Preparation method and application of (hetero)aryl trifluoromethyl tellurium ether compound

Abstract

The present invention discloses a preparation method and application of (hetero)aryl trifluoromethyl tellurium ether compounds. The preparation method comprises the following steps: reacting a (hetero)aryl coronium salt, a trifluoromethyl tellurium salt, and a first solvent under light conditions, followed by a first separation and purification step after the reaction to obtain the (hetero)aryl trifluoromethyl tellurium ether. Using (hetero)aryl coronium salts and trifluoromethyl tellurium salts as raw materials, the present invention can achieve trifluoromethyl tellurylation of various types of bioactive molecules under very mild conditions without the addition of transition metal catalysts or ligands. The reaction is simple to operate, safe and efficient, with easy product purification, high yield, a wide range of substrate applicability, good functional group tolerance, and readily available, inexpensive raw materials. This provides a novel, efficient, and green strategy for the synthesis of bioactive molecules containing trifluoromethyl tellurium groups.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method and application of a (hetero)aryl trifluoromethyl tellurium ether compound. Background Art

[0002] Tellurium was discovered by Müller in 1782 and exists in trace amounts in the Earth's crust. When a trifluoromethyl group is attached to tellurium, the strong electron-withdrawing effect of the trifluoromethyl group significantly reduces the electron cloud density at the center of the tellurium atom. Compared to tellurium ethers without fluorine, the charge on the tellurium atom in the trifluoromethyl-containing tellurium ether changes from partially negative to partially positive, resulting in different properties.

[0003] Currently, the methods known for preparing trifluoromethyl telluride are very limited and can be roughly divided into two categories: direct method and indirect method. There are two main indirect methods for preparing trifluoromethyl telluride: (1) Using ArTeTeAr as the starting material, first react with NaBH4 to prepare ArTeH, and then react with CF3I in -78 o C to room temperature, the corresponding aryl trifluoromethyl tellurium ether can be prepared (J. Am. Chem. Soc. 1993, 115, 2156-2164); (2) ArTeTeAr as raw material, react with TMSCF3 in acetonitrile at room temperature to 80 oC reaction to obtain the corresponding aryl trifluoromethyl tellurium ether (Organometallics, 2017, 36, 3750-3757). There are only a few direct methods for preparing trifluoromethyltelluryl compounds: (1) using KTeCF3 as a trifluoromethyltelluryl reagent to prepare trifluoromethyl telluride ethers through nucleophilic substitution reaction (Angew. Chem. Int. Ed. 2018, 57,1381-1385); (2) using Me3SnTeCF3 as a trifluoromethyltelluryl reagent to prepare aryl trifluoromethyl telluride ethers in acetonitrile at room temperature (J. Fluorine Chem. 1999, 94, 195-198); (3) using [Me4N][TeCF3] as a trifluoromethyltelluryl reagent to react with dichloromethane, iodomethane, and methyl 4-bromobutyrate to prepare the corresponding trifluoromethyltelluride substituted products (J.Fluorine Chem. 2004, 125, 1437-1440; Z. Anorg. Allg. Chem. 2012, 638, 580-588; Org. Biomol. Chem. 2015, 13, 7027-7033); (4) Using Pd as a catalyst, the trifluoromethyltellurylation reaction of aryl halides with [Me4N][TeCF3] was achieved (Angew. Chem. Int. Ed. 2018, 57, 16903-16906); (5) Using Cu as a catalyst, the trifluoromethyltellurylation reaction of arylboronic acids with [Me4N][TeCF3] was achieved (iScience2022, 25, 105566); (6) Using NIS as an initiator, the trifluoromethyltellurylation reaction of electron-rich indoles with [Me4N][TeCF3] was achieved (ChemistrySelect 2023, 8, e202302350). Existing methods for synthesizing trifluoromethyltellurium compounds suffer from limitations such as a single reaction type, demanding conditions, the need for specialized starting materials, low yields, and a narrow substrate range. Therefore, a method with mild reaction conditions, simple operation, safety, high efficiency, and broad applicability is still needed to prepare complex molecules containing trifluoromethyltellurium groups with diverse structures. This is of great significance for the future applications of trifluoromethyltellurium-containing compounds.

[0004] Among the few trifluoromethyltellurylating agents, trifluoromethyltellurium salts, such as [Me4N][TeCF3], are currently considered the most promising. Currently, trifluoromethyltellurylation reactions using [Me4N][TeCF3] have been demonstrated for aryl halides, arylboronic acids, and electron-rich indoles. However, these reactions struggle to selectively functionalize complex aromatics. To construct more complex and diverse trifluoromethyltelluryl compounds, a novel approach based on [Me4N][TeCF3] is needed. Summary of the Invention

[0005] The purpose of the present invention is to overcome the above technical deficiencies, propose a preparation method and application of (hetero)aryl trifluoromethyl tellurium ether compounds, and solve the technical problems in the prior art of (hetero)aryl trifluoromethyl tellurium ether compounds such as harsh preparation conditions, low yield and narrow substrate range.

[0006] In a first aspect, the present invention provides a method for preparing a (hetero)aryl trifluoromethyl tellurium ether compound, comprising the following steps:

[0007] The (hetero)aryl trifluoromethyl tellurium salt and the first solvent are reacted under light conditions, and after the reaction is completed, the (hetero)aryl trifluoromethyl tellurium ether is obtained by first separation and purification.

[0008] In a second aspect, the present invention provides the use of the preparation method of the above-mentioned (hetero)aryl trifluoromethyl tellurium ether compound in the preparation of a drug having a (hetero)aryl trifluoromethyl tellurium ether structure.

[0009] Compared with the prior art, the present invention has the following beneficial effects:

[0010] This invention uses (hetero)arylstemsium salts and trifluoromethyltellurium salts as raw materials, and under very mild reaction conditions, without the addition of transition metal catalysts or ligands, to achieve trifluoromethyltellurylation of various types of bioactive molecules. This reaction is simple to operate, safe and efficient, with easy product purification, high yield, a wide range of substrate applicability, good functional group tolerance, and readily available, inexpensive raw materials. It provides a novel, efficient, and green strategy for the synthesis of bioactive molecules containing trifluoromethyltellurium groups. BRIEF DESCRIPTION OF THE DRAWINGS

[0011] Figure 1 is the Hela cell survival rate of Fenofibrate-TeCF3 prepared by the present invention at different drug concentrations;

[0012] Figure 2 is the Hela cell survival rate of Methyl Flurbiprofen-TeCF3 prepared by the present invention at different drug concentrations;

[0013] Figure 3 is the Hela cell survival rate of Etofenprox-TeCF3 prepared by the present invention at different drug concentrations;

[0014] Figure 4 is the Hela cell survival rate of Aniracetam-TeCF3 prepared by the present invention at different drug concentrations;

[0015] Figure 5 is the Hela cell survival rate of Clofibrate-TeCF3 prepared by the present invention at different drug concentrations;

[0016] Figure 6 is the Hela cell survival rate of Boscalid-TeCF3 prepared by the present invention at different drug concentrations;

[0017] Figure 7 It is the survival rate of Hela cells at different drug concentrations of Pyriproxfen-TeCF3 prepared by the present invention. DETAILED DESCRIPTION

[0018] In order to make the purpose, technical solutions and advantages of the present invention more clearly understood, the present invention will be further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention.

[0019] In a first aspect, the present invention provides a method for preparing a (hetero)aryl trifluoromethyl tellurium ether compound, comprising the following steps:

[0020] A (hetero)aryl coronium salt, a trifluoromethyl tellurium salt and a first solvent are reacted under light conditions, and after the reaction is completed, a first separation and purification is performed to obtain a (hetero)aryl trifluoromethyl tellurium ether compound; the reaction formula is as follows:

[0021] ;

[0022] Where R 1 and R 2 are all phenyl, and R 1 and R 2 The ends of the alkyl radicals are not connected, or are directly connected to form a ring, or are connected to form a ring by -O-, or are connected to form a ring by -S-; Ar is one of substituted or unsubstituted phenyl, pyridyl, xanthanone, indolyl, benzothiophenyl and thienyl, and the substituents include at least one of alkyl, alkoxy, phenoxy, ester, cyano, halogen, ketocarbonyl, amide, cyclic amide, sulfonamide and imide.

[0023] The reaction system of the present invention requires only the addition of an aryl coronium salt, a trifluoromethyltellurium salt, and a solvent to achieve trifluoromethyltellurylation of various bioactive molecules. This reaction system also offers advantages such as simple raw material sources, low cost, mild reaction conditions, simple operation, good functional group tolerance, and environmental friendliness.

[0024] In this embodiment, the (hetero)aryl coronium salt is one of a thianthrene coronium salt containing a (hetero)aryl group, a phenoxathiol coronium salt containing a (hetero)aryl group, a dibenzothiophene coronium salt containing a (hetero)aryl group, and a diphenyl coronium salt containing a (hetero)aryl group.

[0025] Preferably, the (hetero)aryl coronium salt is a thianthrene coronium salt containing a (hetero)aryl group, and the reaction formula involved in the preparation method of the (hetero)aryl trifluoromethyl tellurium ether compound is as follows:

[0026] .

[0027] In some embodiments of the present invention, the preparation method of the thianthrene-containing (hetero)aryl salt comprises the following steps:

[0028] The (hetero)aromatic hydrocarbon, thianthrene oxide, acid anhydride and optional acid are reacted in a second solvent, and the reaction is followed by a second separation and purification to obtain a thianthrene-based thianthrene salt containing a (hetero)aromatic group; the reaction formula is as follows:

[0029] .

[0030] Preferably, the acid anhydride is at least one of trifluoromethanesulfonic anhydride or trifluoroacetic anhydride.

[0031] Preferably, the acid is trifluoromethanesulfonic acid.

[0032] Preferably, the molar ratio of (hetero)arene to thianthrene oxide is 1:(0.1-10), including but not limited to 1:0.1, 1:0.5, 1:1, 1:1.5, 1:2, 1:4, 1:6, 1:8, 1:10, etc.

[0033] Preferably, the ratio of the (hetero)aromatic hydrocarbon to the total amount of the acid and the anhydride is (1-6) mol:1 L, including but not limited to 1 mol:1 L, 2 mol:1 L, 3 mol:1 L, 4 mol:1 L, 5 mol:1 L, 6 mol:1 L, etc.

[0034] Preferably, the usage ratio of the (hetero)aromatic hydrocarbon to the second solvent is (0.05-0.3) mol:1 L, including but not limited to 0.05 mol:1 L, 0.1 mol:1 L, 0.15 mol:1 L, 0.2 mol:1 L, 0.25 mol:1 L, 0.3 mol:1 L, etc.

[0035] Preferably, the second solvent is one of acetonitrile or dichloromethane.

[0036] Preferably, a mixture of (hetero)aromatic hydrocarbon, thianthrene oxide, second solvent, acid anhydride and optional acid is firstly heated at -50 to -40 o C for 0.5-2 hours, then warm to room temperature for 8-24 hours.

[0037] Preferably, the second separation and purification method includes at least one of extraction, washing, column chromatography, and recrystallization.

[0038] Wherein, washing comprises at least one of water washing or washing with a saturated sodium trifluoromethanesulfonate aqueous solution.

[0039] Wherein, the extractant is at least one of dichloromethane or acetonitrile.

[0040] The eluent used for column chromatography is a mixed solvent of dichloromethane and acetonitrile, and the volume ratio of dichloromethane to acetonitrile is (1-5):1, including but not limited to 1:1, 2:1, 3:1, 4:1, 5:1, etc.

[0041] The recrystallization solvent is a mixed solvent of dichloromethane and methyl tert-butyl ether, and the volume ratio of dichloromethane to methyl tert-butyl ether is 1:(10-25), including but not limited to 1:10, 1:15, 1:20, 1:25, etc.

[0042] In some more specific embodiments of the present invention, the preparation method of the thianthrene-containing (hetero)aryl salt comprises the following steps:

[0043] In a protective atmosphere, aromatic hydrocarbon or heteroaromatic hydrocarbon, thianthrene oxide and second solvent are added to the reaction vessel in sequence, and the temperature is lowered to -50 to -40 o C, then add anhydride and optional acid, at -50 ~ -40 o C for 0.5-2 hours, then warm to room temperature for 8-24 hours. After the reaction is complete, the reaction solution is diluted with a diluent, then neutralized with a saturated aqueous sodium bicarbonate solution. The organic layer is then washed with water, and the aqueous layer is extracted with an extractant. After combining the organic layers, the organic layer is optionally washed with a saturated aqueous sodium trifluoromethanesulfonate solution, then dried over anhydrous sodium sulfate, and excess solvent removed under reduced pressure. Finally, column chromatography or recrystallization is performed to obtain a thianthrene-containing (hetero)aryl salt. The diluent is at least one of dichloromethane and acetonitrile.

[0044] In this embodiment, the trifluoromethyl tellurium salt is [Me4N][TeCF3] (ie, trifluoromethyl tellurium tetramethyl ammonium salt), [ n-Bu4N][TeCF3], [PNP][TeCF3] and [(dibenzo-18-crown-6)K][TeCF3].

[0045] In this embodiment, the first solvent is one of N,N-dimethylformamide, dimethyl carbonate, acetonitrile, N,N-dimethylacetamide, tetrahydrofuran, n-hexane, ethyl acetate, 1,2-dichloroethane, diethylene glycol dimethyl ether, ethyl ether, methyl tert-butyl ether, dichloromethane, N-methylpyrrolidone, 1,4-dioxane, hexafluoroisopropanol, benzene, toluene, and xylene, preferably N,N-dimethylformamide.

[0046] In this embodiment, the molar ratio of the (hetero)arylstems salt to the trifluoromethyltellurium salt is 1:(0.5-3), including but not limited to 1:0.5, 1:1, 1:1.4, 1:2, 1:2.5, 1:3, etc.

[0047] In this embodiment, the usage ratio of the (hetero)arylstephonium salt to the first solvent is (0.025-0.3) mol:1 L, including but not limited to 0.025 mol:1 L, 0.05 mol:1 L, 0.075 mol:1 L, 0.1 mol:1 L, 0.125 mol:1 L, 0.15 mol:1 L, 0.175 mol:1 L, 0.2 mol:1 L, 0.225 mol:1 L, 0.25 mol:1 L, 0.275 mol:1 L, 0.3 mol:1 L, etc.

[0048] In this embodiment, the wavelength of the light source used in the illumination conditions is 365-600 nm, including but not limited to 365-370 nm, 380-385 nm, 395-400 nm, 460-465 nm, blue LED (450-495 nm), and green LED (520-570 nm); the power is 5-50 W, including but not limited to 5 W, 10 W, 15 W, 20 W, 25 W, 30 W, 35 W, 40 W, 45 W, and 50 W.

[0049] In this embodiment, the reaction temperature is -40 ~ 40 o C, including but not limited to -40 o C, -30 o C, -20 o C, -10 o C.0 o C. 10 o C. 20 o C. 30 o C. 40 oC, etc.; the time is 4-24 hours, including but not limited to 4 hours, 8 hours, 12 hours, 16 hours, 20 hours, 24 hours, etc.

[0050] In this embodiment, the process of reacting the (hetero)arylstemium salt, the trifluoromethyltellurium salt, and the first solvent under light conditions is carried out under a protective atmosphere. The present invention does not limit the type of protective atmosphere, and those skilled in the art can select one based on actual circumstances. For example, the protective atmosphere can be nitrogen.

[0051] In this embodiment, the first separation and purification method includes: column chromatography.

[0052] Preferably, in the first separation and purification process, the eluent used in column chromatography is at least one of petroleum ether or ethyl acetate.

[0053] In this embodiment, the structural formula of the (hetero)aryl trifluoromethyl tellurium ether compound is selected from but not limited to one of the following:

[0054]

[0055] .

[0056] In a second aspect, the present invention provides the use of the preparation method of the above-mentioned (hetero)aryl trifluoromethyl tellurium ether compound in the preparation of a drug having a (hetero)aryl trifluoromethyl tellurium ether structure.

[0057] In this embodiment, the drug is an anticancer drug. The (hetero)aryl trifluoromethyl tellurium ether compounds of the present invention have high inhibitory activity against cancer cells and can be used to prepare anticancer drugs.

[0058] Furthermore, the cancer is cervical cancer. The present invention conducts a biological activity evaluation on the above-mentioned trifluoromethyltellurium-containing compounds synthesized above, and the results show that such compounds have high inhibitory activity against cervical cancer cells.

[0059] Unless otherwise specified, the raw materials, reagents, or devices used in the following examples can be obtained from conventional commercial sources or by existing known methods.

[0060] Example 1

[0061]

[0062] Step 1: Under nitrogen protection, 1-cyano-4-phenoxybenzene (5.2 mmol, 1.0 g), thianthrene oxide (5.2 mmol, 1.2 g) and DCM (20 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, then trifluoromethanesulfonic anhydride (1 mL) was added and the mixture was stirred at -40o The reaction mixture was allowed to react at 40 °C for 1 hour, then warmed to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (40 mL). The organic layer was washed once with water (40 mL), and the aqueous layer was extracted twice with DCM (40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. Excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:25, 50 mL) to obtain the corresponding coronium salt (white solid, 2.1 g, 73%).

[0063] Step 2: In a glove box, 1-cyano-4-phenoxybenzthianthrene (0.1 mmol, 56.0 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and DMF (0.5 mL) were added to a 10 mL reaction tube in sequence. The reaction temperature was controlled at 30-32 o C. The reaction tube was removed from the glove box and irradiated with a green LED (520-570 nm, 5 W) for 12 hours. After completion of the reaction, the product was purified by silica gel column chromatography using petroleum ether / ethyl acetate (20:1) as the eluent to obtain the trifluoromethyltellurium-modified 1-cyano-4-phenoxybenzene molecule (32.5 mg, 83% yield, as a pale yellow oil). 1 H NMR (500 MHz, CDCl3) δ 8.02 (d, J = 8.46 Hz, 2H), 7.65 (d, J = 8.74Hz, 2H), 7.08 (d, J = 8.72 Hz, 2H), 7.01 (d, J = 8.49 Hz, 2H). 19 F NMR (471MHz, CDCl3) δ -25.7 (s, 3F). 13 C NMR (126 MHz, CDCl3) δ 160.5, 157.4, 144.0,134.5, 121.4, 119.1, 118.7, 107.2, 104.3, 100.1 (q, J = 354.7 Hz).

[0064] Example 2

[0065]

[0066] Step 1: Under nitrogen protection, 1-cyano-4-phenoxybenzene (5.2 mmol, 1.0 g), thianthrene oxide (5.2 mmol, 1.2 g) and DCM (20 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, then trifluoromethanesulfonic anhydride (1 mL) was added, and the mixture was stirred at -40 o The reaction was allowed to proceed at 40°C for 1 hour, then the temperature was raised to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (40 mL). The organic layer was washed once with water (40 mL), and the aqueous layer was extracted twice with DCM (40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. Excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:25, 50 mL) to obtain the corresponding coronium salt (white solid, 2.1 g, 73%).

[0067] Step 2: In a glove box, 1-cyano-4-phenoxybenzthianthrene (0.1 mmol, 56.0 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and DMF (0.5 mL) were added to a 10 mL reaction tube in sequence. The reaction tube was removed from the glove box and irradiated under 365-370 nm (5 W), 380-385 nm (5 W), 395-400 nm (5 W), 460-465 nm (5 W), and blue LED (450-495 nm, 5 W) for 12 hours. The reaction temperature was controlled at 30-32 o After the reaction, the product was purified by silica gel column chromatography using petroleum ether / ethyl acetate (20:1) as the eluent to obtain trifluoromethyltellurium-modified 1-cyano-4-phenoxybenzene molecules (yields of 72%, 65%, 67%, 76%, and 73%, respectively). 1 H NMR (500 MHz, CDCl3) δ 8.02 (d, J = 8.46 Hz, 2H), 7.65 (d, J =8.74 Hz, 2H), 7.08 (d, J = 8.72 Hz, 2H), 7.01 (d, J = 8.49 Hz, 2H). 19 F NMR (471 MHz, CDCl3) δ -25.7 (s, 3F). 13C NMR (126 MHz, CDCl3) δ 160.5, 157.4, 144.0, 134.5, 121.4, 119.1, 118.7, 107.2, 104.3, 100.1 (q, J = 354.7 Hz).

[0068] Example 3

[0069]

[0070] Step 1: Under nitrogen protection, pyriproxyfen (1 mmol, 321.4 mg), thianthrene oxide (1 mmol, 232.3 mg) and acetonitrile (5 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, trifluoroacetic anhydride (0.42 mL) and trifluoromethanesulfonic acid (0.26 mL) were added in sequence, and the mixture was stirred at -40 o The reaction was allowed to proceed at 40°C for 1 hour, then the temperature was raised to room temperature for 12 hours. After the reaction was complete, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and washed twice with saturated aqueous sodium trifluoromethanesulfonate (20 mL). The organic phase was dried over anhydrous sodium sulfate, and the excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:15, 50 mL) to obtain the corresponding coronium salt (white solid, 388.8 mg, 57%).

[0071] Step 2: In a glove box, pyriproxyfen thianthrene (0.1 mmol, 68.6 mg), [PNP][TeCF3] (0.14 mmol, 104.9 mg) and DMAc (0.5 mL) were added to a 10 mL reaction tube in sequence. The reaction tube was removed from the glove box and irradiated with a green LED (520-570 nm, 5 W) for 12 hours. The reaction temperature was controlled at 30-32 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether / ethyl acetate (20:1) as eluent to obtain the trifluoromethyltellurium-modified pyriproxyfen molecule (30.1 mg of a pale yellow oily liquid, 58% yield). 1H NMR (500MHz, CDCl3) δ 8.16-8.15 (m, 1H), 7.89 (d, J = 8.75 Hz, 2H), 7.57 (td, J =7.48 Hz, J = 1.93 Hz, 1H), 6.98 (q, J =9.15 Hz, 4H), 6.86 (d, J = 8.47 Hz, 3H), 6.76 (d, J = 8.29 Hz, 1H), 5.63-5.57 (m, 1H), 4.22-4.07 (m, 2H), 1.49 (d, J = 6.41 Hz, 3H). 19 F NMR (471 MHz, CDCl3) δ -26.2 (s, 3F). 13 C NMR (126 MHz, CDCl3) δ 163.3, 160.9, 156.1, 148.9, 146.9, 143.7, 138.9, 121.7, 118.6,116.9, 116.1, 111.8, 101.3, 102.7 (q, J = 353.7 Hz), 71.2, 69.3, 17.1.

[0072] Example 4

[0073]

[0074] Step 1: Under nitrogen protection, methylflurbiprofen (MethylFlurbiprofen, 1 mmol, 258.3 mg), thianthrene oxide (1 mmol, 232.3 mg) and acetonitrile (5 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, trifluoroacetic anhydride (0.42 mL) and trifluoromethanesulfonic acid (0.26 mL) were added, and the mixture was stirred at -40 o The reaction mixture was allowed to react at 40°C for 1 hour, then warmed to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and washed twice with saturated aqueous sodium trifluoromethanesulfonate (20 mL). The organic phase was dried over anhydrous sodium sulfate, and the excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:25, 50 mL) to obtain the corresponding coronium salt (white solid, 335.6 mg, 54%).

[0075] Step 2: In a glove box, methylflurbiprofen thianthrene salt (0.1 mmol, 62.3 mg), [(dibenzo-18-crown-6)K][TeCF3] (0.14 mmol, 83.5 mg) and DMF (0.5 mL) were added to a 10 mL reaction tube in sequence. The reaction tube was removed from the glove box and irradiated with a green LED (520-570 nm, 5 W) for 12 hours. The reaction temperature was controlled at 30-32 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether / ethyl acetate (10:1) as eluent to obtain trifluoromethyltellurium-modified methylflurbiprofen (30.0 mg of pale yellow oily liquid, 66% yield). 1 H NMR (500 MHz, CDCl3) δ 8.05 (d, J = 8.00 Hz, 2H), 7.51 (d,J = 7.13 Hz, 2H), 7.39 (t, J =8.01 Hz, 1H), 7.18-7.13 (m, 2H), 3.77 (q, J =7.28 Hz, 1H), 3.71 (s, 3H), 1.55 (d, J = 7.14 Hz, 3H). 19 F NMR (471 MHz, CDCl3)δ -25.3 (s, 3F), -117.2 (m, 1F). 13 C NMR (126 MHz, CDCl3) δ 174.3, 159.7 (d, J= 249.3 Hz), 142.7 (d, J = 7.7 Hz), 141.5, 137.5, 130.7 (d, J = 7.7 Hz), 130.3 (d, J = 3.1 Hz), 126.6 (d, J = 13.3 Hz), 123.8 (d, J = 3.3 Hz), 115.4 (d, J = 23.5 Hz), 109.0, 102.8 (q, J = 354.3 Hz), 52.3, 45.0, 18.4.

[0076] Example 5

[0077]

[0078] Step 1: Under nitrogen protection, add etofenprox (1 mmol, 376.5 mg), thianthrene oxide (1 mmol, 232.3 mg) and acetonitrile (5 mL) in sequence to a 25 mL round-bottom flask, cool to -40 o C, trifluoroacetic anhydride (0.42 mL) and trifluoromethanesulfonic acid (0.26 mL) were added in sequence, and the mixture was stirred at -40 o The reaction was allowed to proceed at 40°C for 1 hour, then the temperature was raised to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and washed twice with saturated aqueous sodium trifluoromethanesulfonate (20 mL). The organic phase was dried over anhydrous sodium sulfate, and the excess solvent was removed under reduced pressure. The residue was separated by column chromatography using dichloromethane / acetonitrile (3:1) as the eluent to obtain the corresponding coronium salt (white solid, 592.7 mg, 80%).

[0079] Step 2: In a glove box, add thiophenethrin (0.1 mmol, 74.1 mg), [n-Bu4N][TeCF3] (0.14 mmol, 61.8 mg) and DMF (0.5 mL) to a 10 mL reaction tube. Remove the reaction tube from the glove box and irradiate it with a green LED (520-570 nm, 5 W) for 12 hours. The reaction temperature is controlled at 30-32 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether / ethyl acetate (10:1) as eluent to obtain trifluoromethyltellurium-modified ethoxythrin (37.0 mg as a pale yellow oily liquid, 50% yield). 1 H NMR(500 MHz, CDCl3) δ 7.73 (d, J = 2.08 Hz, 1H), 7.35-7.32 (m, 3H), 7.29-7.26(m, 2H), 7.11 (t, J = 7.39 Hz, 1H), 7.01 (d, J = 7.97 Hz, 2H), 6.93-6.89 (m,2H), 6.79 (d, J = 8.60 Hz, 1H), 4.45 (s, 2H), 4.07 (q, J = 6.91 Hz, 2H), 3.42(s, 2H), 1.41 (t, J = 6.95 Hz, 3H), 1.31 (s, 6H). 19F NMR (471 MHz, CDCl3) δ -24.8 (s, 3F). 13 C NMR (126 MHz, CDCl3) δ 157.5, 157.4, 156.4, 142.2, 141.0,135.3, 129.9, 128.5, 127.2, 123.4, 122.2, 119.1, 117.9, 117.8, 114.1, 110.9, 103.6 (q, J = 352.9 Hz), 80.1, 72.9, 65.0, 38.8, 26.3, 14.9.

[0080] Example 6

[0081]

[0082] Step 1: Under nitrogen protection, fenofibrate (1 mmol, 360.8 mg), thianthrene oxide (1 mmol, 232.3 mg) and DCM (5 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, trifluoromethanesulfonic anhydride (0.2 mL) was added, and the mixture was stirred at -40 o The reaction mixture was allowed to react at 40°C for 1 hour, then warmed to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and dried over anhydrous sodium sulfate. Excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:15, 50 mL) to obtain the corresponding coronium salt (white solid, 300.0 mg, 41%).

[0083] Step 2: In a glove box, fenofibrate thianthrene salt (0.1 mmol, 72.5 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and DMAc (0.5 mL) were added to a 10 mL reaction tube. The reaction tube was removed from the glove box and irradiated with a green LED (520-570 nm, 5 W) for 12 hours. The reaction temperature was controlled at 30-32 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether / ethyl acetate (10:1) as eluent to obtain trifluoromethyltellurium-modified fenofibrate (45.6 mg of a pale yellow oily liquid, 82% yield).1 H NMR (500MHz, CDCl3) δ 8.19 (s, 1H), 7.75-7,70 (m, 3H), 7.46 (d, J =8.42 Hz, 2H), 6.79(d, J = 8.64 Hz, 1H), 5.11-5.05 (m, 1H), 1.69 (s, 6H), 1.20 (d, J = 6.32 Hz,6H). 19 F NMR (471 MHz, CDCl3) δ -24.8 (s, 3F). 13 C NMR (126 MHz, CDCl3) δ 193.4,172.3, 158.7, 139.7, 139.0, 135.8, 132.5, 132.4, 131.4, 128.8, 117.4, 114.2,104.2 (q, J = 353.6 Hz), 81.6, 69.9, 25.4, 21.6.

[0084] Example 7

[0085]

[0086] Step 1: Under nitrogen protection, clofibrate (1 mmol, 242.7 mg), thianthrene oxide (1 mmol, 232.3 mg) and DCM (5 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, trifluoromethanesulfonic anhydride (0.2 mL) was added, and the mixture was stirred at -40 o The reaction mixture was allowed to react at 40°C for 1 hour, then warmed to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and dried over anhydrous sodium sulfate. Excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:10, 50 mL) to obtain the corresponding coronium salt (white solid, 436.0 mg, 72%).

[0087] Step 2: In a glove box, clofibrate thianthrene thiophene salt (0.1 mmol, 60.7 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and THF (0.5 mL) were added to a 10 mL reaction tube in sequence. The reaction tube was removed from the glove box and irradiated with a green LED (520-570 nm, 5 W) for 12 hours. The reaction temperature was controlled at 30-32 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether / ethyl acetate (20:1) as eluent to obtain trifluoromethyltellurium-modified clofibrate (40.2 mg of light yellow oily liquid, 92% yield). 1 H NMR (500MHz, CDCl3) δ 7.62 (d, J = 2.35 Hz, 1H), 7.18 (dd, J =8.77 Hz, J =2.45 Hz, 1H), 6.67 (d, J = 8.80 Hz, 1H), 4.23 (q, J =7.13 Hz, 2H), 1.62 (s, 6H), 1.24 (t, J = 7.12 Hz, 3H). 19 F NMR (471 MHz, CDCl3) δ -25.0 (s, 3F). 13 C NMR (126 MHz, CDCl3) δ 173.3, 153.4, 135.5, 129.5, 129.1, 116.5, 109.6, 104.6 (q, J = 353.4Hz), 81.4, 62.0, 25.3, 14.2.

[0088] Example 8

[0089]

[0090] Step 1: Under nitrogen protection, Aniracetam (1 mmol, 219.2 mg), thianthrene oxide (1 mmol, 232.3 mg) and acetonitrile (5 mL) were added to a 25 mL round-bottom flask in sequence and the temperature was lowered to -40 o C, trifluoroacetic anhydride (0.42 mL) and trifluoromethanesulfonic acid (0.26 mL) were added in sequence, and the mixture was stirred at -40 oThe reaction was allowed to proceed at 40°C for 1 hour, then the temperature was raised to room temperature for 12 hours. After the reaction was complete, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and washed twice with saturated aqueous sodium trifluoromethanesulfonate (20 mL). The organic phase was dried over anhydrous sodium sulfate, and the excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:15, 50 mL) to obtain the corresponding coronium salt (white solid, 424.5 mg, 73%).

[0091] Step 2: In a glove box, aniracetam thianthrene salt (0.1 mmol, 58.4 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and DMF (0.5 mL) were added to a 10 mL reaction tube. The reaction tube was removed from the glove box and irradiated with a blue LED (450-495 nm, 5 W) for 12 hours. The reaction temperature was controlled at 0 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether / ethyl acetate (10:1) as eluent to obtain trifluoromethyltellurium-modified aniracetam (31.0 mg of light yellow oily liquid, 75% yield). 1 H NMR (500MHz, CDCl3) δ 8.06 (d, J = 1.86 Hz, 1H), 7.71 (dd, J =8.58 Hz, J =2.05 Hz, 1H), 6.92 (d, J = 8.68 Hz, 1H), 3.96 (d, J =7.09 Hz, 2H), 3.93 (s, 3H), 2.62 (t, J = 8.01 Hz, 2H), 2.18-2.12 (m, 2H). 19 F NMR (471 MHz, CDCl3) δ -25.0 (s,3F). 13 C NMR (126 MHz, CDCl3) δ 174.7, 169.1, 162.0, 140.1, 133.3, 128.6,109.2, 103.6 (q, J = 354.8 Hz), 102.7, 56.6, 46.9, 33.5, 17.8.

[0092] Example 9

[0093]

[0094] Step 1: Under nitrogen protection, gemfibrozil methyl ester (1 mmol, 264.4 mg), thianthrene oxide (1.5 mmol, 348.5 mg) and acetonitrile (5 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, trifluoroacetic anhydride (0.42 mL) and trifluoromethanesulfonic acid (0.26 mL) were added in sequence, and the mixture was stirred at -40 o The reaction was allowed to proceed at 40°C for 1 hour, then the temperature was raised to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and washed twice with saturated aqueous sodium trifluoromethanesulfonate (20 mL). The organic phase was dried over anhydrous sodium sulfate, and the excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:25, 50 mL) to obtain the corresponding coronium salt (white solid, 405 mg, 68%).

[0095] Step 2: In a glove box, gemfibrozil methyl thianthrene salt (0.1 mmol, 62.9 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and DMF (0.5 mL) were added to a 10 mL reaction tube. The reaction tube was removed from the glove box and irradiated with a green LED (520-570 nm, 5 W) for 12 hours. The reaction temperature was controlled at 30-32 o After the reaction, the product was purified by silica gel column chromatography using petroleum ether / ethyl acetate (10:1) as eluent to obtain trifluoromethyltellurium-modified gemfibrozil methyl ester (30.8 mg of pale yellow oily liquid, 67% yield). 1 H NMR (500 MHz, CDCl3) δ 7.84 (s, 1H), 6.80 (s, 1H), 3.95 (t, J =5.81 Hz,2H), 3.66 (s, 3H), 2.59 (s, 3H), 2.17 (s, 3H), 1.78-1.69 (m, 4H), 1.22 (s,6H). 19 F NMR (471 MHz, CDCl3) δ -25.9 (s, 3F).

[0096] Example 10

[0097]

[0098] Step 1: Under nitrogen protection, biphenyl (1 mmol, 154.2 mg), thianthrene oxide (1 mmol, 232.3 mg) and DCM (20 mL) were added to a 25 mL round-bottom flask in sequence, and the temperature was lowered to -40 o C, trifluoromethanesulfonic anhydride (0.2 mL) was added, and the mixture was stirred at -40 o The reaction was allowed to proceed at 4°C for 1 hour, then the temperature was raised to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and dried over anhydrous sodium sulfate. Excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:25, 50 mL) to obtain the corresponding thiazolium salt (white solid, 466.7 mg, 90%).

[0099] Step 2: In a glove box, add biphenylthianthrene coronium salt (0.1 mmol, 51.8 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and acetonitrile (0.5 mL) in sequence to a 10 mL reaction tube. Remove the reaction tube from the glove box and place it under green LED (520-570 nm, 5 W) for 8 hours. The reaction temperature is controlled at 30-32 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether as eluent to obtain a trifluoromethyltellurium-modified biphenyl molecule (15.2 mg yellow oily liquid, 43% yield). 1 H NMR (500 MHz, CDCl3) δ 8.07 (d,J = 8.14 Hz, 2H), 7.61-7.56 (m, 4H), 7.47 (t, J = 7.73 Hz, 2H), 7.39 (t, J =7.35 Hz, 1H). 19 F NMR (471 MHz, CDCl3) δ -25.4 (s, 3F). 13 C NMR (126 MHz, CDCl3)δ 143.3, 142.0, 140.1, 129.1, 128.7, 128.2, 127.4, 108.5, 102.8 (q, J = 353.5Hz).

[0100] Example 11

[0101]

[0102] Step 1: Under nitrogen protection, add boscalid (1 mmol, 343.2 mg), thianthrene oxide (1 mmol, 232.3 mg) and acetonitrile (5 mL) into a 25 mL round-bottom flask in sequence, and cool to -40 o C, trifluoroacetic anhydride (0.42 mL) and trifluoromethanesulfonic acid (0.26 mL) were added in sequence, and the mixture was stirred at -40 o The reaction mixture was allowed to react at 40°C for 1 hour, then warmed to room temperature for 12 hours. After completion of the reaction, the reaction solution was diluted with DCM (20 mL) and neutralized with saturated aqueous sodium bicarbonate (20 mL). The organic layer was washed once with water (20 mL), and the aqueous layer was extracted twice with DCM (20 mL). The organic layers were combined and washed twice with saturated aqueous sodium trifluoromethanesulfonate (20 mL). The organic phase was dried over anhydrous sodium sulfate, and the excess solvent was removed under reduced pressure. The residue was recrystallized from a mixture of dichloromethane and methyl tert-butyl ether (1:25, 50 mL) to obtain the corresponding coronium salt (white solid, 671 mg, 95%).

[0103] Step 2: In a glove box, add boscalid thianthrene salt (0.1 mmol, 70.8 mg), [Me4N][TeCF3] (0.14 mmol, 37.9 mg) and DMF (0.5 mL) to a 10 mL reaction tube. Remove the reaction tube from the glove box and irradiate it with a green LED (520-570 nm, 5 W) for 12 hours. The reaction temperature is controlled at 30-32 o After the reaction, the product was separated and purified by silica gel column chromatography using petroleum ether / ethyl acetate (2:1) as the eluent to obtain the trifluoromethyltellurium-modified boscalid molecule (16.7 mg white solid, 31% yield). 1 H NMR (500 MHz, CDCl3) δ 8.51 (d, J = 8.4 Hz, 1H), 8.45 (dd, J = 4.8 Hz, 1.7 Hz, 1H), 8.34(s, 1H), 8.16 (d, J = 7.4 Hz, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.89 (s, 1H), 7.46 (d, J = 8.3 Hz, 2H), 7.36-7.33 (m, 3H).19 F NMR (471 MHz, CDCl3) δ -25.5(s, 3F).

[0104] In summary, it can be seen from Examples 1-11 that the method provided by the present invention can achieve trifluoromethyltellurylation of various types of bioactive molecules.

[0105] In other embodiments of the present invention, the following typical reaction products can also be obtained, and their preparation processes are not listed one by one:

[0106] .

[0107] experimental group

[0108] The bioactivity of the synthesized trifluoromethyltellurium-containing molecules was evaluated using HeLa cells, a cervical cancer cell line, as a model cell. The bioactivity test steps are as follows:

[0109] Step 1: Rinse the culture dish with PBS, remove the PBS with a pipette, add 0.25% EDTA and digest for 2 minutes. Aspirate the EDTA again, add 1 mL of culture medium, and prepare 2-3 mL of culture medium for later use. Prepare a 96-well plate and isolate the outermost circle with PBS to promote the growth of cells at the edge and reduce external influences. Select one area and add PBS as a blank control. Divide the remaining area into five areas, add 100 μL of culture medium and different concentrations of drug to each area, and then add cells to each grid except the outer grid. Incubate the cells after plating for one day.

[0110] Step 2: Aspirate the original drug solution and wash twice with PBS. Add 10 μL of thiazolyl blue (MTT) DMSO solution (5 mg / mL) and 90 μL of culture medium to each well and incubate for 3 hours. Discard the culture medium and add 100 μL of DMSO to each well. Wrap the culture dish with tin foil and newspaper and place it on a shaker to mix for 10 minutes. Calculate the cell survival rate. Test results are shown in Figure 1-7 and Table 1.

[0111] Table 1

[0112]

[0113] pass Figure 1-7As shown in Table 1, the (hetero)aryl trifluoromethyltellurium ether compounds synthesized in this invention all exhibit high inhibitory activity against HeLa cells. Among them, trifluoromethyltellurium-modified aniracetam (Aniracetam-TeCF3) and boscalid (Boscalid-TeCF3) exhibited the highest inhibitory activity against HeLa cells. After co-culturing them with model cells for one day, the viability of HeLa cells was assessed, and their IC50 values ​​were calculated to be 2.35±0.07 μmol / L and 8.18±0.05 μmol / L, respectively. This demonstrates the significant potential research value of incorporating trifluoromethyltellurium groups into bioactive molecules.

[0114] The specific embodiments of the present invention described above do not limit the scope of protection of the present invention. Any other corresponding changes and modifications made based on the technical concept of the present invention should be included in the scope of protection of the claims of the present invention.

Claims

1. A method for preparing an aryl or heteroaryl trifluoromethyl tellurium ether compound, characterized in that: The following steps are involved: The aryl or heteroaryl trifluoromethyl tellurium salt, the trifluoromethyl tellurium salt and the first solvent are reacted under light conditions, and after the reaction is completed, the aryl or heteroaryl trifluoromethyl tellurium ether compound is obtained by first separation and purification; wherein, The aryl or heteroaryl coronium salt is a thianthrene coronium salt containing an aryl or heteroaryl group; The trifluoromethyl tellurium salt is [Me4N][TeCF3], [ n -Bu4N][TeCF3]; The wavelength of the light source used in the illumination conditions is 365-600 nm; The reaction formula is as follows: ； Where, is an aryl group or a heteroaryl group.

2. The method for preparing the aryl or heteroaryl trifluoromethyl tellurium ether compound according to claim 1, characterized in that: The preparation method of the thianthrene-based coronium salt containing an aryl or heteroaryl group comprises the following steps: Aromatic hydrocarbon or heteroaromatic hydrocarbon, thianthrene oxide, acid anhydride and optional acid are reacted in a second solvent, and after the reaction, a second separation and purification is performed to obtain a thianthrene-based coronium salt containing an aromatic or heteroaromatic group; wherein, The acid anhydride is at least one of trifluoromethanesulfonic anhydride or trifluoroacetic anhydride; The acid is trifluoromethanesulfonic acid; The reaction formula is as follows: ； Where, is an aryl group or a heteroaryl group.

3. The method for preparing the aryl or heteroaryl trifluoromethyl tellurium ether compound according to claim 2, characterized in that: The second solvent is one of acetonitrile or dichloromethane; and / or, The molar ratio of the aromatic hydrocarbon or heteroaromatic hydrocarbon to the thianthrene oxide is 1:(0.1-10); and / or, The ratio of the aromatic hydrocarbon or heteroaromatic hydrocarbon to the total amount of the acid and the acid anhydride is (1-6) mol:1L; and / or, The usage ratio of the aromatic hydrocarbon or heteroaromatic hydrocarbon to the second solvent is (0.05-0.3) mol:1L.

4. The method for preparing the aryl or heteroaryl trifluoromethyl tellurium ether compound according to claim 2, wherein: The process of reacting aromatic hydrocarbon or heteroaromatic hydrocarbon, thianthrene oxide, acid anhydride and optional acid in a second solvent comprises: firstly reacting a mixture of aromatic hydrocarbon or heteroaromatic hydrocarbon, thianthrene oxide, a second solvent, acid anhydride and optional acid at -50 to -40 o C for 0.5-2 hours, then warm to room temperature for 8-24 hours.

5. The method for preparing the aryl or heteroaryl trifluoromethyl tellurium ether compound according to claim 2, wherein: The second separation and purification method includes at least one of extraction, washing, column chromatography, and recrystallization; wherein, The extractant is at least one of dichloromethane or acetonitrile; and / or, The washing comprises at least one of water washing or saturated sodium trifluoromethanesulfonate aqueous solution washing; and / or, The eluent used for the column chromatography is a mixed solvent of dichloromethane and acetonitrile, and the volume ratio of dichloromethane to acetonitrile is (1-5):1; and / or, The solvent used for the recrystallization is a mixed solvent of dichloromethane and methyl tert-butyl ether, and the volume ratio of dichloromethane to methyl tert-butyl ether is 1:(10-25).

6. The method for preparing an aryl or heteroaryl trifluoromethyl tellurium ether compound according to claim 1, wherein: The molar ratio of the aryl or heteroaryl coronium salt to the trifluoromethyltellurium salt is 1:(0.5-3); and / or, The first solvent is one of N,N-dimethylformamide, dimethyl carbonate, acetonitrile, N,N-dimethylacetamide, tetrahydrofuran, n-hexane, ethyl acetate, 1,2-dichloroethane, diethylene glycol dimethyl ether, ethyl ether, methyl tert-butyl ether, dichloromethane, N-methylpyrrolidone, 1,4-dioxane, hexafluoroisopropanol, benzene, toluene or xylene; and / or, The usage ratio of the aryl or heteroaryl saponinium salt to the first solvent is (0.025-0.3) mol:1 L.

7. The method for preparing an aryl or heteroaryl trifluoromethyl tellurium ether compound according to claim 1, wherein: The power of the light source used in the illumination conditions is 5-50 W; the reaction temperature is -40 ~ 40 o C, the reaction time is 4-24 h; the reaction is carried out under a protective atmosphere.

8. The method for preparing an aryl or heteroaryl trifluoromethyl tellurium ether compound according to claim 1, wherein: The first separation and purification method includes: column chromatography; wherein, The eluent used for the column chromatography is at least one of petroleum ether or ethyl acetate.

9. Use of trifluoromethyltellurium-modified aniracetam in the preparation of anticancer drugs; wherein: The structural formula of trifluoromethyltellurium-modified aniracetam is as follows: 。

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