A method for electrochemically promoting synthesis of selenophenyl substituted alkyne derivatives
The acetylene difunctionalization reaction was achieved by electrochemical methods at room temperature and pressure, which solved the problems of complicated steps and harsh conditions in the existing acetylene difunctionalization reaction. A series of selenium phenyl alkyne derivatives were synthesized, which have the advantages of being environmentally friendly and easy to operate.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- GUILIN UNIVERSITY OF TECHNOLOGY
- Filing Date
- 2026-04-01
- Publication Date
- 2026-06-23
AI Technical Summary
In the prior art, the 1,2-bifunctional/alkynylation reaction of acetylene depends on multi-step alkaline conditions, which has problems such as low step economy, harsh reaction conditions and poor functional group compatibility. Moreover, green 1,2-bifunctional/alkynylation reaction has not been studied.
An electrochemical method was employed, using acetylene and diselenyl ether derivatives as starting materials, tetrabutylammonium iodide as the electrolyte, dimethyl sulfoxide as the solvent, a graphite rod as the anode, and a platinum sheet as the cathode, to achieve the alkynylation difunctionalization reaction of acetylene at room temperature and pressure, avoiding the use of metal catalysts and additional oxidants.
A series of selenylphenyl alkyne derivatives were successfully synthesized under mild conditions, simplifying the operation process, improving the practicality and environmental friendliness of the synthesis strategy, and achieving effective fixation of acetylene.
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Abstract
Description
Technical Field
[0001] This invention belongs to the field of organic synthetic chemistry, specifically relating to an electrochemically promoted method for the synthesis of selenium phenyl-substituted alkyne derivatives. Background Technology
[0002] Alkynes, as an important class of organic compounds, occupy a pivotal position in the fields of organic synthesis and materials science due to their unique reactivity and linear geometry. Chemical reviews ,2015, 115(17): 9028-9072; Chemical Reviews ,2016, 116(10): 5894-5986.). They are not only key precursors for constructing a variety of complex organic molecules, but also have wide applications in the synthesis of pharmaceuticals, agrochemicals and functional materials. Chemical Reviews ,2021, 121(12): 6744-6776; Chemical Society Reviews ,2016, 45(8): 2212-2238.). With the advancement of science and technology and the growth of demand, the efficient and selective functionalization of alkynes has become one of the hot topics in chemical research. Among them, the bifunctionalization reaction has attracted much attention because it can introduce two functional groups at once. Nature Reviews Chemistry ,2023, 7(6): 405-423; Angewandte Chemie International Edition ,2019, 58(34): 11704-11708.).
[0003] In the research background of alkyne difunctionalization reactions, significant progress has been made in the difunctionalization reactions of substituted alkynes. Nature communications ,2018, 9(1): 4543; Nature Catalysis ,2019, 2(6):529-536.). These types of reactions typically rely on metal-catalyzed strategies, enabling highly selective functionalization under mild conditions, providing a powerful tool for synthesizing organic molecules with specific structures and functions. However, although research on substituted alkynes is quite mature, research on the bifunctionalization reactions of acetylene, as the simplest alkyne, is relatively lagging behind. Chemical reviews ,2014, 114(3): 1761-1782; ACS Catalysis ,2023, 13(4): 2422-2431.), and in known reports of acetylene difunctionalization, acetylene is usually used as an alkenyl or alkyl source, and 1,2-difunctional / alkynylation reactions using acetylene as an alkynyl source have not been reported (except for base-promoted multi-step synthetic methods).
[0004] Currently, acetylene-based 1,2-bifunctional / alkynylation reactions heavily rely on multi-step synthetic strategies under basic conditions, requiring four separate reaction steps: strong base removal of one end of the acetylene → reaction with an electrophile → strong base secondary hydrogen removal → reaction with another electrophile molecule. This approach suffers from drawbacks such as low step economy and atom economy, harsh reaction conditions, and poor functional group compatibility. Angewandte Chemie International Edition ,2018, 57(33),10718-10722.). Green 1,2-bifunctional / alkynylation based on acetylene has not yet been studied.
[0005] In light of this, our research group has long been engaged in the study of 1,2-bifunctional / alkynylation reactions of acetylene. We have achieved a highly efficient alkynylation bifunctionalization reaction of acetylene with diselenyl ether derivatives under electrochemical conditions. This breakthrough opens a novel pathway for the synthesis of selenylphenyl-substituted alkyne derivatives. It is worth emphasizing that this method eliminates the dependence on metal catalysts or additional oxidants. Furthermore, this synthetic strategy demonstrates unique environmental advantages, with a simple and rapid operation process, and can effectively fix acetylene gas under ambient temperature and pressure conditions. Summary of the Invention
[0006] This invention aims to achieve the green bifunctionalization reaction of acetylene through an innovative electrochemically promoted strategy, thereby constructing a rich variety of selenylphenyl alkyne derivatives.
[0007] The present invention utilizes acetylene and diselenyl ether derivatives as starting materials, tetrabutylammonium iodide as the electrolyte, dimethyl sulfoxide as the solvent, a graphite rod as the anode, and a platinum sheet as the cathode. The reaction is carried out under stirring at a current of 6 mA to construct selenylphenyl ynylated derivatives in one step. This strategy eliminates the need for metal catalysts or additional oxidants, and successfully synthesizes selenylphenyl ynylated derivatives at room temperature. Furthermore, this synthetic strategy is not only environmentally friendly but also simple to operate, achieving effective acetylene fixation under normal pressure, significantly enhancing its practicality.
[0008] The objective of this invention is achieved through the following technical solution.
[0009] An electrochemically promoted synthesis method for selenylphenyl-substituted alkyne derivatives includes the following steps: In an unseparated electrolytic cell, a diselenyl ether derivative, electrolyte, and solvent are added, and an anode and cathode are inserted. An acetylene balloon is then connected to the reaction system, and the reaction is carried out at room temperature for 7 hours. After the reaction, the crude product is obtained by rotary evaporation under reduced pressure. Finally, the selenylphenyl-substituted alkyne derivative is purified by column chromatography. Furthermore, the chemical reaction equation for preparing selenylphenyl-substituted alkynylated derivatives is shown below:
[0010] In the formula, R is selected from one of phenyl, 4-fluorophenyl, 4-methylphenyl, 2,4,6-trimethylphenyl, 4-tert-butylphenyl, 2-methylphenyl, 2-fluorophenyl, 3-nitrophenyl, 3-methylphenyl and benzyl.
[0011] Furthermore, the electrolyte is selected from one of tetrabutylammonium iodide, tetrabutylammonium tetrafluoroborate, tetrabutylammonium thiocyanate and tetrabutylammonium perchlorate, preferably tetrabutylammonium iodide.
[0012] Furthermore, the solvent is selected from one of dimethyl sulfoxide, 1,2-dichloroethane, dichloromethane, acetonitrile, tetrahydrofuran, and ethanol, preferably dimethyl sulfoxide.
[0013] Furthermore, the anode electrode material is one of graphite rod and stainless steel sheet (SS), preferably graphite rod.
[0014] Furthermore, the cathode electrode material is one of stainless steel sheet (SS), platinum sheet, nickel sheet, and graphite rod, preferably platinum sheet.
[0015] Furthermore, the molar ratio of the diselenyl ether compound to the electrolyte is 1:1 to 2, preferably 1:2.
[0016] Furthermore, the electrolysis current is 6-10 mA, preferably 6 mA.
[0017] Furthermore, the separation method for the crude selenylphenyl-substituted alkyne derivative is column chromatography. Petroleum ether and ethyl acetate are used as eluents in the column chromatography, with a volume ratio of petroleum ether:ethyl acetate = 1~100:1, preferably 100:1.
[0018] The principle of this invention is as follows: First, the iodide anion of tetrabutylammonium iodide (TBAI) is anoly oxidized to generate an iodine radical. Subsequently, the iodine radical undergoes a single-electron transfer with diselenyl ether to generate a diselenyl ether radical cation. This intermediate is unstable and immediately decomposes to generate a selenophenyl cation and a selenophenyl radical. The selenophenyl radical captures acetylene to generate an alkenyl radical intermediate. This radical intermediate is then anoly oxidized to generate a selenoium ion. Immediately afterwards, the selenoium ion and the iodide anion combine to form an alkenyliodine intermediate, which loses hydrogen iodide to generate a terminal alkyne intermediate. This intermediate undergoes the same process to form the final target product.
[0019] Compared with the prior art, the present invention has the following advantages and beneficial effects: (1) This invention realizes the 1,2-bifunctional / alkynylation reaction of acetylene under electrochemical conditions, and successfully synthesizes a series of selenylphenyl alkynylated derivatives that were previously difficult to prepare. It is worth noting that there are very few reports on electrochemically promoted bifunctionalization reactions of acetylene, and no reports have been found on green alkynylation reactions of acetylene.
[0020] (2) This invention uses acetylene as the alkynyl C2 synthon and successfully achieves the bifunctionalization reaction of acetylene under mild conditions. This synthetic method is significantly different from existing technologies. This strategy avoids the use of metal catalysts and equivalent toxic oxidants, and the synthesis of selenylphenyl alkynylation derivatives can be successfully achieved at room temperature. In addition, this synthetic strategy is simple to operate and can achieve effective fixation of acetylene under normal pressure, which significantly improves the practicality of this synthetic strategy. Attached Figure Description
[0021] Figure 1 , Figure 2 These are the proton and carbon spectra of the target product obtained in Example 1; Figure 3 , Figure 4 These are the proton and carbon spectra of the target product obtained in Example 2; Figure 5 , Figure 6 These are the proton and carbon spectra of the target product obtained in Example 3; Figure 7 This is a crystal structure diagram of the target product obtained in Example 3; Figure 8 , Figure 9 These are the proton and carbon spectra of the target product obtained in Example 4. Detailed Implementation
[0022] The present invention will be further described below through specific embodiments, but the scope of protection and implementation of the present invention are not limited thereto.
[0023] Example 1 In a three-necked flask equipped with a stirrer, 0.1 mmol of diphenyldiselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. Using a graphite rod as the anode and a platinum sheet as the cathode, an acetylene balloon was connected to the reaction apparatus. The reaction was carried out under stirring at 6 mA at room temperature for 7 hours. After the reaction was completed, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The organic phases were combined, and the crude product was obtained by rotary evaporation under reduced pressure. Finally, the crude product was purified by column chromatography to obtain the final product, 1,2-bis(phenylselenoyl)acetylene, in 86% yield.
[0024] The proton and carbon spectra of the obtained target product are as follows: Figure 1 and Figure 2 As shown, the structural characterization data is as follows: 1 H NMR (500 MHz, Chloroform- d ) d = 7.21 – 7.24 (d, J = 7.34, 1H), 7.28 –7.32 (d,J = 7.21, 2H), 7.50 – 7.52 (d, J = 7.76, 2H). 13 C NMR (126 MHz, Chloroform- d ) d = 84.69, 127.17, 128.68, 129.29,129.54.HRMScalcd for C 14 H 10 Se2Na + [M+Na] + : 360.9011; found 360.9010. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0025] Example 2 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(4-fluorophenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. Using a graphite rod as the anode and a platinum sheet as the cathode, an acetylene balloon was connected to the reaction apparatus. The reaction was carried out under stirring at 6 mA at room temperature for 7 hours. After the reaction was completed, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The combined organic phases and the crude product obtained by rotary evaporation under reduced pressure were then purified by column chromatography to obtain the final product 1,2-bis((4-fluorophenyl)seleno)acetylene in 56% yield.
[0026] The proton and carbon spectra of the obtained target product are as follows: Figure 3 and Figure 4 As shown, the structural characterization data is as follows: 1 H NMR (500 MHz, Chloroform- d ) d = 7.02 – 7.08 (t, J = 8.66, 4H), 7.48 –7.54 (dd, J = 5.14, 8.76, 4H). 13 C NMR (126 MHz, Chloroform- d ) d = 84.71, 116.71, 116.88, 123.40,123.43, 131.11, 131.17, 161.43, 163.39.HRMScalcd for C14 H8F2Se2Na + [M+Na] + :396.8822; found 396.8815. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0027] Example 3 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(4-methylphenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. An acetylene balloon was connected to the reaction apparatus using a graphite rod as the anode and a platinum sheet as the cathode. The reaction was stirred at 6 mA at room temperature for 7 hours. After the reaction was complete, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The combined organic phases and the crude product obtained by rotary evaporation under reduced pressure were then purified by column chromatography to obtain the final product, 1,2-bis(p-tolueneseleno)acetylene, in 73% yield.
[0028] The proton NMR spectrum, carbon NMR spectrum, and crystal structure diagram of the obtained target product are shown below. Figure 5 , Figure 6 and Figure 7 As shown, the structural characterization data is as follows: 1 H NMR (500 MHz, Chloroform-d) d = 2.33 – 2.35 (s, 6H), 7.13 – 7.17 (d, J = 7.93, 4H), 7.42 – 7.46 (d, J = 8.17, 4H). 13 C NMR (126 MHz, Chloroform- d ) d = 21.02, 84.36, 125.42, 129.07, 130.30,137.24.HRMScalcd for C 16 H 14 Se2H + [M+H] + : 366.9504; found 366.9505. CCDC2494956
[0029] Based on the above characterization data, the structure of the target compound is inferred as follows:
[0030] Example 4 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(2-mesinetrimethyl)diselenes, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. An acetylene balloon was connected to the reaction apparatus using a graphite rod as the anode and a platinum sheet as the cathode. The reaction was carried out under stirring at 6 mA at room temperature for 7 hours. After the reaction was completed, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The combined organic phases and the crude product obtained by rotary evaporation under reduced pressure were then purified by column chromatography to obtain the final product, 1,2-bis(2-mesinetrimethyl)selenes, in 69% yield.
[0031] The proton and carbon spectra of the obtained target product are as follows: Figure 8 and Figure 9 As shown, the structural characterization data is as follows: 1 H NMR (400 MHz, Chloroform- d ) d = 2.27 – 2.28 (s, 6H), 2.49 – 2.51 (s, 12H), 6.91 – 6.93 (s, 4H). 13 C NMR (101 MHz, Chloroform- d ) d = 20.91, 79.55, 126.27, 128.89, 138.99,141.90.HRMScalcd for C 20 H 22 Se2K + [M+K] + : 460.9689; found 460.9686. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0032] Example 5 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(4-tert-butylphenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. An acetylene balloon was connected to the reaction apparatus with a graphite rod as the anode. The reaction was carried out under stirring at 6 mA at room temperature for 7 hours. After the reaction was completed, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The organic phases were combined, and the crude product was obtained by rotary evaporation under reduced pressure. Finally, the crude product was purified by column chromatography to obtain the final product 1,2-bis((4-tert-butylphenyl)selenoacetylene, in 70% yield.
[0033] The structural characterization data of the obtained target product are shown below: 1 H NMR (500 MHz, Chloroform- d ) d = 1.36 – 1.38 (s, 18H), 7.35 – 7.42(dd, J = 8.44, 28.61, 4H), 7.47 – 7.56 (dd, J = 8.41, 34.45, 4H). 13 C NMR (126 MHz, Chloroform- d ) d = 31.23, 34.48, 126.31, 128.79, 132.64,150.28.HRMScalcd for C 22 H 26 Se2Na + [M+Na] + : 473.0263; found 473.0259. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0034] Example 6 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(2-methylphenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. An acetylene balloon was connected to the reaction apparatus using a graphite rod as the anode and a platinum sheet as the cathode. The reaction was stirred at 6 mA at room temperature for 7 hours. After the reaction was complete, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The organic phases were combined, and the crude product was obtained by rotary evaporation under reduced pressure. Finally, the crude product was purified by column chromatography to obtain the final product, 1,2-bis(o-tolueneseleno)acetylene, in 43% yield.
[0035] The structural characterization data of the obtained target product are shown below: 1 H NMR (500 MHz, Chloroform- d ) d = 2.34 – 2.38 (s, 6H), 7.15 – 7.22 (d, J = 11.01, 6H), 7.74 – 7.82 (s, 2H). 13 C NMR (126 MHz, Chloroform- d ) d= 20.79, 84.05, 127.26, 127.31, 129.30,129.90, 130.26, 136.36.HRMScalcd for C 16 H 14 Se2Na + [M+Na] + : 388.9324; found388.9326. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0036] Example 7 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(2-fluorophenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. Using a graphite rod as the anode and a platinum sheet as the cathode, an acetylene balloon was connected to the reaction apparatus. The reaction was carried out under stirring at 6 mA at room temperature for 7 hours. After the reaction was completed, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The combined organic phases and the crude product obtained by rotary evaporation under reduced pressure were then purified by column chromatography to obtain the final product, 1,2-bis(2-fluorophenylselenoyl)acetylene, in 55% yield.
[0037] The structural characterization data of the obtained target product are shown below: 1 H NMR (500 MHz, Chloroform- d ) d = 7.04 – 7.10 (t, J = 8.74, 1H), 7.15 –7.22 (t, J = 7.42, 1H), 7.26 – 7.30 (d, J = 9.27, 1H), 7.69 – 7.73 (m, 1H). 13 C NMR (126 MHz, Chloroform- d ) δ = 83.60, 115.32, 115.49, 116.13,116.28, 125.60, 129.12 (d, J = 7.32), 130.57 (d, J = 3.35), 158.47, 160.41. 19 F NMR (471 MHz, Chloroform- d ) d= -108.30.HRMScalcd for C 14 H8F2Se2K + [M+K] + : 412.8562; found 412.8565. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0038] Example 8 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(3-nitrophenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. An acetylene balloon was connected to the reaction apparatus using a graphite rod as the anode and a platinum sheet as the cathode. The reaction was stirred at 6 mA at room temperature for 7 hours. After the reaction was complete, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The combined organic phases and the crude product obtained by rotary evaporation under reduced pressure were then purified by column chromatography to obtain the final product, 1,2-bis(3-nitrophenylselenoyl)acetylene, in 37% yield.
[0039] The structural characterization data of the obtained target product are shown below: 1 H NMR (500 MHz, Chloroform- d ) d = 7.49 – 7.58 (t, J = 7.83, 2H), 7.80 –7.92 (d, J = 7.91, 2H), 8.12 – 8.20 (d, J = 6.96, 2H), 8.31 – 8.46 (s, 2H). 13 C NMR (126 MHz, Chloroform- d ) d = 85.60, 122.43, 123.13, 123.67,130.33, 131.42, 134.49.HRMScalcd for C 14 H8N2O4Se2Na + [M+Na] + : 450.8712; found 450.8708. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0040] Example 9 In a three-necked flask equipped with a stirrer, 0.1 mmol of bis(3-methylphenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. Using a graphite rod as the anode and a platinum sheet as the cathode, an acetylene balloon was connected to the reaction apparatus. The reaction was carried out under stirring at 6 mA at room temperature for 7 hours. After the reaction was completed, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The combined organic phases and the crude product obtained by rotary evaporation under reduced pressure were then purified by column chromatography to obtain the final product, 1,2-bis(3-methylphenylselenoyl)acetylene, in 65% yield.
[0041] The structural characterization data of the obtained target product are shown below: 1 H NMR (500 MHz, Chloroform- d ) d = 2.35 – 2.36 (s, 6H), 7.07 – 7.09 (s, 2H), 7.20 – 7.24 (s, 2H), 7.34 – 7.38 (s, 4H). 13 C NMR (126 MHz, Chloroform- d ) d = 21.39, 125.84, 128.10, 129.08,129.28, 129.37, 139.52.HRMScalcd for C 16 H 14 Se2H + [M+H] + : 366.9504; found 366.9493. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0042] Example 10 In a three-necked flask equipped with a stirrer, 0.1 mmol of di(benzylphenyl)diselenoether, 0.2 mmol of tetrabutylammonium iodide, and 3 mL of dimethyl sulfoxide were added sequentially. Using a graphite rod as the anode and a platinum sheet as the cathode, an acetylene balloon was connected to the reaction apparatus. The reaction was carried out under stirring at 6 mA at room temperature for 7 hours. After the reaction was completed, the mixture was filtered, and the filtrate was extracted multiple times with ethyl acetate. The combined organic phases and the crude product obtained by rotary evaporation under reduced pressure were then purified by column chromatography to obtain the final product, 1,2-di(benzylseleno)acetylene, in 32% yield.
[0043] The structural characterization data of the obtained target product are shown below: 1H NMR (500 MHz, Chloroform- d ) d = 3.96 – 3.98 (s, 4H), 7.24 – 7.26 (d, J = 7.80, 5H), 7.28 – 7.32 (t, J = 6.95, 5H). 13 C NMR (126 MHz, Chloroform- d ) d = 33.85, 84.03, 127.42, 128.49, 128.98,137.41.HRMScalcd for C 16 H 14 Se2Na + [M+Na] + : 388.9324; found 388.9321. Based on the above characterization data, the structure of the target compound is inferred as follows:
[0044] The above embodiments are some examples of the method of the present invention, but they do not limit the specific implementation of the present invention. Any substitution of substituents, changes in the basic skeleton, or simplification of conditions made without departing from the spirit and principle of the present invention should be classified as equivalent substitution methods and are included within the protection scope of the present invention.
Claims
1. A method for the electrochemically promoted synthesis of selenium-phenyl-substituted alkyne derivatives, characterized in that, It includes the following steps: Tetrabutylammonium iodide, diselenyl ether derivative, and solvent were added sequentially to a three-necked flask. An acetylene balloon was then connected to the reaction system, and the anode and cathode were inserted at room temperature. The reaction was stirred for 7 hours. After the reaction, the crude product was purified by column chromatography to obtain a selenylphenyl-substituted alkyne derivative. The above reaction is shown in the following equation: ； In the formula, R is selected from one of phenyl, 4-fluorophenyl, 4-methylphenyl, 2,4,6-trimethylphenyl, 4-tert-butylphenyl, 2-methylphenyl, 2-fluorophenyl, 3-nitrophenyl, 3-methylphenyl, and benzyl; the electrolyte is selected from one of tetrabutylammonium iodide, tetrabutylammonium tetrafluoroborate, tetrabutylammonium thiocyanate, and tetrabutylammonium perchlorate; the solvent is selected from one of dimethyl sulfoxide, 1,2-dichloroethane, dichloromethane, acetonitrile, tetrahydrofuran, and ethanol; the anode electrode material is one of graphite rod and stainless steel sheet (SS); the cathode electrode material is one of stainless steel sheet (SS), platinum sheet, nickel sheet, and graphite rod.
2. The method for electrochemically promoted synthesis of selenium-phenyl-substituted alkyne derivatives according to claim 1, characterized in that, The molar ratio of the diselenyl ether derivative to the electrolyte is 1:1~2.
3. The method for electrochemically promoted synthesis of selenium-phenyl-substituted alkyne derivatives according to claim 1, characterized in that, The electrolysis current is 6-10 mA.
4. The method for electrochemically promoted synthesis of selenium-phenyl-substituted alkyne derivatives according to claim 1, characterized in that: The crude product was purified by column chromatography, using a mixture of petroleum ether and ethyl acetate as the eluent at a volume ratio of 1 to 100:1.