Method for synthesizing 2, 3, 6-triphenylpyridine compound

Abstract

The invention belongs to the technical field of organic synthesis, and discloses a method for synthesizing a 2, 3, 6-triphenylpyridine compound, which comprises the following steps: preparing a Pd / ETS-10 catalyst, taking a phenylacetylene compound and a benzylamine compound as substrates, and realizing oxidative coupling-cycloaddition reaction of terminal alkyne and benzylamine in an oxygen atmosphere under the catalytic action of Pd / ETS-10, thereby obtaining the 2, 3, 6-triphenylpyridine compound. The triphenylpyridine compound is synthesized by a one-pot method, the synthesis method is high in atom economy, the catalyst can be recycled for multiple times, and the triphenylpyridine compound has good stability and high economic value.

Description

Technical Field

[0001] The invention belongs to the technical field of organic synthesis, and develops a simple catalytic system for synthesizing triphenylpyridine compounds, specifically a reaction for synthesizing triphenylpyridine compounds in one pot under the action of Pd / ETS-10, using phenylacetylene compounds and benzylamine compounds as substrates. Background Art

[0002] Pyridine derivatives are a class of heterocyclic compounds with important biological activities and application potential. They are important structural units of various alkaloids, drugs, agrochemicals, natural products, optoelectronic materials and electrochemical materials. 2,3,6-Triphenylpyridine is one of the most common pyridine derivatives. It is traditionally synthesized by the cycloaddition reaction of alkynes and benzylamines. However, the low availability, high price and poor reactivity of diacetylenes have greatly limited the wide application of this process. In order to overcome these limitations, scientific researchers have invested a lot of research to develop alternative synthetic methods to prepare 2,3,6-triphenylpyridine with cheap and readily available raw materials.

[0003] Titanosilicate ETS-10 is a widely used solid base catalyst. The octahedral coordinated titanium species produces two negative charges and has electron donor properties. The electron donating properties of this Lewis base will adsorb and activate electron-deficient substrates. In addition, the introduced ionic metal can coordinate with the framework oxygen atoms in the zeolite, resulting in changes in the electronic and geometric configuration of the metal.

[0004] In the present invention, under the reaction conditions without the need for additional additives, in an oxygen atmosphere, with cheap phenylacetylene and benzylamine as raw materials, an oxidative coupling-cycloaddition reaction of phenylacetylene and benzylamine is achieved on a Pd catalyst supported on an ETS-10 zeolite to prepare 2,3,6-triphenylpyridine. Summary of the invention

[0005] The present invention provides a method for generating 2,3,6-triphenylpyridine by one-step oxidative coupling cyclization using phenylacetylene and benzylamine as raw materials in a simple heterogeneous catalyst system. The Pd / ETS-10 catalyst prepared by using ETS-10 zeolite as a carrier and introducing metal Pd into the zeolite carrier realizes the oxidative coupling-cycloaddition reaction of terminal alkynes and benzylamine in an oxygen atmosphere. The present invention has the following characteristics: high economic value, the catalyst can be recycled for many times; one-pot synthesis is adopted, and the atom economy is high.

[0006] In order to achieve the above object, the technical solution of the present invention is:

[0007] Phenylacetylene compounds and benzylamine compounds are used as reaction substrates, and a certain amount of Pd / molecular sieve catalyst is added to the system. The target product is generated by reaction within a certain period of time under an oxygen atmosphere and a specific temperature. The reaction solution is then centrifuged and rotary evaporated, and 2,3,6-triphenylpyridine compounds are separated by column chromatography.

[0008] Reaction equation:

[0009]

[0010] R 1 , R 2 Each of them is independently hydrogen, alkyl and halogen.

[0011] Further, R 1 From hydrogen, 4-methyl, 3-methyl. 2 From hydrogen, 4-methyl, 4-fluoro, 4-chloro.

[0012] The reaction temperature of the present invention is 80 to 160°C, more preferably 120 to 140°C.

[0013] The reaction time of the present invention is 6 to 12 hours.

[0014] The reaction solvent of the present invention can be either N,N-dimethylformamide or dimethyl sulfoxide, with dimethyl sulfoxide being preferred.

[0015] The molar ratio of the phenylacetylene compound to the benzylamine compound of the present invention is 1:5-16, preferably 1:8-11.

[0016] The dosage relationship of the Pd / molecular sieve catalyst and the phenylacetylene compound of the present invention is: 10-40 mg: 0.1-0.3 mmol.

[0017] The molecular sieve of the present invention is one of mesoporous ETS-10, mesoporous ZSM-5 and mesoporous Silicalite-1; mesoporous ETS-10 is more preferred.

[0018] The catalyst Pd / ETS-10 is synthesized by an equal volume impregnation method. The source of the carrier ETS-10 zeolite is not limited. The loaded metal salt can be palladium nitrate, palladium acetate, or palladium chloride. The loading amount of metal Pd is 0.5-1.5wt.%, and more preferably 1wt.%. The Lewis basic site of ETS-10 and the incorporated metal together constitute a catalytic active center, which may bring unique catalytic activity and selectivity to the oxidative coupling-cycloaddition reaction of phenylacetylene and benzylamine.

[0019] Further preferred: a catalyst is prepared from mesoporous ETS-10 and palladium nitrate. The specific surface area of ​​the mesoporous ETS-10 is 250-270 m 2 / g, and the mesopore volume is 0.10~0.20cm 3 / g, with an external surface area of ​​64 to 110 m 2 / g, micropore volume is 0.11~0.16cm 3 / g.

[0020] As a preferred method, the preparation method of mesoporous ETS-10 zeolite is as follows: water glass and NaOH solution are added to a container to obtain solution A, KF solution is added to another container, and then TiCl is slowly added dropwise. 3 Solution B is obtained, and solution B is slowly added dropwise to solution A. After the system is stirred for 30 to 60 minutes, a 7# template agent is added dropwise thereto to obtain a gel. The gel is loaded into a polytetrafluoroethylene-lined reactor and crystallized at 180 to 220°C for 48 to 80 hours in a static state. After crystallization, the solution is washed with water, filtered and dried, and calcined at 450 to 500°C to obtain zeolite mesoporous ETS-10. The molar ratio of the raw material components in the gel is: 1.0TiO 2 :6.5~8.5SiO 2 :4.5~5.0Na 2 O:2.5~3.5KF:190~230H 2 O. 7# template agent is a polymer quaternary ammonium salt, purchased from Hangzhou Yinhu Chemical Co., Ltd. The volume ratio of 7# template agent to water glass is 1:2-7.

[0021] Advantages of the present invention:

[0022] (1) The present invention realizes the oxidative coupling-cycloaddition reaction of phenylacetylene and benzylamine on a Pd catalyst supported on ETS-10 zeolite under reaction conditions without the need for additional additives in an oxygen atmosphere, using inexpensive phenylacetylene compounds and benzylamine compounds as raw materials, thereby preparing 2,3,6-triphenylpyridine. The reaction conditions are simple, the atom economy is high, and only inexpensive substrates are required to efficiently synthesize the target product.

[0023] (2) Zeolite catalysts are non-toxic and harmless, easy to separate and recycle, and can be reused many times. They have good stability and high economic value. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 is the 2,3,6-triphenylpyridine in Example 1 1 H-NMR spectrum.

[0025] Figure 2 This is the HRMS (EI) spectrum of 2-(4-methylphenyl)-3,6-diphenylpyridine in Example 5.

[0026] Figure 3This is the HRMS (EI) spectrum of 2-(4-fluorophenyl)-3,6-diphenylpyridine in Example 6.

[0027] Figure 4 This is the HRMS (EI) spectrum of 2-(4-chlorophenyl)-3,6-diphenylpyridine in Example 7.

[0028] Figure 5 It is the HRMS (EI) spectrum of 2-phenyl-3,6-di(4-methylphenyl)-pyridine in Example 8.

[0029] Figure 6 This is the HRMS (EI) spectrum of 2-(4-methylphenyl)-3,6-di(4-methylphenyl)-pyridine in Example 9.

[0030] Figure 7 It is the HRMS (EI) spectrum of 2-(4-fluorophenyl)-3,6-di(4-methylphenyl)-pyridine in Example 10. DETAILED DESCRIPTION

[0031] The specific embodiments of the present invention are described below, but are not limited to the following examples, and the reaction conditions should be changed according to the actual situation. Unless otherwise specified, the reagents and instruments used in the following examples are commercially available products.

[0032] Specific preparation method of zeolite used in the scheme:

[0033] Weigh 3.2g NaOH and add 16mL distilled water to prepare NaOH solution, then add 20.7mL water glass to obtain solution A; weigh 4.51g KF·2H 2 O was added with 27.6 mL of distilled water to prepare KF solution. After obtaining a clear solution, 14.08 g of TiCl 3 Solution B was obtained; after stirring for 30 minutes, solution B was added dropwise to solution A, and after stirring for 60 minutes, 10 mL of 20 wt.% 7# template agent was added dropwise thereto, and stirring was continued for 90 minutes. The obtained gel was placed in a polytetrafluoroethylene-lined reactor and crystallized at 190°C for 72 hours in a static state. After neutral washing with water, filtration and drying, calcination at 450°C for 4 hours, the mesoporous zeolite ETS-10 was obtained. The molar ratio of the reaction gel system was 1.0TiO 2 :7.7SiO 2 :4.9Na 2 O:3.1KF:222H 2 O.

[0034] Pd / ETS-10: Weigh 0.0250g of palladium nitrate in an appropriate amount of distilled water to prepare a palladium nitrate metal salt solution of equal volume, add it dropwise to 1.0000g of mesoporous ETS-10 zeolite by impregnation method, let it stand at room temperature overnight, and then put it in 100℃ drying for 10h to obtain a mesoporous 1% Pd / ETS-10 zeolite catalyst. It is used in the following examples.

[0035] Embodiment 1:

[0036]

[0037] 30 mg 1% Pd / ETS-10 zeolite, 0.3 mmol phenylacetylene, 3 mmol benzylamine, and 1 mL dimethyl sulfoxide were added to a 10 mL Schlenk reaction tube, and the mixture was reacted in a 140° C. heater in an oxygen atmosphere for 7 h, then cooled and filtered, and the conversion rate and selectivity were analyzed using liquid chromatography (LC). The final yield of triphenylpyridine was calculated to be 99%, and the product was then separated and purified by thin layer chromatography, specifically using petroleum ether and ethyl acetate as eluents, and eluted and separated by silica gel column chromatography to obtain the product. The characterization data of the product are as follows:

[0038] 1 H-NMR (400MHz, CDCl 3 )δ8.16–8.14(m,2H),7.78–7.77(m,2H),7.51–7.42(m,5H),7.30–7.21(m,9H)

[0039] When the palladium loading mass in the Pd / ETS-10 zeolite of Example 1 was increased to 2%, the conversion rate and selectivity were measured by LC, and the target product triphenylpyridine was not obtained.

[0040] When the palladium loading mass in the Pd / ETS-10 zeolite of Example 1 was increased to 3%, the conversion rate and selectivity were measured by LC, and the target product triphenylpyridine was not obtained.

[0041] Embodiment 2:

[0042] A 10 mL Schlenk reaction tube was used as a container for the reaction system. 30 mg 1% Pd / ETS-10 zeolite, 0.3 mmol phenylacetylene, 3 mmol benzylamine, and 1 mL N,N-dimethylformamide were added to the reaction tube. The reaction was carried out in a 140° C. heater under an oxygen atmosphere for 7 h. After cooling to room temperature, the reaction solution was filtered. The conversion rate and selectivity of the reaction were analyzed using liquid chromatography (LC). The final calculated yield of triphenylpyridine was 48%. The remaining organic mixture was separated by column chromatography or thin layer chromatography, specifically, a mixture of petroleum ether (PE) and ethyl acetate (EA) was used as an eluent (developing agent), and silica gel column chromatography was used for elution and separation to obtain the product.

[0043] Embodiment 3:

[0044] If the reaction temperature in Example 1 is changed to 120° C. and other conditions remain unchanged, the conversion rate and selectivity are measured by LC, and the yield of triphenylpyridine is 93%.

[0045] If the reaction temperature in Example 1 is changed to 110° C. and other conditions remain unchanged, the conversion rate and selectivity are measured by LC, and the yield of triphenylpyridine is 52%.

[0046] If the reaction temperature in Example 1 is changed to 100° C. and other conditions remain unchanged, the conversion rate and selectivity are measured by LC, and the yield of triphenylpyridine is 44%.

[0047] Embodiment 4:

[0048] In a 10mL Schlenk reaction tube, 30mg1% Pd / ETS-10 zeolite, 0.3mmol phenylacetylene, 3mmol benzylamine, and 1mL DMSO (dimethyl sulfoxide) were added, and the mixture was reacted in a 140°C heater in an oxygen atmosphere for 3h, then cooled and filtered, and the conversion rate and selectivity were analyzed by liquid chromatography (LC). The final yield of triphenylpyridine was calculated to be 88%, and the product was then separated and purified by thin layer chromatography. Specifically, petroleum ether and ethyl acetate were used as eluents, and silica gel column chromatography was used for elution and separation to obtain the product.

[0049] If the time in Example 4 is changed to 5 h, and other conditions remain unchanged, the conversion rate and selectivity are determined by LC, and the yield of triphenylpyridine is 97%.

[0050] Embodiment 5:

[0051]

[0052] In a 10mL Schlenk reaction tube, 30mg 1% Pd / ETS-10 zeolite, 0.3mmol phenylacetylene, 3mmol 4-methylbenzylamine, and 1mL DMSO (dimethyl sulfoxide) were added, and the mixture was reacted in a 140°C heater in an oxygen atmosphere for 7h, then cooled and filtered, and the conversion rate and selectivity were analyzed by liquid chromatography (LC). The final yield of 2-(4-methylphenyl)-3,6-diphenylpyridine was calculated to be 97%, and then thin layer chromatography was used to separate and purify the product, specifically using petroleum ether and ethyl acetate as eluents, and silica gel column chromatography was used to elute and separate the product. The characterization data of the product are as follows:

[0053] m / z:321.15(100.0%),322.16(26.2%),323.16(3.3%)

[0054] Embodiment 6:

[0055]

[0056] In a 10mL Schlenk reaction tube, 30mg 1% Pd / METS-10 zeolite, 0.3mmol phenylacetylene, 3mmol 4-fluorobenzylamine, and 1mL DMSO (dimethyl sulfoxide) were added. The mixture was reacted in an oxygen atmosphere in a 140°C heater for 7h, then cooled and filtered. The conversion rate and selectivity were analyzed using liquid chromatography (LC). The final yield of 2-(4-fluorophenyl)-3,6-diphenylpyridine was 74%. The product was then separated and purified by thin layer chromatography. Specifically, petroleum ether and ethyl acetate were used as eluents, and silica gel column chromatography was used for elution and separation to obtain the product. The characterization data of the product are as follows:

[0057] m / z:325.13(100.0%),326.13(25.1%),327.13(3.1%)

[0058] Embodiment 7:

[0059]

[0060] In a 10mL Schlenk reaction tube, 30mg 1% Pd / METS-10 zeolite, 0.3mmol phenylacetylene, 3mmol 4-chlorobenzylamine, and 1mL DMSO (dimethyl sulfoxide) were added. The mixture was reacted in a 140°C heater in an oxygen atmosphere for 7h, then cooled and filtered. The conversion rate and selectivity were analyzed using liquid chromatography (LC). The final yield of 2-(4-chlorophenyl)-3,6-diphenylpyridine was 62%. The product was then separated and purified by thin layer chromatography. Specifically, petroleum ether and ethyl acetate were used as eluents, and silica gel column chromatography was used for elution and separation to obtain the product. The characterization data of the product are as follows:

[0061] m / z: 341.10 (100.0%), 343.09 (32.0%), 342.10 (25.1%), 344.10 (8.0%), 343.10 (3.1%), 345.10 (1.0%)

[0062] Embodiment 8:

[0063]

[0064] In a 10mL Schlenk reaction tube, 30mg 1% Pd / ETS-10 zeolite, 0.3mmol 4-methylphenylacetylene, 3mmol benzylamine, and 1mL DMSO (dimethyl sulfoxide) were added, and the mixture was reacted in a 140°C heater in an oxygen atmosphere for 7h, then cooled and filtered, and the conversion rate and selectivity were analyzed by liquid chromatography (LC). The final yield of 2-phenyl-3,6-di(4-methylphenyl)-pyridine was calculated to be 90%, and then thin layer chromatography was used to separate and purify the product, specifically using petroleum ether and ethyl acetate as eluents, and silica gel column chromatography was used to elute and separate the product. The characterization data of the product are as follows:

[0065] m / z:335.17(100.0%),336.17(27.3%),337.17(3.6%)

[0066] Embodiment 9:

[0067]

[0068] In a 10mL Schlenk reaction tube, 30mg 1% Pd / ETS-10 zeolite, 0.3mmol 4-methylphenylacetylene, 3mmol 4-methylbenzylamine, and 1mL DMSO (dimethyl sulfoxide) were added, and the mixture was reacted in a 140°C heater in an oxygen atmosphere for 7h, then cooled and filtered, and the conversion rate and selectivity were analyzed by liquid chromatography (LC). The final yield of 2-(4-methylphenyl)-3,6-di(4-methylphenyl)-pyridine was calculated to be 95%, and then thin layer chromatography was used to separate and purify the product, specifically using petroleum ether and ethyl acetate as eluents, and silica gel column chromatography was used to elute and separate the product. The characterization data of the product are as follows:

[0069] m / z:349.18(100.0%),350.19(28.4%),351.19(3.9%)

[0070] Embodiment 10:

[0071]

[0072] In a 10mL Schlenk reaction tube, 30mg 1% Pd / ETS-10 zeolite, 0.3mmol 4-methylphenylacetylene, 3mmol 4-fluorobenzylamine, and 1mL DMSO (dimethyl sulfoxide) were added, and the mixture was reacted in a 140°C heater in an oxygen atmosphere for 7h, then cooled and filtered, and the conversion rate and selectivity were analyzed by liquid chromatography (LC). The final yield of 2-(4-fluorophenyl)-3,6-di(4-methylphenyl)-pyridine was 76%, and then thin layer chromatography was used to separate and purify the product, specifically using petroleum ether and ethyl acetate as eluents, and silica gel column chromatography was used to elute and separate the product. The characterization data of the product are as follows:

[0073] m / z:353.16(100.0%),354.16(27.6%),355.16(3.6%)

[0074] Embodiment 12:

[0075] Compared with Example 1, Example 12 differs in that ETS-10 is replaced by Silicalite-1.

[0076] The preparation method of Pd / Silicalite-1 catalyst is the same as that of Pd / ETS-10. The source of Silicalite-1 is prepared by referring to the method in "Journal of Industrial and Engineering Chemistry, 95, 2021, 376-387".

[0077] 30 mg of 1% Pd / Silicalite-1 zeolite, 0.3 mmol of phenylacetylene, 3 mmol of benzylamine, and 1 mL of DMSO (dimethyl sulfoxide) were added to a reaction tube, and the reaction was carried out in a 140° C. heater in an oxygen atmosphere for 7 h. The reaction was then cooled and filtered. The conversion rate and selectivity were analyzed by liquid chromatography (LC). The final yield of triphenylpyridine was calculated to be 43%. The product was then separated and purified by thin layer chromatography. Specifically, petroleum ether and ethyl acetate were used as eluents, and silica gel column chromatography was used for elution and separation to obtain the product.

[0078] Embodiment 13:

[0079] Compared with Example 1, Example 13 is different in that ETS-10 is replaced by ZSM-5. The preparation method of Pd / ZSM-5 zeolite is the same as that of Pd / ETS-10. The source of ZSM-5 is prepared according to the previously published "Journal of Catal. 330, 2015, 423-433".

[0080] 30 mg of 1% Pd / ZSM-5 zeolite, 0.3 mmol of phenylacetylene, 3 mmol of benzylamine, and 1 mL of DMSO (dimethyl sulfoxide) were added to a reaction tube, and the reaction was carried out in a 140°C heater in an oxygen atmosphere for 7 hours. The reaction was then cooled and filtered. The conversion rate and selectivity were analyzed by liquid chromatography (LC). The final yield of triphenylpyridine was calculated to be 65%. The product was then separated and purified by thin layer chromatography. Specifically, petroleum ether and ethyl acetate were used as eluents, and silica gel column chromatography was used for elution and separation to obtain the product.

[0081] Comparative Example 1:

[0082] 30 mg of palladium nitrate, 0.3 mmol of phenylacetylene, 3 mmol of benzylamine, and 1 mL of DMSO (dimethyl sulfoxide) were added to a reaction tube, and the mixture was reacted in a 140°C heater in an oxygen atmosphere for 7 h. The mixture was then cooled and filtered. The conversion rate and selectivity were analyzed using liquid chromatography (LC), and it was found that no target product was generated.

[0083] Comparative Example 2:

[0084] Comparative Example 2 is different from Example 1, except that Pd / ETS-10 is replaced with ETS-10. 30 mg ETS-10, 0.3 mmol phenylacetylene, 3 mmol benzylamine, and 1 mL DMSO (dimethyl sulfoxide) are added to the reaction tube, and the mixture is reacted in a 140° C. heater in an oxygen atmosphere for 7 h, then cooled and filtered, and the conversion rate and selectivity are analyzed by liquid chromatography (LC), and it is found that no target product is generated. Comparative Example 3:

[0085] 1% Pd / C, 0.3 mmol of phenylacetylene, 3 mmol of benzylamine, and 1 mL of DMSO (dimethyl sulfoxide) were added to the reaction tube. The mixture was reacted in an oxygen atmosphere in a 140°C heater for 7 hours. The mixture was then cooled and filtered. The conversion rate and selectivity were analyzed by liquid chromatography (LC), and 20% of the target product was found to be generated.

[0086] Comparative Example 4:

[0087] Comparative Example 4 is compared with Example 1, except that the preparation method of Pd / ETS-10 is different: 0.0250g of palladium nitrate is weighed in an appropriate amount of distilled water, and a palladium nitrate metal salt solution is prepared, and an equal volume impregnation method is used to add it dropwise to 1.0000g of ETS-10 zeolite, and the solution is allowed to stand at room temperature overnight, and then dried at 100°C for 10h, and then calcined at 450°C to obtain Pd / ETS-10.

[0088] 30 mg of calcined Pd / ETS-10, 0.3 mmol of phenylacetylene, 3 mmol of benzylamine, and 1 mL of DMSO (dimethyl sulfoxide) were added to the reaction tube. The mixture was reacted in an oxygen atmosphere in a 140°C heater for 7 h. The mixture was then cooled and filtered. The conversion rate and selectivity were analyzed using liquid chromatography (LC), and it was found that only 15% of the target product was produced.

[0089] The above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit the same. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that the technical solutions described in the aforementioned embodiments may still be modified, or some of the technical features may be replaced by equivalents. However, these modifications or replacements do not deviate the essence of the corresponding technical solutions from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A method for synthesizing 2,3,6-triphenylpyridine compounds, characterized in that: The phenylacetylene compound shown in Formula 1 and the benzylamine compound shown in Formula 2 are added to a solvent, a Pd / molecular sieve catalyst is added thereto, and the mixture is reacted under an oxygen atmosphere and heating conditions, and the reaction liquid is separated and purified after the reaction to obtain a 2,3,6-triphenylpyridine compound shown in Formula 3; wherein the loading amount of metal Pd on the molecular sieve is 1 to 1.5 wt.%; R1 and R2 are independently hydrogen, alkyl and halogen respectively; the molecular sieve is one of mesoporous ETS-10, ZSM-5 and Silicalite-1.

2. The method for synthesizing 2,3,6-triphenylpyridine compounds according to claim 1, characterized in that: The reaction temperature is 80-160°C; the reaction time is 6-24h.

3. The method for synthesizing 2,3,6-triphenylpyridine compounds according to claim 1, characterized in that: The solvent is one or a mixture of N,N-dimethylformamide and dimethyl sulfoxide.

4. The method for synthesizing 2,3,6-triphenylpyridine compounds according to claim 1, characterized in that: The molar ratio of the phenylacetylene compound to the benzylamine compound is 1:5-16.

5. The method for synthesizing 2,3,6-triphenylpyridine compounds according to claim 1, characterized in that: The preparation method of Pd / molecular sieve catalyst is as follows: weigh an appropriate amount of palladium nitrate in distilled water, prepare a palladium nitrate metal salt solution of equal volume, add it dropwise into the molecular sieve zeolite by impregnation method, let it stand at room temperature, and then put it into 100°C for drying to obtain Pd / molecular sieve catalyst.

6. The method for synthesizing 2,3,6-triphenylpyridine compounds according to claim 1, characterized in that: The molecular sieve is mesoporous ETS-10; the structural specific surface area of ​​mesoporous ETS-10 is 250-270m 2 / g, and the mesopore volume is 0.10~0.20cm 3 / g, with an external surface area of ​​64 to 110 m 2 / g, micropore volume is 0.11~0.16cm 3 / g.

Images