CN110698369B - Method for synthesizing aryl acetylene alkyl sulfone compound based on alkyl fluoborate - Google Patents
Method for synthesizing aryl acetylene alkyl sulfone compound based on alkyl fluoborate Download PDFInfo
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Abstract
The invention belongs to the technical field of organic chemistry, and particularly relates to a method for synthesizing aryl acetylene alkyl sulfone compounds based on alkyl fluoborate. The method for synthesizing the aryl acetylene alkyl sulfone compound provided by the invention is to use 9-mesityl-10-methylacridine perchlorate (Mes-Acr) as a photosensitizer under the condition of visible light+ClO4 ‑674783-97-2), then a photosensitizer acts on the potassium alkyl fluoborate to obtain an alkyl radical, the alkyl radical is combined with sulfur dioxide to generate an alkyl sulfonyl radical, and the alkyl sulfonyl radical and aryl acetylene bromide are added to obtain a series of aryl acetylene alkyl sulfone compounds. The preparation method of the aryl acetylene alkyl sulfone compound has the advantages of mild conditions, simplicity, high efficiency, high reaction yield, good product purity, convenience for separation and purification and good application value.
Description
Technical Field
The invention belongs to the technical field of organic chemistry, and particularly relates to a method for synthesizing aryl acetylene alkyl sulfone compounds based on alkyl fluoborate.
Background
The sulfonyl compounds have good biological activity and are widely present in drug molecules. The traditional method for synthesizing the compounds often needs to use sulfonation reagents with high toxicity and strong corrosiveness, so that the development of a novel, efficient, economical and green sulfonylation method for constructing sulfonyl fragments is a key direction of research of chemists. In recent years, there have been increasing reports of sulfonylation reactions using sulfur dioxide substitutes, such as sodium metabisulfite, potassium metabisulfite, DABSO or sodium formaldehyde sulfoxylate as indirect sulfonation reagents. In the reaction, the reaction is green and efficient, so that the harsh conditions of strong acid or strong oxidation in the traditional synthesis are avoided, and chemists continuously explore a synthesis method for carrying out sulfonylation by using the sulfur dioxide substitute.
Among a plurality of synthetic methods, the free radical series reaction has the advantages of simple operation, economy, high efficiency, mild conditions and the like, and is widely applied to the field of organic synthesis. The photochemical reaction which has been favored for decades is a simple, efficient, clean organic synthesis strategy. In the reaction system, visible light is utilized to absorb photon excitation on the photosensitizer, so that the photosensitizer generates a specific oxidation or reduction state, and the photosensitizer and a reaction substrate can carry out single electron transfer to initiate a free radical reaction.
Based on the above, the invention aims to provide a method for synthesizing aryl acetylene alkyl sulfone compounds by catalyzing the reaction among three components, namely aryl acetylene bromide, alkyl fluoborate and a sulfur dioxide solid substitute by using a photosensitizer under the condition of visible light.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provides a method for synthesizing aryl acetylene alkyl sulfone compounds based on alkyl fluoborate.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a method for synthesizing aryl acetylene alkyl sulfone compounds based on alkyl fluoborate, which comprises the following steps of in a solvent, under the condition of visible light, acting a photosensitizer on the alkyl fluoborate to generate alkyl free radicals, then combining the alkyl free radicals with sulfur dioxide to generate alkyl sulfonyl free radicals, and then adding the alkyl sulfonyl free radicals and aryl acetylene bromine to obtain the aryl acetylene alkyl sulfone compounds, wherein the method comprises the following steps:
(1) at room temperature, adding aryl acetylene bromide, a sulfur dioxide solid substitute, alkyl fluoborate, ammonium fluoride and a photosensitizer into a reaction tube according to a certain molar ratio, placing the reaction tube in a protective atmosphere to fully replace gas, adding a solvent, and reacting under the condition of visible light;
(2) and after the reaction is completed, concentrating the reaction liquid, and performing column chromatography separation on the concentrated reaction liquid to obtain the aryl acetylene alkyl sulfone compound.
Preferably, the alkyl fluoroborate described in the present invention includes potassium alkyl fluoroborate.
Preferably, the alkyl group of the alkyl fluoroborate described in the present invention includes ethyl, propyl, tert-butyl, cyclopentyl and cyclohexyl.
Preferably, the aryl group of the arylacetylene bromide in the present invention is an aryl group having an electron withdrawing group including fluorine, chlorine, bromine and trifluoromethyl or an electron donating group including alkyl, methoxy and phenyl.
Preferably, the photosensitizers described in the present invention include Mes-Acr+ClO4 -(9-mesityl-10-methylacridine perchlorate, CAS:674783-97-2) and other oxidative photosensitizers including acid Red 87 and 4 CzIPN; a more preferred photosensitizer is Mes-Acr+ClO4 -。
Preferably, the sulfur dioxide solid substitute described in the present invention comprises sodium metabisulfite (Na)2S2O5) Potassium metabisulfite (K)2S2O5) And DABCO.(SO2)2(DABSO)。
Preferably, the molar ratio of the aryl acetylene bromide, the sulfur dioxide solid substitute, the alkyl fluoborate, the ammonium fluoride and the photosensitizer in the step (1) is 1: (1.5-2.5): (1.0-2.0): (1.0-3.0): (0.05-0.25), more preferably 1: 2.0: 1.5: 2.0: 0.1.
preferably, the protective atmosphere in step (1) comprises nitrogen and argon, and more preferably, the protective atmosphere is high-purity nitrogen or argon (high purity > 99.999%).
Preferably, the sufficient replacement gas described in step (1) is such that the reaction system is in an oxygen-free environment.
Preferably, the solvent in step (1) is an organic solvent comprising acetonitrile and 1, 2-dichloroethane, more preferably acetonitrile; the amount of the solvent is a usual amount for allowing the reaction to proceed uniformly, and in the present invention, it is preferably 2.0 mL.
Preferably, the visible light in step (1) is a 35W fluorescent lamp, and the reaction is preferably carried out under stirring conditions.
Preferably, the monitoring method for the completion of the reaction in the step (2) is TLC monitoring, and the reaction time is preferably 48 h.
Preferably, the reaction solution is concentrated under reduced pressure in the step (2).
Preferably, the solvent used for column chromatography separation in step (2) is a common separation solvent system, and comprises a mixed solution of petroleum ether and ethyl acetate.
The preferred reaction formula of the present invention is as follows:
compared with the prior art, the invention has the following beneficial effects: the invention provides a method for synthesizing aryl acetylene alkyl sulfone compounds based on alkyl fluoborate, which comprises the steps of utilizing a photosensitizer to act on the alkyl fluoborate under the irradiation of visible light to obtain alkyl free radicals under very mild and simple conditions, then combining the alkyl free radicals with sulfur dioxide to generate alkyl sulfonyl free radicals, carrying out addition reaction on the alkyl sulfonyl free radicals and aryl acetylene bromide, and leaving bromide anions to obtain a target product. The method has the advantages of simple raw material preparation and mild reaction conditions, and provides a simple, convenient and efficient synthetic method for constructing a series of aryl acetylene alkyl sulfone compounds. The method avoids harsh conditions in the synthesis of the traditional sulfonyl compounds, can be used for large-scale industrial preparation, and has good guiding significance and application prospect in the fields of scientific research and industry.
Detailed Description
The method for synthesizing aryl acetylene alkyl sulfones based on alkyl fluoroborate provided by the invention is described in detail with reference to the following specific examples, and it is obvious that the described examples are only a part of the examples of the invention, but not all the examples. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
0.2mmol of phenylacetylene bromide, 0.4mmol of sodium metabisulfite, 0.3mmol of cyclopentyl potassium fluoroborate, 0.4mmol of ammonium fluoride and 2.0 mmol% of Mes-Acr are sequentially added into a reaction tube+ClO4 -The reaction tube is plugged with a rubber plug and placed in high-purity nitrogen for ventilation, 2.0mL of acetonitrile is added after the system is in an anaerobic condition, and the mixture is stirred and reacts under the irradiation of a 35W fluorescent lamp. After 48 hours of reaction, the reaction solution is directly concentrated under reduced pressure, column chromatography separation is carried out, and a mixed solution of petroleum ether and ethyl acetate is used as a mobile phase, so that the compound example 1 can be obtained. The yield was 74%.
Structural characterization of compound example 1:
1H NMR(400MHz,CDCl3)：δ7.58(d,J＝7.2Hz,2H),7.52(m,1H),7.42(m,2H),3.87–3.59(m,1H),2.44–2.07(m,4H),1.79(m,4H).13C NMR(101MHz,CDCl3)：δ32.7,131.5,128.7,117.7,92.6,82.5,66.1,27.3,26.0.HRMS(ESI)calcd for C13H14O2S+:235.0787(M+H+),found:235.0781.
example 2:
0.2mmol of phenylacetylene bromide, 0.3mmol of potassium metabisulfite, 0.2mmol of potassium ethylfluoroborate, 0.2mmol of ammonium fluoride and 1.0 mmol% of Mes-Acr are sequentially added into a reaction tube+ClO4 -The reaction tube is plugged with a rubber plug and placed in high-purity nitrogen for ventilation, 2.0mL of 1, 2-dichloroethane is added after the system is in an anaerobic condition, and the reaction is stirred under the irradiation of a 35W fluorescent lamp. After 48 hours of reaction, the reaction liquid is directly decompressed and concentrated, and is separated by column chromatography, and stone is adoptedThe compound example 2 was obtained using a mixed solution of oleyl ether and ethyl acetate as a mobile phase. The yield was 50%.
Structural characterization of compound example 2:
1H NMR(400MHz,CDCl3)：δ7.60(d,J＝7.4Hz,2H),7.52(m,1H),7.43(m,2H),3.31(d,J＝7.3Hz,2H),1.54(t,J＝7.3Hz,3H).13C NMR(101MHz,CDCl3)：δ132.8,131.6,128.7,117.5,92.4,82.6,52.7,7.6.HRMS(ESI)calcd for C10H10O2S+:195.0474(M+H+),found:195.0475.
example 3:
0.2mmol of phenylacetylene bromide, 0.5mmol of sodium metabisulfite, 0.4mmol of potassium tert-butylfluoroborate, 0.6mmol of ammonium fluoride and 5.0 mmol% of Mes-Acr were sequentially added to a reaction tube+ClO4 -The reaction tube is plugged with a rubber plug and placed in high-purity nitrogen for ventilation, 2.0mL of acetonitrile is added after the system is in an anaerobic condition, and the mixture is stirred and reacts under the irradiation of a 35W fluorescent lamp. After 48 hours of reaction, the reaction solution is directly concentrated under reduced pressure, column chromatography separation is carried out, and a mixed solution of petroleum ether and ethyl acetate is used as a mobile phase, so that the compound example 3 can be obtained. The yield was 75%.
Structural characterization of compound example 3:
1H NMR(400MHz,CDCl3)：δ7.60(d,J＝7.4Hz,2H),7.51(m,1H),7.42(m,2H),1.53(s,9H).13C NMR(101MHz,CDCl3)：δ132.7,131.5,128.7,117.8,93.8,80.4,60.9,22.9.HRMS(ESI)calcd for C12H14O2S+:223.0787(M+H+),found:223.0780.
example 4:
to the reaction tube were added 0.2mmol of 4-fluorophenylacetylene bromide, 0.4mmol of sodium metabisulfite, 0.3mmol of potassium cyclopentylfluoroborate, 0.4mmol of ammonium fluoride and 2.0 mmol% of Mes-Acr in this order+ClO4 -The reaction tube is plugged with a rubber plug and placed in high-purity nitrogen for ventilation, 2.0mL of acetonitrile is added after the system is in an anaerobic condition, and the mixture is stirred and reacts under the irradiation of a 35W fluorescent lamp. After 48 hours of reaction, the reaction solution is directly concentrated under reduced pressure, column chromatography separation is carried out, and a mixed solution of petroleum ether and ethyl acetate is used as a mobile phase, so that the compound example 4 can be obtained. The yield was 54%.
Structural characterization of compound example 4:
1H NMR(400MHz,CDCl3)：δ7.61(d,J＝6.0Hz,2H),7.14(m,2H),3.78–3.60(m,1H),2.40–2.05(m,2H),1.99–1.69(m,2H).13C NMR(101MHz,CDCl3)：δ165.6,135.1(d,J＝9.0Hz),116.4(d,J＝22.4Hz),91.5,82.6,66.1,27.3,26.0.HRMS(ESI)calcd for C13H13FO2S+:253.0693(M+H+),found:253.0695.
example 5:
to the reaction tube were added 0.2mmol of 4-trifluoromethylphenylacetylene bromide, 0.4mmol of sodium metabisulfite, 0.3mmol of cyclopentylpotassium fluoroborate, 0.4mmol of ammonium fluoride and 2.0 mmol% of Mes-Acr in this order+ClO4 -The reaction tube is plugged with a rubber plug and placed in high-purity nitrogen for ventilation, 2.0mL of acetonitrile is added after the system is in an anaerobic condition, and the mixture is stirred and reacts under the irradiation of a 35W fluorescent lamp. After the TCL monitoring reaction is completed, directly carrying out reduced pressure concentration on the reaction liquid, carrying out column chromatography separation, and using a mixed liquid of petroleum ether and ethyl acetate as a mobile phase to obtain a compound example 5. The yield was 58%.
Structural characterization of compound example 5:
1H NMR(400MHz,CDCl3)：δ7.70(d,J＝2.1Hz,2H),7.26(m,2H),3.77–3.59(m,1H),2.21(m,4H),1.95–1.63(m,4H).13C NMR(101MHz,CDCl3)：δ133.0,125.6,121.6,90.1,84.5,66.1,27.2,25.9.HRMS(ESI)calcd for C14H13F3O2SNa+:325.0481(M+Na+),found:325.0497.
example 6:
to the reaction tube were added 0.2mmol of 3-methylphenylacetylenebromide, 0.4mmol of sodium metabisulfite, 0.3mmol of cyclopentylpotassium fluoroborate, 0.4mmol of ammonium fluoride and 2.0 mmol% of Mes-Acr in this order+ClO4 -The reaction tube is plugged with a rubber plug and placed in high-purity nitrogen for ventilation, 2.0mL of acetonitrile is added after the system is in an anaerobic condition, and the mixture is stirred and reacts under the irradiation of a 35W fluorescent lamp. After 48 hours of reaction, the reaction solution was directly concentrated under reduced pressure, column chromatography was performed, and a mixed solution of petroleum ether and ethyl acetate was used as a mobile phase, whereby compound example 6 was obtained. The yield was 62%.
Structural characterization of compound example 6:
1H NMR(400MHz,CDCl3)：δ7.39(m,2H),7.30(d,J＝7.5Hz,2H),3.67(m,1H),2.37(s,3H),2.20(m,4H),1.90–1.68(m,4H).13C NMR(101MHz,CDCl3)：δ138.6,133.1,132.4,129.8,128.6,117.6,92.9,82.2,66.2,27.3,26.0 21.1.HRMS(ESI)calcd for C14H16O2S+:249.0944(M+H+),found:249.0945.
it will be appreciated by persons skilled in the art that the above examples are illustrative only and not intended to be limiting of the invention, and that modifications to the above-described embodiments will fall within the scope of the appended claims provided they fall within the true spirit of the invention.
Claims (8)
1. A method for synthesizing aryl acetylene alkyl sulfone compounds based on alkyl fluoborate is characterized in that under the condition of visible light, a photosensitizer acts on the alkyl fluoborate to generate alkyl free radicals, the alkyl free radicals and sulfur dioxide provided by a sulfur dioxide solid substitute are combined to generate alkyl sulfonyl free radicals, and the alkyl sulfonyl free radicals and aryl acetylene bromine react to obtain the aryl acetylene alkyl sulfone compounds, and comprises the following steps:
(1) at room temperature, adding aryl acetylene bromide, a sulfur dioxide solid substitute, alkyl fluoborate, ammonium fluoride and a photosensitizer into a reaction tube according to a certain molar ratio, placing the reaction tube in a protective atmosphere to fully replace gas, adding a solvent, and reacting under the condition of visible light;
(2) after the reaction is completed, concentrating the reaction liquid, and carrying out column chromatography separation on the concentrated reaction liquid to obtain an aryl acetylene alkyl sulfone compound;
wherein the sulfur dioxide solid substitute is sodium metabisulfite, potassium metabisulfite or DABCO.(SO2)2At least one of;
the aryl of the aryl acetylene bromide is an aryl with or without an electron-withdrawing group or an electron-donating group, the electron-withdrawing group is at least one of fluorine, chlorine, bromine or trifluoromethyl, and the electron-donating group is at least one of alkyl, methoxy or phenyl;
the photosensitizer is Mes-Acr+ClO4 -。
2. The method for synthesizing the aryl acetylene alkyl sulfone compound based on the alkyl fluoroborate as claimed in claim 1, wherein the alkyl fluoroborate is potassium alkyl fluoroborate.
3. The method for synthesizing the aryl acetylene alkyl sulfone compound based on the alkyl fluoroborate as claimed in claim 1 or 2, wherein the alkyl group of the alkyl fluoroborate is at least one of ethyl, propyl, tert-butyl, cyclopentyl or cyclohexyl.
4. The method for synthesizing the aryl acetylene alkyl sulfone compound based on the alkyl fluoborate as claimed in claim 1, wherein the molar ratio of the aryl acetylene bromide, the sulfur dioxide solid substitute, the alkyl fluoborate, the ammonium fluoride and the photosensitizer in the step (1) is 1: (1.5-2.5): (1.0-2.0): (1.0-3.0): (0.05-0.25).
5. The method for synthesizing the aryl acetylene alkyl sulfone compound based on the alkyl fluoroborate as claimed in claim 1, wherein the protective atmosphere in the step (1) is at least one of nitrogen or argon.
6. The method for synthesizing the aryl acetylene alkyl sulfone compound based on the alkyl fluoborate as claimed in claim 1, wherein the solvent in the step (1) is an organic solvent, and the amount of the solvent is 10mL/mmol based on the amount of the aryl acetylene bromide.
7. The method for synthesizing the aryl acetylene alkyl sulfone compound based on the alkyl fluoroborate as claimed in claim 6, wherein the organic solvent is at least one of acetonitrile or 1, 2-dichloroethane.
8. The method for synthesizing the aryl acetylene alkyl sulfone compound based on the alkyl fluoroborate as claimed in claim 1, wherein the visible light in the step (1) is a 35W fluorescent lamp.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106045955A (en) * | 2016-07-11 | 2016-10-26 | 复旦大学 | Method for preparing 3-sulfonyl coumarin compound |
| CN109336860A (en) * | 2018-10-12 | 2019-02-15 | 嘉兴学院 | A kind of 3- mesyl -2- replaces the preparation method of benzothienyl compounds |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106045955A (en) * | 2016-07-11 | 2016-10-26 | 复旦大学 | Method for preparing 3-sulfonyl coumarin compound |
| CN109336860A (en) * | 2018-10-12 | 2019-02-15 | 嘉兴学院 | A kind of 3- mesyl -2- replaces the preparation method of benzothienyl compounds |
Non-Patent Citations (3)
| Title |
|---|
| Visible-Light-Induced Chemoselective Deboronative Alkynylation under Biomolecule-Compatible Conditions;Hanchu Huang 等;《Journal of the American Chemical Society》;20140203;第136卷;第2280-2283页 * |
| 利用多样性导向合成策略构建几类小分子化合物骨架;叶盛青;《复旦大学博士学位论文》;20150331;第1-295页 * |
| 氧杂蒽类有机染料在可见光诱导有机合成中的应用;徐雯秀 等;《有机化学》;20180716;第38卷;第2807-2832页 * |
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