Synthesis method and application of beta-fluorosulfonyl sulfone compounds
By generating alkyl radicals through photo-oxidation-reduction catalysis, the high difficulty in synthesizing β-fluorosulfonyl sulfone compounds in existing technologies has been solved, achieving efficient synthesis and diversified products, which are applicable to organic synthesis, drug development and polymer materials.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- ZHEJIANG NORMAL UNIV
- Filing Date
- 2026-03-04
- Publication Date
- 2026-06-05
AI Technical Summary
Existing technologies for synthesizing β-fluorosulfonyl sulfone compounds rely on a limited variety of raw materials and are difficult to synthesize, making it hard to meet the demand for structurally diverse intermediates in various applications.
Potassium trifluoroborate compounds were used as free radical precursors, combined with a photocatalyst, a sulfur dioxide source, and a hydrogen source, to carry out photo-oxidation-reduction catalysis under light irradiation to generate alkyl free radicals. Sulfonyl fluoride groups were then efficiently introduced at the β-position of the sulfone group through a free radical addition reaction.
This provides an efficient and simple synthetic route with high yield. The sulfonyl fluoride group has good potential for subsequent transformation and is suitable for organic synthesis, drug development and polymer materials.
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Figure CN122145356A_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the fields of chemical synthesis and medicinal chemistry, and particularly relates to a method for synthesizing β-fluorosulfonyl sulfone compounds and their applications. Background Technology
[0002] Sulfonyl fluorides, as core functional groups in next-generation click chemistry reactions, have demonstrated irreplaceable application value in various fields such as organic synthesis, materials science, and pharmaceutical research and development, becoming a research hotspot in the field of chemistry in recent years. Therefore, developing simple, efficient, and widely applicable synthetic methods for multifunctional sulfonyl fluoride compounds has significant academic research value and practical application prospects.
[0003] On the other hand, sulfones are a key class of organic synthesis intermediates, with their structures widely found in various drug molecules. They have broad applications in medicinal chemistry and materials science and possess rich biological activities. This makes multifunctionalized sulfones core intermediates in basic organic synthesis, drug development, and the production of life science-related products, and the innovation and optimization of their synthetic methods have attracted much attention.
[0004] Currently, the synthesis of sulfonyl fluoride compounds mainly relies on three strategies: in-situ construction of sulfonyl fluoride groups; modular synthesis based on sulfonyl fluoride building blocks; and direct fluorosulfonation reactions. In 2023, Qin Huali's research group (Org. Biomol. Chem., 2023, 21, 4967–4971 DOI: 10.1039 / d3ob00669g) reported a synthetic route that introduces sulfonyl fluoride groups at the β-position of the sulfone group through the direct reaction of sodium benzenesulfinate with ethylene sulfonyl fluoride (ESF). However, this strategy suffers from drawbacks such as the limited availability of raw materials and high synthetic difficulty, which significantly restricts the diversity of the target compound's structural framework and makes it difficult to meet the demand for structurally diverse intermediates in various applications. Therefore, there is an urgent need to develop a more universal synthetic method. Summary of the Invention
[0005] To address the aforementioned technical problems, this invention proposes a method for synthesizing β-fluorosulfonyl sulfone compounds and their applications.
[0006] To achieve the above objectives, the present invention provides the following technical solution: A method for synthesizing β-fluorosulfonyl sulfone compounds includes the following steps: Under a protective atmosphere, in an organic solvent, a potassium trifluoroborate compound, a photocatalyst, a sulfur dioxide source, a hydrogen source, and ethylene sulfonyl fluoride (ESF) are mixed and reacted under light irradiation to obtain the β-fluorosulfonyl sulfone compound; wherein the structure of the β-fluorosulfonyl sulfone compound is as follows: ; The general reaction formula is as follows: ; Wherein, R is selected from alkyl, substituted alkyl, alkenyl, alkoxy, ester, aryl, substituted aryl, heterocyclic or heterocyclic derivative groups.
[0007] Under photo-oxidation-reduction catalysis, potassium trifluoroborate is used as an alkyl radical precursor to generate alkyl radicals via photoinduced single-electron transfer. Subsequently, the radicals capture sulfur dioxide to form alkyl sulfonyl radicals, which then undergo radical addition reactions with ethylene sulfonyl fluoride. Finally, through an electron transfer step, sulfonyl fluoride groups are efficiently and specifically introduced at the β-position of the sulfone group, thereby constructing β-fluorosulfonyl sulfone compounds.
[0008] Furthermore, the organic solvent is selected from dichloroethane (DCE), dichloromethane, acetonitrile (MeCN), isopropanol, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, or methanol.
[0009] Furthermore, the potassium trifluoroborate compound is selected from one or more of cyclopentane potassium trifluoroborate, cyclohexane potassium trifluoroborate, aryl potassium trifluoroborate, substituted aryl potassium trifluoroborate and alkyl potassium trifluoroborate, and potassium trifluoroborate containing heterocyclic groups or heterocyclic derivative groups.
[0010] Further, the photocatalyst is selected from Acid Red 87, 2,4,5,6-tetrakis(9-carbazolyl)-isophthalonitrile (4CzIPN), tris(2,2'-bipyridine)ruthenium di(hexafluorophosphate), fac-Ir(ppy)3, Ir[ppy]2(dtbbpy)PF6, Ir[dF(CF3)ppy]2(dtbbpy)PF6, 10-methyl-9-mesotrimethylyl acridine perchlorate (Mes-Acr-Me-ClO4), and 3,6'-di-tert-butyl-9-mesotrimethylyl-10-benzene One or more of the following: 1,0-tetrafluoroborate (Mes-(t-Bu)2-Acr-Ph-BF4), 9-m-methyl-10-methylacridin-10-hydroiodate (Mes-Acr-Me-I), 9-trimethyl-10-methylacridin-10-hexafluorophosphate (Mes-Acr-Me-PF6), 9-m-dimethyl-10-phenylacridin-10-hydrochloride (Mes-Acr-Ph-Cl), and 9-m-dimethyl-2,7-dimethyl-10-phenylacridin-10-tetrafluoroborate.
[0011] Furthermore, the sulfur dioxide source is 1,4-diazabicyclo[2.2.2]octane-1,4-dion-1,4-disulfinic acid (DABSO).
[0012] Furthermore, the hydrogen source is water.
[0013] Furthermore, the reaction conditions are as follows: LED light is used for irradiation with a wavelength of 455-460nm, the irradiation time is 6-48 hours, and the reaction temperature is room temperature.
[0014] Further, the molar ratio of the potassium trifluoroborate compound to the photocatalyst is 3:(0.02-0.1); the molar ratio of the potassium trifluoroborate compound to ethylene sulfonyl fluoride is 3:(1-2); and the molar ratio of the potassium trifluoroborate compound to the sulfur dioxide source is 1:(0.5-1).
[0015] The present invention also provides a β-fluorosulfonyl sulfone compound prepared by the above-described synthetic method.
[0016] This invention also provides the application of β-fluorosulfonyl sulfone compounds in organic synthesis, drug preparation, preparation of pharmaceutical intermediates, or preparation of polymer materials.
[0017] Compared with the prior art, the present invention has the following advantages and technical effects: This invention utilizes potassium trifluoroborate as a radical precursor. Under a protective atmosphere, with the combined action of a photocatalyst, sulfur dioxide source, hydrogen source, and ethylene sulfonyl fluoride, alkyl radicals are generated via photoredox catalysis under light irradiation. This leads to the efficient introduction of sulfonyl fluoride at the β-position of the sulfone group, successfully synthesizing β-fluorosulfonyl sulfones. The method provided by this invention exhibits high reaction yield and outstanding synthetic efficiency, and the sulfonyl fluoride group in the product demonstrates excellent potential for subsequent transformations, showcasing significant synthetic application value. This invention provides a novel synthetic route for constructing β-fluorosulfonyl sulfones. Given the widespread presence of sulfone and sulfonyl fluoride groups in drug molecules, this method is expected to play an important role in organic synthesis, drug development, and polymer materials. This reaction, based on a radical mechanism, requires only simple light irradiation for initiation and offers comprehensive advantages such as mild conditions, simple operation, low equipment requirements, and readily available and economical raw materials. Attached Figure Description
[0018] The accompanying drawings, which form part of this invention, are used to provide a further understanding of the invention. The illustrative embodiments of the invention and their descriptions are used to explain the invention and do not constitute an undue limitation of the invention. In the drawings: Figure 1 The 1H NMR spectrum of the product prepared in Example 1; Figure 2 The carbon NMR spectrum of the product prepared in Example 1; Figure 3 The NMR fluorine spectrum of the product prepared in Example 1; Figure 4The mass spectrum is that of the product prepared in Example 1. Detailed Implementation
[0019] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as a limitation of the present invention, but rather as a more detailed description of certain aspects, features, and embodiments of the present invention.
[0020] It should be understood that the terminology used in this invention is merely for describing particular embodiments and is not intended to limit the invention. Furthermore, with respect to numerical ranges in this invention, it should be understood that each intermediate value between the upper and lower limits of the range is also specifically disclosed. Every smaller range between any stated value or intermediate value within a stated range, and any other stated value or intermediate value within said range, is also included in this invention. The upper and lower limits of these smaller ranges may be independently included or excluded from the range.
[0021] Unless otherwise stated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While only preferred methods and materials have been described herein, any methods and materials similar or equivalent to those described herein may be used in the implementation or testing of this invention. All references to this specification are incorporated by way of citation to disclose and describe methods and / or materials associated with those references. In the event of any conflict with any incorporated reference, the content of this specification shall prevail.
[0022] Various modifications and variations can be made to the specific embodiments described in this specification without departing from the scope or spirit of the invention, as will be apparent to those skilled in the art. Other embodiments derived from this specification will also be apparent to those skilled in the art. This specification and embodiments are merely exemplary.
[0023] The terms “include,” “including,” “have,” “contain,” etc., used in this article are all open-ended terms, meaning that they include but are not limited to.
[0024] This invention provides a method for synthesizing β-fluorosulfonyl sulfone compounds, with the following general reaction formula: ; Wherein, R is selected from alkyl, substituted alkyl, alkenyl, alkoxy, ester, aryl, substituted aryl, heterocyclic or heterocyclic derivative groups; Specifically, the following steps are included: 1) Add the specified amount of potassium trifluoroborate compound (free radical precursor) to a dry Schrank reaction tube. 2) Place the reaction tube under a nitrogen protective atmosphere, and add the set amounts of photocatalyst, DABSO, ESF, hydrogen source (water) and organic solvent in sequence, ensuring that all reagents are thoroughly mixed; 3) Seal the reaction tube, place it in a room temperature environment, turn on the LED lamp with a wavelength of 455-460nm for irradiation, and start the stirring device at the same time to continue the reaction for 6-48 hours (adjust the specific reaction time according to the substrate type). 4) After the reaction is complete, add ethyl acetate to the reaction system for extraction. Repeat the extraction 2-3 times and combine all organic layers. 5) Wash the organic layer 2-3 times with saturated brine to remove impurity ions, and then dry the organic layer with anhydrous sodium sulfate (Na2SO4) for 1-2 hours; 6) Filter to remove anhydrous sodium sulfate, and concentrate the filtrate to obtain crude product; 7) The crude product was purified by column chromatography or preparative thin-layer chromatography, using a mixture of petroleum ether and ethyl acetate in a volume ratio of 2:1 as the eluent. The target fraction was collected and concentrated to obtain pure β-fluorosulfonyl sulfone compounds. 8) The proton NMR spectrum of the product was determined using a 400MHz or 600MHz NMR spectrometer. 1 H NMR, carbon spectrum ( 13 C NMR and fluorine spectrum (C NMR) 19 F NMR was used to record data such as chemical shift (δ) and coupling constant (J) to verify the product structure; high-resolution mass spectrometry (ESI or EI source) was used to determine the molecular weight of the product and compare it with the theoretical molecular weight of the target compound to confirm the purity and correctness of the product structure.
[0025] In some optional embodiments of the present invention, the organic solvent is selected from dichloroethane (DCE), dichloromethane, acetonitrile (MeCN), isopropanol, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, or methanol.
[0026] In some optional embodiments of the present invention, the potassium trifluoroborate compound is selected from one or more of cyclopentane potassium trifluoroborate, cyclohexane potassium trifluoroborate, aryl trifluoroborate, substituted aryl trifluoroborate and alkyl trifluoroborate, and potassium trifluoroborate containing heterocyclic groups or heterocyclic derivative groups.
[0027] In some optional embodiments of the present invention, the photocatalyst is selected from Acid Red 87, 2,4,5,6-tetrakis(9-carbazolyl)-isophthalonitrile (4CzIPN), tris(2,2'-bipyridine)ruthenium di(hexafluorophosphate), fac-Ir(ppy)3, Ir[ppy]2(dtbbpy)PF6, Ir[dF(CF3)ppy]2(dtbbpy)PF6, 10-methyl-9-mesotrimylacrylidine perchlorate (Mes-Acr-Me-ClO4), 3,6'-di-tert-butyl-9-mesotrimyl- One or more of 10-phenylacridine-10-tetrafluoroborate (Mes-(t-Bu)2-Acr-Ph-BF4), 9-m-methyl-10-methylacridine-10-hydroiodate (Mes-Acr-Me-I), 9-trimethyl-10-methylacridine-10-hexafluorophosphate (Mes-Acr-Me-PF6), 9-m-dimethyl-10-phenylacridine-10-hydrochloride (Mes−Acr−Ph-Cl), and 9-m-dimethyl-2,7-dimethyl-10-phenylacridine-10-tetrafluoroborate. Mes-Acr-Me-ClO4 is preferred.
[0028] In some preferred embodiments of the present invention, the sulfur dioxide source is 1,4-diazabicyclo[2.2.2]octane-1,4-dionthium-1,4-disulfinic acid (DABSO).
[0029] In some preferred embodiments of the present invention, the hydrogen source is water.
[0030] In some optional embodiments of the present invention, the molar ratio of potassium trifluoroborate compound to photocatalyst is 3:(0.02-0.1), preferably 3:0.05; the molar ratio of potassium trifluoroborate compound to ethylene sulfonyl fluoride is 3:(1-2), preferably 3:1; and the molar ratio of potassium trifluoroborate compound to sulfur dioxide source is 1:(0.5-1), preferably 1:1.
[0031] Unless otherwise specified, "room temperature" in this invention refers to 25±2℃.
[0032] All raw materials used in this invention were purchased from the market.
[0033] The technical solution of the present invention will be further illustrated by the following embodiments.
[0034] Example 1 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are as follows: 0.3 mmol of 1a was added to a dry Schrank reaction tube, followed by 0.005 mmol of Mes-Acr-Me-ClO4, 0.3 mmol of DABSO, 0.1 mmol of ESF, 0.5 mmol of water, and 5.0 mL of dichloroethane under a nitrogen atmosphere. The reaction mixture was stirred for 12 hours at room temperature under a blue LED lamp with a wavelength of 455-460 nm. The mixture was then extracted with ethyl acetate, the organic layers were combined, washed with saturated brine, dried over Na2SO4, filtered, and concentrated. The mixture was further purified on silica gel by column chromatography or preparative thin-layer chromatography, with petroleum ether and ethyl acetate in a volume ratio of 2:1, to obtain a white solid product 2a in 91% yield.
[0035] The proton spectrum of the product (see) Figure 1 ), carbon spectrum (see Figure 2 ), Fluorine spectrum (see Figure 3 ) and high-resolution mass spectrometry (see Figure 4 The data is as follows: 1 H NMR, 400 MHz, chloroform: d 3.90 (dt, J = 12.9, 4.5 Hz, 2H), 3.51–3.43 (m,2H), 2.15–2.06 (m, 4H), 1.90–1.82 (m, 2H), 1.77–1.68 (m, 2H). 13 C NMR, 101 MHz, chloroform: d 62.5, 45.0, 43.3 (d, J = 21.4 Hz), 26.8, 25.9. 19 F NMR, 377 MHz, chloroform: d 55.4. HRMS (ESI) m / z calcd. for C7H 13 FO4S2[M + Na] + 267.0131, found 267.0160. Examples 2-6 Same as Example 1, except that the catalyst was replaced with equimolar amounts of Mes-(t-Bu)2-Acr-Ph-BF4, 4CzIPN, Mes-Acr-Me-I, Mes-Acr-Me-PF6, and Mes-Acr-Ph-Cl, respectively, and the yields of the products obtained were 67%, 10%, 85%, 80%, and 83%, respectively.
[0036] Examples 7-13 Same as Example 1, except that the solvent dichloroethane was replaced in equimolar amounts with acetonitrile, 1,4-dioxane, N,N-dimethylformamide, dimethyl sulfoxide, methanol, dichloromethane, and isopropanol, respectively. The yields of the obtained products were 83%, 53%, 45%, 24%, 62%, 77%, and 52%, respectively.
[0037] Example 14 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are as follows: 0.3 mmol of 1b is added to a dry Schrank reaction tube, followed by 0.005 mmol of Mes-Acr-Me-ClO4, 0.3 mmol of DABSO, 0.1 mmol of ESF, 0.5 mmol of water, and 5.0 mL of dichloroethane under a nitrogen atmosphere. The reaction mixture is stirred for 12 hours at room temperature under a blue LED lamp with a wavelength of 455-460 nm. The mixture is then extracted with ethyl acetate, the organic layers are combined, washed with saturated brine, dried over Na2SO4, filtered, and concentrated. The mixture is further purified on silica gel by column chromatography or preparative thin-layer chromatography, using petroleum ether and ethyl acetate in a volume ratio of 2:1, yielding a white solid product in 92% yield.
[0038] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 3.89 (dt, J = 12.9, 4.5 Hz, 2H), 3.44–3.40 (m,2H), 3.00–2.90 (m, 1H), 2.23–2.19 (m, 2H), 2.01–1.96 (m, 2H), 1.79–1.75 (m,1H), 1.63–1.59 (m, 1H), 1.37–1.25 (m, 4H). 13 C NMR, 101 MHz, chloroform: d 62.7, 43.2 (d, J = 21.2 Hz), 43.0, 25.1, 24.9,24.8. 19 F NMR, 377 MHz, chloroform: d 55.4. HRMS (ESI) m / z calcd. for C8H15 FO4S2[M + Na] + 281.0288, found 281.0274. Example 15 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1c. The yield of the obtained product is 92%.
[0039] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 3.90 (dt, J = 12.8, 4.6 Hz, 2H), 3.51–3.47 (m,2H), 3.12–3.08 (m, 2H), 1.93–1.85 (m, 2H), 1.50–1.34 (m, 4H), 0.94 (t, J =7.1 Hz, 3H). 13 C NMR, 101 MHz, chloroform: d 54.3, 46.1, 43.4 (d, J = 21.5 Hz), 30.4, 22.1,21.7, 13.6. 19 F NMR, 377 MHz, chloroform: d 55.5. HRMS (ESI) m / z calcd. for C7H 15 FO4S2[M + Na] + 269.0288, found 269.0341. Example 16 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1d. The yield of the obtained product is 89%.
[0040] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 3.88 (dt,J = 12.7, 4.6 Hz, 2H), 3.50–3.46 (m,2H), 3.05 (s, 2H), 1.25 (s, 9H). 13 C NMR, 101 MHz, chloroform: d 65.5, 49.1, 43.4 (d, J = 21.6 Hz), 32.5, 29.7. 19 F NMR, 377 MHz, chloroform: d 55.6. HRMS (ESI) m / z calcd. for C7H 15 FO4S2[M + Na] + 269.0288, found 269.0341. Example 17 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1e. The yield of the obtained product is 84%.
[0041] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 600 MHz, chloroform: d 3.90 (dt, J = 12.6, 4.6 Hz, 2H), 3.49–3.46 (m,2H), 3.27 (dd, J = 14.0, 8.6 Hz, 1H), 3.18 (dd, J = 14.0, 4.9 Hz, 1H), 2.83–2.80 (m, 1H), 2.42–2.38 (m, 1H), 2.26–2.19 (m, 1H), 2.02–1.89 (m, 4H), 1.70–1.64 (m, 1H), 1.22 (s, 3H), 1.05 (d, J = 10.0 Hz, 1H), 1.02 (s, 3H). 13 C NMR, 151 MHz, chloroform: d61.7, 46.8 (d, J = 56.2 Hz), 43.4 (d, J = 21.3Hz), 40.5, 38.4, 34.4, 32.4, 27.5, 25.7, 23.1, 22.0. 19 F NMR, 565 MHz, chloroform: d 55.4. HRMS (ESI) m / z calcd. for C 12 H 21 FO4S2[M + Na] + 335.0757, found 335.0783. Example 18 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1f. The yield of the obtained product is 61%.
[0042] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 5.16 (s, 2H), 4.54–4.48 (m, 2H), 3.96–3.92 (m, 2H). 13 C NMR, 101 MHz, dimethyl sulfoxide: d 43.9, 43.5 (d, J = 17.7 Hz), 42.5. 19 F NMR, 377 MHz, dimethyl sulfoxide: d 55.9. Example 19 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1g. The yield of the obtained product is 76%.
[0043] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d4.51 (s, 2H), 3.91 (dt, J = 12.9, 4.7 Hz, 2H), 3.57–3.53 (m, 2H), 1.31 (s, 9H). 13 C NMR, 101 MHz, chloroform: d 78.8, 78.7, 44.5, 44.2 (d, J = 21.1 Hz), 27.4. 19 F NMR, 377 MHz, chloroform: d 54.8. HRMS (ESI) m / z calcd. for C7H 15 FO5S2[M + Na] + 285.0237, found 285.0209. Example 20 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1h. The yield of the obtained product is 74%.
[0044] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 5.88–5.78 (m, 1H), 5.25–5.19 (m, 2H), 3.90(dt, J = 12.5, 4.5 Hz, 2H), 3.52–3.49 (m, 2H), 3.22–3.18 (m, 2H), 2.68–2.62 (m,2H). 13 C NMR, 101 MHz, chloroform: d 132.9, 118.5, 53.4, 46.7, 43.4 (d, J = 21.5Hz), 26.2. 19 F NMR, 377 MHz, chloroform: d 55.6. Example 21 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1i, and the irradiation and stirring time is 48 hours. The yield of the obtained product is 56%.
[0045] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 4.45–4.40 (m, 2H), 3.83–3.79 (m, 2H), 3.65 (s, 3H), 3.58 (t, J = 7.3 Hz, 2H), 2.83 (t, J = 7.3 Hz, 2H). 13 C NMR, 101 MHz, dimethyl sulfoxide: d 170.8, 52.1, 48.1, 45.8, 43.6 (d, J =17.5 Hz), 26.4. 19 F NMR, 377 MHz, dimethyl sulfoxide: d 55.8. HRMS (ESI) m / z calcd. for C6H 11 FO6S2[M + K] + 300.9613, found 300.9667. Example 22 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1j. The yield of the obtained product is 89%.
[0046] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 3.91 (dt, J = 12.9, 4.6 Hz, 2H), 3.47–3.43 (m,2H), 3.28–3.18 (m, 1H), 1.47 (d, J = 6.9 Hz, 6H). 13 C NMR, 101 MHz, chloroform: d54.8, 43.2 (d, J = 21.4 Hz), 42.8, 15.3. 19 F NMR, 377 MHz, chloroform: d 55.4. HRMS (ESI) m / z calcd. for C5H 11 FO4S2[M + Na] + 240.9975, found 240.9992. Example 23 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1k. The yield of the obtained product is 95%.
[0047] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 3.94–3.89(m, 2H), 3.45–3.41 (m, 2H), 1.48 (s,9H). 13 C NMR, 101 MHz, chloroform: d 60.4, 43.2 (d, J = 21.3 Hz), 39.9, 23.3. 19 F NMR, 377 MHz, chloroform: d 55.5. HRMS (ESI) m / z calcd. for C6H 13 FO4S2[M + Na] + 255.0131, found 255.0128. Example 24 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1l. The yield of the obtained product is 63%.
[0048] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 7.35–7.30 (m, 4H), 7.27–7.22 (m, 1H), 4.48–4.42 (m, 2H), 3.76–3.72 (m, 2H), 3.64–3.61 (m, 2H), 3.06–3.02 (m, 2H). 13 C NMR, 101 MHz, dimethyl sulfoxide: d 138.0, 128.7, 128.6, 126.8, 53.0, 45.8,43.7 (d, J = 17.4 Hz), 26.8. 19 F NMR, 377 MHz, dimethyl sulfoxide: d 55.7. HRMS (ESI) m / z calcd. for C 10 H 13 FO4S2[M + Na] + 303.0131, found 303.0167. Example 25 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1m. The yield of the obtained product is 58%.
[0049] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 600 MHz, chloroform: d 7.35 (t, J = 7.6 Hz, 4H), 7.31–7.26 (m, 6H), 4.66 (t, J = 7.4 Hz, 1H), 3.83 (d, J = 7.4 Hz, 2H), 3.56 (dt, J = 12.8, 4.7 Hz, 2H), 2.76–2.73 (m, 2H). 13 C NMR, 151 MHz, chloroform: d140.7, 129.3, 127.8, 127.5, 60.2, 47.3, 45.8,43.3 (d, J = 21.0 Hz). 19 F NMR, 565 MHz, chloroform: d 55.0. HRMS (ESI) m / z calcd. for C 16 H 17 FO4S2[M + Na] + 379.0444, found 379.0458. Example 26 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1n, and the equimolar amount of solvent dichloroethane is replaced with acetonitrile. The yield of the obtained product is 60%.
[0050] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 7.95 (d, J = 7.6 Hz, 2H), 7.77 (t, J = 7.5 Hz, 1H), 7.66 (t, J = 7.8 Hz, 2H), 3.80 (dt, J = 12.5, 4.5 Hz, 2H), 3.61–3.57 (m,2H). 13 C NMR, 101 MHz, chloroform: d 137.5, 135.0, 130.0, 128.2, 49.8, 44.4 (d, J =21.3 Hz). 19 F NMR, 377 MHz, chloroform: d 55.5. Example 27 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1o. The yield of the obtained product is 88%.
[0051] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 7.81 (d, J = 7.9 Hz, 2H), 7.44 (d, J = 7.9 Hz, 2H), 3.78 (dt, J = 12.8, 4.5 Hz, 2H), 3.59–3.54 (m, 2H), 2.49 (s, 3H). 13 C NMR, 101 MHz, chloroform: d 146.4, 134.5, 130.5, 128.2, 49.8, 44.5 (d, J =21.2 Hz), 21.7. 19 F NMR, 377 MHz, chloroform: d 55.4. HRMS (ESI) m / z calcd. for C9H 11 FO4S2[M + Na] + 288.9975, found 288.9958. Example 28 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1p. The yield of the obtained product is 70%.
[0052] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 600 MHz, chloroform: d 8.00–7.98 (m, 1H), 7.62–7.60 (m, 1H), 7.46–7.41 (m, 2H), 3.82–3.78 (m, 2H), 3.63–3.60 (m, 2H), 2.72 (s, 3H). 13C NMR, 151 MHz, chloroform: d 138.3, 135.5, 134.9, 133.3, 130.3, 127.1,48.7, 44.2 (d, J = 21.0 Hz), 20.3. 19 F NMR, 377 MHz, chloroform: d 55.5. HRMS (ESI) m / z calcd. for C9H 11 FO4S2[M + Na] + 288.9975, found 288.9958. Example 29 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1q. The yield of the obtained product is 71%.
[0053] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 600 MHz, chloroform: d 7.73 (d, J = 7.0 Hz, 2H), 7.56–7.51 (m, 2H), 3.81 – 3.78 (m, 2H), 3.60–3.57 (m, 2H), 2.49 (s, 3H). 13 C NMR, 151 MHz, chloroform: d 140.5, 137.3, 135.8, 129.7, 128.3, 125.2,49.7, 44.4 (d, J = 21.0 Hz), 21.3. 19 F NMR, 565 MHz, chloroform: d 55.3. HRMS (ESI) m / z calcd. for C9H 11 FO4S2[M + Na] + 288.9975, found 288.9958. Example 30 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1r. The yield of the obtained product is 75%.
[0054] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 600 MHz, chloroform: d 7.67–7.64 (m, 2H), 7.38 (d, J = 7.9 Hz, 1H), 3.79–3.75 (m, 2H), 3.58–3.55 (m, 2H), 2.38 (s, 3H), 2.37 (s, 3H). 13 C NMR, 151 MHz, chloroform: d 145.0, 139.0, 134.5, 130.9, 128.7, 125.6,49.7, 44.5 (d, J = 21.0 Hz), 20.1, 19.9. 19 F NMR, 565 MHz, chloroform: d 55.2. HRMS (ESI) m / z calcd. for C 10 H 13 FO4S2[M + Na] + 303.0131, found 303.0167. Example 31 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1s. The yield of the obtained product is 60%.
[0055] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: 7.85 (d, J = 8.5 Hz, 2H), 7.64 (d, J= 8.5 Hz, 2H), 3.82–3.77 (m, 2H), 3.60–3.55 (m, 2H), 1.37 (s, 9H). 13 C NMR, 101 MHz, chloroform: d 159.3, 134.4, 128.1, 127.0, 49.8, 44.5 (d, J =21.1 Hz), 35.5, 31.0. 19 F NMR, 377 MHz, chloroform: d 55.5. HRMS (ESI) m / z calcd. for C 12 H 17 FO4S2[M + Na] + 331.0445, found 331.0444. Example 32 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1t, and the equimolar amount of solvent dichloroethane is replaced with acetonitrile. The yield of the obtained product is 63%.
[0056] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 7.88–7.84 (m, 2H), 7.10–7.06 (m, 2H), 3.92 (s,3H), 3.81–3.75 (m, 2H), 3.58–3.54 (m, 2H). 13 C NMR, 101 MHz, chloroform: d 164.7, 130.4, 128.7, 115.1, 55.9, 50.0, 44.6(d, J = 20.8 Hz). 19 F NMR, 377 MHz, chloroform: d 55.4. Example 33 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1u. The yield of the obtained product is 48%.
[0057] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 8.08–8.05(m, 2H), 7.57–7.53 (t, J = 8.7Hz, 2H), 4.34–4.28 (m, 2H), 4.00–3.96 (m, 2H). 13 C NMR, 101 MHz, dimethyl sulfoxide: d 165.6 (d, J = 253.3 Hz), 134.2 (d, J = 2.8Hz), 131.7 (d, J = 10.1 Hz), 117.0 (d, J = 22.9 Hz), 48.6, 44.1 (d, J = 17.5 Hz). 19 F NMR, 377 MHz, dimethyl sulfoxide: d 56.3, -103.9. Example 34 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1v, and the equimolar amount of solvent dichloroethane is replaced with acetonitrile. The yield of the obtained product is 50%.
[0058] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 8.00 (d, J = 8.5 Hz, 2H), 7.78 (d, J = 8.3Hz, 2H), 4.34–4.29 (m, 2H), 4.02–3.98 (m, 2H). 13C NMR, 101 MHz, dimethyl sulfoxide: d 139.8, 136.7, 130.4, 129.8, 48.5, 44.1(d, J = 17.6 Hz). 19 F NMR, 377 MHz, dimethyl sulfoxide: d 56.3. Example 35 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1w, and the equimolar amount of solvent dichloroethane is replaced with acetonitrile. The yield of the obtained product is 54%.
[0059] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 7.94–7.89 (m, 4H), 4.34–4.29 (m, 2H), 4.01 –3.97 (m, 2H). 13 C NMR, 101 MHz, dimethyl sulfoxide: d 137.1, 132.8, 130.4, 129.0, 48.5, 44.0(d, J = 17.6 Hz). 19 F NMR, 377 MHz, dimethyl sulfoxide: d 56.3. Example 36 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1x, the equimolar amount of solvent dichloroethane is replaced with acetonitrile, and the irradiation and stirring time is 48 hours. The yield of the obtained product is 35%.
[0060] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 8.06 (d, J = 8.4 Hz, 1H), 7.99 (d,J = 8.3Hz, 1H), 7.79 (d, J = 7.6 Hz, 1H), 7.54 (t, J = 7.3 Hz, 1H), 7.49 (d, J = 7.2 Hz,1H), 4.37– 4.32 (m, 2H), 4.01–3.98 (m, 2H). 13 C NMR, 101 MHz, dimethyl sulfoxide: d 146.0, 138.3, 136.6, 129.3, 129.0,127.8, 127.3, 126.0, 48.6, 44.2 (d, J = 17.5 Hz). 19 F NMR, 377 MHz, dimethyl sulfoxide: d 56.3. Example 37 A method for synthesizing β-fluorosulfonyl sulfone compounds, the synthetic route is as follows: The specific steps are the same as in Example 1, except that the equimolar amount of reactant 1a is replaced with 1y, the equimolar amount of solvent dichloroethane is replaced with acetonitrile, and the irradiation and stirring time is 48 hours. The yield of the obtained product is 28%.
[0061] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 1H NMR, 400 MHz, dimethyl sulfoxide: d 8.66 (d, J = 1.9 Hz, 1H), 8.24–8.21 (m,2H), 8.12 (d, J = 8.4 Hz, 1H), 7.81 (dd, J = 8.7, 2.0 Hz, 1H), 7.81–7.71(m, 2H), 4.37– 4.32 (m, 2H), 4.04–4.00 (m, 2H). 13 C NMR, 101 MHz, dimethyl sulfoxide: d135.2, 134.9, 131.8, 130.3, 129.8,129.8, 129.8, 128.0, 127.9, 122.8, 48.6, 44.2 (d, J = 17.5 Hz). 19 F NMR, 377 MHz, dimethyl sulfoxide: d 56.2. Application Example 1 The 2a obtained in Example 1 was used as a reactant to further prepare other products. The synthetic route is as follows: The specific steps are as follows: 0.2 mmol of 2a, 0.4 mmol of sodium hydroxide, and 1.0 mL of water were added to a dry Schrank reaction tube. The reaction mixture was stirred at 40 °C for 1 hour. Then, the mixture was extracted with ethyl acetate, the organic layer was discarded, the aqueous phase was evaporated to dryness, the obtained solid was dissolved in a mixture of hot water and ethanol, the insoluble matter was filtered off, the filtrate was cooled at -20 °C, the precipitated solid was collected by filtration and dried, and a white solid product 4 was obtained in 82% yield.
[0062] The proton, carbon, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, deuterium in water: d 3.85–3.77(m, 1H), 3.63–3.59 (m, 2H), 3.39–3.35(m, 2H), 2.18 – 2.01 (m, 2H), 2.06–1.97 (m, 2H), 1.84–1.70 (m, 4H). 13 C NMR, 101 MHz, deuterium in water: d 61.1, 46.6, 42.9, 26.2, 25.7. Application Example 2 The 2a obtained in Example 1 was used as a reactant to further prepare other products. The synthetic route is as follows: The specific steps are as follows: 0.2 mmol of 2a is added to a dry Schrank reaction tube, followed by 0.4 mmol of morpholine, 0.4 mmol of triethylamine, and 2.0 mL of acetonitrile under a nitrogen atmosphere. The reaction mixture is stirred at 80 °C for 24 hours. The mixture is then extracted with ethyl acetate, the organic layers are combined, washed with saturated brine, dried over Na2SO4, filtered, and concentrated. The mixture is further purified on silica gel by column chromatography or preparative thin-layer chromatography, using petroleum ether and ethyl acetate in a volume ratio of 2:1. A white solid product 5 is obtained in 92% yield.
[0063] The proton, carbon, fluorine, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 400 MHz, chloroform: d 3.78–3.77 (m, 4H), 3.52–3.46 (m, 1H), 3.43–3.36 (m, 4H), 3.32–3.30 (m, 4H), 2.09–2.06 (m, 4H), 1.86–1.81 (m, 2H), 1.72–1.68 (m, 2H). 13 C NMR, 101 MHz, chloroform: d 66.3, 62.12, 62.07, 45.6, 44.8, 43.2,40.6, 26.7, 26.6, 25.8, 25.8. HRMS (ESI) m / z calcd. for C 11 H 21 NO5S2[M + Na] + 334.0753, found 334.0757. Application Example 3 The 2a obtained in Example 1 was used as a reactant to further prepare other products. The synthetic route is as follows: The specific steps are as follows: 0.2 mmol of 2a is added to a dry Schrank reaction tube, followed by 0.4 mmol of 2-naphthol, 0.4 mmol of potassium carbonate, and 4.0 mL of acetonitrile under a nitrogen atmosphere. The reaction mixture is stirred at room temperature for 12 hours. The mixture is then extracted with ethyl acetate, the organic layers are combined, washed with saturated brine, dried over Na2SO4, filtered, and concentrated. The mixture is further purified on silica gel by column chromatography or preparative thin-layer chromatography, using petroleum ether and ethyl acetate in a volume ratio of 2:1, to obtain a white solid product in 65% yield.
[0064] The proton, carbon, and high-resolution mass spectrometry data of the product are as follows: 1 H NMR, 600 MHz, chloroform: d 7.90 (d, J = 8.9 Hz, 1H), 7.88–7.83 (m,2H),7.76 (d, J = 2.4 Hz, 1H), 7.56–7.52 (m, 2H), 7.38 (dd, J = 9.0, 2.5 Hz, 1H),3.82–3.79 (m, 2H), 3.55–3.52 (m, 2H), 3.48–3.43 (m, 1H), 2.13–2.02 (m, 4H), 1.86–1.78 (m, 2H), 1.71–1.64 (m, 2H). 13 C NMR, 101 MHz, chloroform: d 146.3, 133.5, 132.1, 130.5, 127.9, 127.8, 127.3, 126.8, 120.4, 119.4, 62.2, 45.4, 42.7, 26.7, 25.9. HRMS (ESI) m / z calcd. for C 17 H 20 O5S2[M + Na] + 391.0644, found 391.0654. Application Example 4 The 2a obtained in Example 1 was used as a reactant to further prepare other products. The synthetic route is as follows: The specific steps are as follows: 0.2 mmol of 2a was added to a dry Schrank reaction tube, followed by 0.24 mmol of p-hydroxyanisole, 0.24 mmol of potassium carbonate, and 1.0 mL of acetonitrile under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 12 hours; then extracted with ethyl acetate, the organic layers were combined, washed with saturated brine, dried over Na2SO4, filtered, and concentrated. Further purification was performed on silica gel by column chromatography or preparative thin-layer chromatography, using petroleum ether and ethyl acetate in a 2:1 volume ratio as eluent, yielding a white solid product in 68% yield.
[0065] The proton, carbon, and high-resolution mass spectrometry data of the product are as follows: 1H NMR, 600 MHz, chloroform: d7.21–7.19 (m, 2H), 6.93–6.91 (m, 2H), 3.81(s,3H), 3.73–3.69 (m, 2H), 3.51–3.42 (m, 3H), 2.14–2.02 (m, 4H), 1.86–1.80 (m,2H), 1.75–1.65 (m,2H). 13C NMR, 101 MHz, chloroform: δ 158.7, 142.1, 122.9, 115.0, 62.2, 55.6, 45.4, 42.2, 26.7, 25.9. HRMS (ESI) m / z calcd. for C 14 H 20 O6S2[M + Na] + 371.0594, found 371.0607. The above are merely preferred embodiments of the present invention, but the scope of protection of the present invention is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the scope of the technology disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.
Claims
1. A method for synthesizing β-fluorosulfonyl sulfone compounds, characterized in that, Includes the following steps: Under a protective atmosphere, potassium trifluoroborate, a photocatalyst, a sulfur dioxide source, a hydrogen source, and ethylene sulfonyl fluoride are mixed in an organic solvent and reacted under light irradiation to obtain the β-fluorosulfonyl sulfone compound; wherein the structure of the β-fluorosulfonyl sulfone compound is as follows: ； Wherein, R is selected from alkyl, substituted alkyl, alkenyl, alkoxy, ester, aryl, substituted aryl, heterocyclic or heterocyclic derivative groups.
2. The method for synthesizing β-fluorosulfonyl sulfone compounds according to claim 1, characterized in that, The organic solvent is selected from dichloroethane, dichloromethane, acetonitrile, isopropanol, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, or methanol.
3. The method for synthesizing β-fluorosulfonyl sulfone compounds according to claim 1, characterized in that, The potassium trifluoroborate compounds are selected from one or more of cyclopentane potassium trifluoroborate, cyclohexane potassium trifluoroborate, aryl trifluoroborate, substituted aryl trifluoroborate, alkyl potassium trifluoroborate, and potassium trifluoroborate containing heterocyclic groups or heterocyclic derivative groups.
4. The method for synthesizing β-fluorosulfonyl sulfone compounds according to claim 1, characterized in that, The photocatalyst is selected from Acid Red 87, 2,4,5,6-tetrakis(9-carbazolyl)-isophthalonitrile, tris(2,2'-bipyridine)ruthenium di(hexafluorophosphate), fac-Ir(ppy)3, Ir[ppy]2(dtbbpy)PF6, Ir[dF(CF3)ppy]2(dtbbpy)PF6, 10-methyl-9-trimethylylacrimidine perchlorate, 3, One or more of the following: 6,-di-tert-butyl-9-trimethyl-10-phenylacridine-10-tetrafluoroborate, 9-m-methyl-10-methylacridine-10-hydroiodate, 9-trimethyl-10-methylacridine-10-hexafluorophosphate, 9-m-dimethyl-10-phenylacridine-10-hydrochloride, and 9-m-dimethyl-2,7-dimethyl-10-phenylacridine-10-tetrafluoroborate.
5. The method for synthesizing β-fluorosulfonyl sulfone compounds according to claim 1, characterized in that, The sulfur dioxide source is 1,4-diazabicyclo[2.2.2]octane-1,4-diaonium-1,4-disulfinic acid.
6. The method for synthesizing β-fluorosulfonyl sulfone compounds according to claim 1, characterized in that, The hydrogen source is water.
7. The method for synthesizing β-fluorosulfonyl sulfone compounds according to claim 1, characterized in that, The reaction conditions are as follows: LED light is used for irradiation with a wavelength of 455-460nm, the irradiation time is 6-48 hours, and the reaction temperature is room temperature.
8. The method for synthesizing β-fluorosulfonyl sulfone compounds according to claim 1, characterized in that, The molar ratio of potassium trifluoroborate compound to photocatalyst is 3:(0.02-0.1); the molar ratio of potassium trifluoroborate compound to ethylene sulfonyl fluoride is 3:(1-2); and the molar ratio of potassium trifluoroborate compound to sulfur dioxide source is 1:(0.5-1).
9. The use of a β-fluorosulfonyl sulfone compound prepared by the method according to any one of claims 1-8 in organic synthesis, drug preparation, preparation of pharmaceutical intermediates or preparation of polymer materials.