, New York, 1973; b) Nogueira, C.W.; Zeni, G.G.; Rocha, J.B.T.Chem.Rev. 2004,104, 6255-.

Beta-hydroxyselenoether compounds are an important class of organic synthetic intermediates ((a) Rigby, J.H.; Maharof, U.S.M.; Mateo, M.E., J.Am.chem.Soc.2000,122, 6624-6628; (b) Azuma, H.; Tamagaki, S.; Ogino, K.; J.Org.chem.2000,65, 3538-. The beta-hydroxyselenoethers can be converted to alpha, beta-unsaturated ketones or alcohols, epoxides, oxazolidinones, aminoalcohols, olefins, and oxygen-containing heterocyclic compounds by oxidative elimination. The traditional method for synthesizing beta-hydroxyselenide is generally obtained by ring-opening reaction of an epoxy compound by selenium negative ions ((a) Yang, M.; Zhu, C.; Yuan, F.; Huang Y.; PanY.; Org.Lett.2005,7, 1927-. These methods usually require expensive raw materials (for example, selenium metal such as Se-Sn, Se-Na and Se-Yb, which are difficult to commercialize and unstable reagents, are used for activation to prepare selenium negative ions), or require harsh reaction conditions, and have low conversion efficiency and a large amount of byproducts, and the methods also suffer from a problem that the substrate range is not wide enough.

Olefin is a large amount of chemicals which are simple and easy to obtain, and the double functionalization reaction of olefin can quickly construct complex molecules and has wide application in organic synthesis. Visible light is a clean and pollution-free energy source, and in recent years, organic synthesis reaction promoted by visible light is greatly developed. However, literature studies have shown that synthetic methods for the preparation of organoselenium compounds based on visible light-promoted olefin functionalization are in the infancy and in limited literature reports usually require the addition of certain amounts of expensive photocatalysts. The visible light-promoted bifunctional strategy for olefins allows the rapid synthesis of complex molecules from simple, readily available olefin feedstocks. However, the method for synthesizing the beta-hydroxyselenide compound by visible light acceleration based on olefin without using a photocatalyst is not reported, and the need for continuous research and exploration still exists, which is the basis and the motivation for completing the invention.

Disclosure of Invention

The invention aims to provide a method for synthesizing a visible light-promoted beta-hydroxyselenide compound, so as to solve the problems in the background technology.

In order to achieve the purpose, the invention provides the following technical scheme: a method for synthesizing a visible light-promoted beta-hydroxyselenide compound comprises the following steps:

A. sequentially adding a compound 1 and a compound 2 into a reactor;

B. under the open condition, the compound 1 and the compound 2 are stirred and react under the condition of certain temperature and the irradiation of a light source;

C. after the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product;

D. purifying by column chromatography to obtain beta-hydroxyselenide compound 3.

Preferably, in the step (a), the reactor is a round-bottom flask, and the β -hydroxyselenide compound is prepared by a chemical reaction, wherein the reaction equation is as follows:

wherein compound 1 can be styrene, each substituted styrene, or represent each optionally substituted mono-or bicyclic heteroaryl ethylene having 5 to 10 ring atoms, as well as various classes of aliphatic olefins; the compound 2 adopts diaryl diselenide or dialkyl diselenide.

Preferably, in the step (A), the molar ratio of the compound 1 to the compound 2 is 1: 0.5.

Preferably, in the step (B), the reaction is carried out under open conditions and under room temperature conditions, and the room temperature reaction is carried out by irradiating white light emitted by a compact fluorescent lamp with 23 watts.

Preferably, in the step (C), the solvent is one of a mixed solvent of acetonitrile and water or a mixed solvent of acetone and water.

Preferably, in the step (D), the eluent used for column chromatography purification is a mixed solvent of petroleum ether and ethyl acetate, wherein the ratio of petroleum ether: the volume ratio of ethyl acetate is (1-30): 1.

compared with the prior art, the invention has the beneficial effects that: the invention provides a synthesis method of a visible light promoted beta-hydroxyselenide compound, which comprises the steps of taking olefin and diselenide as raw materials, taking one of acetonitrile/water mixed solvent and acetone/water mixed solvent as a solvent, and efficiently synthesizing the beta-hydroxyselenide compound under the irradiation of a white fluorescent light source at room temperature; 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 operation is simple, and all the operations can be carried out in an open system; the raw materials are easy to obtain, the yield is high, the compatibility of functional groups is good, and the application range of a substrate is wide; meanwhile, the method avoids using expensive transition metal catalyst, and has the characteristics of economy, environmental protection and the like.

Drawings

FIG. 1 is a hydrogen spectrum of the product obtained in example 1 of the present invention;

FIG. 2 is a carbon spectrum of the product obtained in example 1 of the present invention;

FIG. 3 is a hydrogen spectrum of the product obtained in example 2 of the present invention;

FIG. 4 is a carbon spectrum of the product obtained in example 2 of the present invention;

FIG. 5 is a hydrogen spectrum of the product obtained in example 3 of the present invention;

FIG. 6 is a carbon spectrum of the product obtained in example 3 of the present invention;

FIG. 7 is a hydrogen spectrum of the product obtained in example 4 of the present invention;

FIG. 8 is a carbon spectrum of the product obtained in example 4 of the present invention;

FIG. 9 is a hydrogen spectrum of the product obtained in example 5 of the present invention;

FIG. 10 is a carbon spectrum of the product obtained in example 5 of the present invention;

FIG. 11 is a hydrogen spectrum of the product obtained in example 6 of the present invention;

FIG. 12 is a carbon spectrum of the product obtained in example 6 of the present invention;

FIG. 13 is a hydrogen spectrum of the product obtained in example 7 of the present invention;

FIG. 14 is a carbon spectrum of the product obtained in example 7 of the present invention;

FIG. 15 is a hydrogen spectrum of the product obtained in example 8 of the present invention;

FIG. 16 is a carbon spectrum of the product obtained in example 8 of the present invention;

FIG. 17 is a hydrogen spectrum of the product obtained in example 9 of the present invention;

FIG. 18 is a carbon spectrum of the product obtained in example 9 of the present invention;

FIG. 19 is a hydrogen spectrum of the product obtained in example 10 of the present invention;

FIG. 20 is a carbon spectrum of the product obtained in example 10 of the present invention.

Detailed Description

The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the 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.

Referring to fig. 1-20, the present invention provides a technical solution: a method for synthesizing a visible light-promoted beta-hydroxyselenide compound comprises the following steps:

A. sequentially adding a compound 1 and a compound 2 into a reactor;

B. under the open condition, the compound 1 and the compound 2 are stirred and react under the condition of certain temperature and the irradiation of a light source;

C. after the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product;

D. purifying by column chromatography to obtain beta-hydroxyselenide compound 3.

A method for purifying olefin by using olefin 1 as a raw material, using selenide 2 as diaryl diselenide and dialkyl diselenide, charging 10.5 mmol of olefin and 20.25 mmol of diselenide into a 10ml round-bottom flask containing 2.0-3.0 ml of one of acetonitrile/water mixed solvent and acetone/water mixed solvent at room temperature, after the addition is finished, placing a 23W white compact fluorescent lamp at a position 1 cm away from a reaction tube, reacting at room temperature for 20 hours under an open condition, pouring reaction liquid into water, extracting by using ethyl acetate, drying an organic layer by using anhydrous sodium sulfate, filtering, removing the solvent by a rotary evaporator, purifying residues by using a silica gel column, wherein the specification of the silica gel is 200-300 meshes, and eluent used for column chromatography purification is a mixed solvent of petroleum ether and ethyl acetate, petroleum ether: the volume ratio of ethyl acetate is (1-30): 1 to obtain the target product beta-hydroxy selenide, and the yield is between 90 and 99 percent according to different reactions.

Example 1

Charging styrene (0.5 mmol), diphenyl diselenide (0.25 mmol) and a mixed solvent of acetonitrile/water (1/1, 2 mL) into a 10mL round bottom flask equipped with a magnetic stirrer at room temperature, placing a 23W white compact fluorescent lamp at a position 1 cm away from the round bottom flask, reacting at open room temperature for 20 hours, pouring the reaction solution into 10mL of water after the reaction is finished, extracting three times with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, filtering, removing the solvent from the organic layers through a rotary evaporator, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 10:1) to obtain 126 mg of colorless oily liquid with the yield of 91%,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝7.8–7.45 (m,2H),7.26–7.23(m,4H),7.23–7.16(m,4H),4.66(dd,J＝9.4,3.7Hz,1H), 3.22(dd,J＝12.8,3.7Hz,1H),3.06(dd,J＝12.8,9.4Hz,1H),2.75(brs,3H). ¹³C NMR(100MHz,CDCl₃)δ/ppm＝141.4,132.1,128.2,128.1,127.5,126.9, 126.4,124.76,71.2,37.4.

example 2

Charging 4-tert-butylstyrene (0.5 mmol), diphenyl diselenide (0.25 mmol) and a mixed solvent of acetonitrile/water (1/1, 2 mL) into a 10mL round-bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 1 cm from the round-bottom flask, reacting at room temperature under an open condition for 20 hours, pouring the reaction solution into 10mL of water after the reaction is completed, extracting three times with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, filtering, removing the solvent from the organic layer through a rotary evaporator, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 15:1) to obtain 160 mg of colorless oily liquid with the yield of 96%,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝7.60–7.44 (m,2H),7.26(d,J＝8.6Hz,2H),7.24–7.14(m,3H),6.97(d,J＝8.5Hz,2H), 4.76–4.58(m,1H),3.19(dd,J＝12.8,3.7Hz,1H),3.02(dd,J＝12.8,9.5Hz, 1H),2.85(brs,1H),2.21(s,3H).¹³C NMR(100MHz,CDCl₃)δ/ppm＝168.5, 149.1,139.0,132.1,128.3,128.0,126.4,125.9,120.6,70.7,37.4,20.1.

example 3

Charging 4-methylstyrene (0.5 mmol), diphenyldiselenide (0.25 mmol) and a mixed solvent of acetonitrile/water (1/1, 2 mL) into a 10mL round-bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 1 cm from the round-bottom flask, reacting at room temperature under an open atmosphere for 20 hours, pouring the reaction solution into 10mL of water after the reaction is completed, extracting three times with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, filtering, removing the solvent from the organic layer by a rotary evaporator, purifying the residue with a silica gel column (the silica gel specification is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 20:1) to obtain 135 mg of colorless oily liquid with a yield of 93%,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝7.46– 7.44(m,2H),7.23–7.17(m,3H),7.16–7.10(m,2H),7.05(d,J＝7.7Hz,2H), 4.63(dd,J＝9.2,2.9Hz,1H),3.19(dd,J＝12.7,3.9Hz,1H),3.05(dd,J＝12.7, 9.2,Hz,1H),2.76(dt,J＝13.3,2.9Hz,1H),2.25(s,3H).¹³C NMR(100MHz, CDCl₃)δ/ppm＝138.5,136.6,132.0,128.2,128.15,128.13,126.3,124.7,71.0, 37.3,20.1.

example 4

Charging 4-chlorostyrene (0.5 mmol), diphenyl diselenide (0.25 mmol) and a mixed solvent of acetonitrile/water (1/1, 2 mL) into a 10mL round-bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 1 cm from the round-bottom flask after the addition, reacting at room temperature for 20 hours under an open condition, pouring the reaction solution into 10mL of water after the reaction is completed, extracting three times with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, filtering, removing the solvent from the organic layers through a rotary evaporator, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 15:1) to obtain 140 mg of colorless oily liquid with the yield of 90%,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝7.65– 7.29(m,2H),7.30–7.00(m,7H),4.60(dt,J＝9.2,3.1Hz,1H),3.16(dd,J＝ 12.8,3.8Hz,1H),2.98(dd,J＝12.8,9.3Hz,1H),2.88(d,J＝2.7Hz,1H).¹³C NMR(100MHz,CDCl₃)δ/ppm＝139.9,132.5,132.2,128.3,127.8,127.6,126.5, 126.2,70.4,37.3.

example 5

Charging 4-methyl-5-vinyl thiazole (0.5 mmol), diphenyl diselenide (0.25 mmol) and a mixed solvent of acetonitrile/water (1/1, 2 mL) into a 10mL round-bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a position 1 cm away from the round-bottom flask to react for 20 hours under an open condition, pouring the reaction solution into 10mL water after the reaction is finished, extracting three times with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, filtering, removing the solvent from the organic layers through a rotary evaporator, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 2:1) to obtain 140 mg of colorless oily liquid with the yield of 94%,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃):δ/ppm＝8.76(s, 1H),7.50–7.41(m,2H),7.25–7.17(m,3H),3.92(s,2H),2.66(s,3H).¹³C NMR(100MHz,CDCl₃):δ/ppm＝187.1,133.2,130.5,128.3,128.2,127.4,127.2, 126.7,35.7,17.2.

example 6

At room temperature, a 10mL round bottom flask with a magnetic stirrer is filled with 2-vinylferrocene (0.5 mmol), diphenyl diselenide (0.25 mmol) and a mixed solvent of acetonitrile/water (1/1, 2 mL), after the addition, a 23-watt white compact fluorescent lamp is placed at a position 1 cm away from the round bottom flask and is reacted for 20 hours under an open condition at room temperature, after the reaction is completed, the reaction liquid is poured into 10mL of water, extracted with ethyl acetate for three times, organic layers are combined and dried by anhydrous sodium sulfate, filtered, the organic layer is passed through a rotary evaporator to remove the solvent, the residue is purified by a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 10:1) to obtain 173 mg of colorless oily liquid with the yield of 90 percent,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝7.50–7.45 (m,2H),7.24–7.16(m,3H),4.51–4.39(m,1H),4.22–4.19(m,1H),4.12(q,J ＝1.8Hz,1H),4.10(s,7H),3.18(dd,J＝12.5,4.2Hz,1H),3.09(dd,J＝12.5,8.5 Hz,1H),2.46(d,J＝3.2Hz,1H).¹³C NMR(100MHz,CDCl₃)δ/ppm＝131.8, 128.9,128.1,126.1,90.6,67.6,67.4,67.1,67.0,66.0,64.6,35.7.

example 7

At room temperature, a 10mL round bottom flask with a magnetic stirrer is filled with cyclohexene (0.5 mmol), diphenyl diselenide (0.25 mmol), a mixed solvent of acetonitrile/water (1/1, 2 mL), after the addition, a 23-watt white compact fluorescent lamp is placed at a position 1 cm away from the round bottom flask and is reacted for 20 hours under an open condition at room temperature, after the reaction is completed, the reaction liquid is poured into 10mL of water, extracted with ethyl acetate for three times, organic layers are combined, dried by anhydrous sodium sulfate, filtered, the organic layer is subjected to solvent removal by a rotary evaporator, the residue is purified by a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 25:1) to obtain 124 mg of colorless oily liquid with the yield of 97 percent,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝7.60– 7.43(m,2H),7.31–7.12(m,3H),3.25(tdd,J＝10.3,4.3,1.4Hz,1H),2.90(s, 1H),2.82(ddd,J＝12.3,10.0,4.0Hz,1H),2.23–1.96(m,1H),1.67–1.62(m, 1H),1.58–1.52(m,1H),1.44–1.02(m,5H).¹³C NMR(100MHz,CDCl₃) δ/ppm＝135.1,128.0,127.1,125.5,71.2,52.5,32.8,32.3,25.8,23.4.

example 8

A10-mL round-bottom flask equipped with a magnetic stirrer was charged at room temperature with 2, 3-dimethyl-2-butene (0.5 mmol), diphenyldiselenide (0.25 mmol), and a mixed solvent of acetonitrile/water (1/1, 2 mL), after which a 23-watt white compact fluorescent lamp was placed at a distance of 1 cm from the round-bottom flask and allowed to react at room temperature for 20 hours under open conditions, after completion of the reaction, the reaction solution was poured into 10mL of water, extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, the organic layer was freed of the solvent by a rotary evaporator, and the residue was purified with a silica gel column (200-300 mesh size silica gel, eluent petroleum ether/ethyl acetate 20:1) to give 118 mg of colorless oily liquid at a yield of 92%, example 9

Charging styrene (0.5 mmol), dimethyl diselenide (0.25 mmol), acetonitrile/water mixed solvent (1/1, 2 mL) into a 10mL round bottom flask equipped with a magnetic stirrer at room temperature, placing a 23W white compact fluorescent lamp at a position 1 cm away from the round bottom flask, reacting at open room temperature for 20 hours, pouring the reaction solution into 10mL water after the reaction is completed, extracting three times with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, filtering, removing the solvent from the organic layers through a rotary evaporator, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate ═ 18:1) to obtain 99 mg of colorless oily liquid with the yield of 92%,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝8.01– 6.80(m,5H),4.67(ddd,J＝9.1,4.1,2.5Hz,1H),2.97(s,1H),2.83(dd,J＝12.8, 4.2Hz,1H),2.72(dd,J＝12.8,9.0Hz,1H),1.87(s,3H).¹³C NMR(100MHz, CDCl₃)δ/ppm＝141.7,127.5,126.8,124.8,71.0,34.9,3.6.

example 10

After charging styrene (0.5 mmol), dibenzyldiselenide (0.25 mmol), and a mixed solvent of acetonitrile/water (1/1, 2 mL) into a 10mL round-bottomed flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 1 cm from the round-bottomed flask, reacting at open room temperature for 20 hours, pouring the reaction solution into 10mL of water after completion of the reaction, extracting three times with ethyl acetate, combining the organic layers, drying with anhydrous sodium sulfate, filtering, removing the solvent from the organic layer by means of a rotary evaporator, purifying the residue with a silica gel column (200-300 mesh size, petroleum ether/ethyl acetate 14:1 as eluent) to obtain 137 mg of a white solid with a yield of 94%,

the nuclear magnetic spectrum data of the obtained product are as follows:¹H NMR(400MHz,CDCl₃)δ/ppm＝7.45– 7.02(m,10H),4.55(dt,J＝8.7,3.4Hz,1H),3.65(s,2H),2.79–2.72(m,2H), 2.67(dd,J＝13.1,8.8Hz,1H).¹³C NMR(100MHz,CDCl₃)δ/ppm＝141.8,137.8, 127.9,127.6,127.4,126.8,125.9,124.7,71.3,33.1,26.4.

in summary, the synthesis method of the visible light promoted beta-hydroxyselenide compound provided by the invention uses olefin and diselenide as raw materials, uses one of acetonitrile/water mixed solvent and acetone/water mixed solvent as a solvent, and efficiently synthesizes the beta-hydroxyselenide compound under the irradiation of a white fluorescent light source at room temperature; 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 operation is simple, and all the operations can be carried out in an open system; the raw materials are easy to obtain, the yield is high, the compatibility of functional groups is good, and the application range of a substrate is wide; meanwhile, the method avoids using expensive transition metal catalyst, and has the characteristics of economy, environmental protection and the like.

The invention is not described in detail, but is well known to those skilled in the art.

It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.