Preparation of mesoporous cuprous oxide material and application of mesoporous cuprous oxide material in catalysis of chiral boron addition reaction

Abstract

The invention relates to the technical field of synthesis of chiral boron compounds, in particular to preparation of a mesoporous cuprous oxide material and application of the mesoporous cuprous oxide material in catalytic chiral boron addition reaction. The preparation process of the catalyst mesoporous cuprous oxide comprises the following steps: (1) adding a triblock copolymer P123 (PEO-PPO-PEO) into deionized water, and stirring at room temperature to obtain a system I; (2) adding a copper ammonia solution into the system I obtained in the step (1), and stirring at room temperature to obtain a system II; (3) adding mesitylene (TMB) into the system II obtained in the step (2), and stirring at room temperature to obtain a system III; (4) adding ascorbic acid (AA) into the system III obtained in the step (3), and stirring at room temperature to obtain a system IV; and (5) cleaning the system IV obtained in the step (4) with ethanol and water which are mixed in equal volume for three times, and drying in a vacuum drying oven to obtain the catalyst. The raw materials of the catalyst are cheap and easy to obtain, the preparation is simple, and higher yield and enantioselectivity can be obtained only by using a lower catalyst dosage.

Description

Technical Field

[0001] The invention relates to the technical field of chiral boron compound synthesis, and in particular to the preparation of a mesoporous cuprous oxide material and application of the mesoporous cuprous oxide material in catalyzing chiral boron addition reactions. Background Art

[0002] Chiral organoboron compounds are commonly found in bioactive compounds and can be used as chiral intermediates in the synthesis of important organic molecules. Many bioactive drugs such as tal abostat, bortezomib, and delanzomib contain functional organoboron groups, which are key drugs for the treatment of various skin diseases or tumors. Chiral boron derivatives have been widely used in chemical bond transformation while maintaining the integrity of the stereocenter. The conjugate addition of boron reagents is one of the most effective and basic strategies for constructing CB bonds.

[0003] Porous nanocatalysts have a large specific surface area and high porosity, which allows reactant molecules to more easily access the active sites of the catalyst, thereby greatly improving the catalytic reaction rate and efficiency, while also having good controllability and stability. In contrast, conventional catalysts have a small specific surface area, a limited number of active sites, and a relatively low catalytic efficiency.

[0004] Copper has attracted much attention due to its affordable price and excellent catalytic performance. However, Cu(I) nanomaterials are rarely used to catalyze chiral α,β-unsaturated carbonyl compounds. Therefore, there is an urgent need to solve this problem.

[0005] The above contents are only used to assist in understanding the technical solution of the present invention, and do not constitute an admission that the above contents are the closest prior art. Summary of the invention

[0006] The technical problem to be solved by the present invention is to provide a preparation method of a mesoporous cuprous oxide material and an application thereof in catalyzing a chiral boron addition reaction. The prepared mesoporous cuprous oxide material not only realizes the transformation of α, β, γ, δ-unsaturated compounds into borate-substituted carbonyl compounds, and obtains a higher yield and enantioselectivity value, but also avoids the use of a strong base in the process, has mild conditions, low cost, and is environmentally friendly.

[0007] To achieve the above object, the technical solution of the present invention is implemented as follows: a preparation of a mesoporous cuprous oxide material and its application in catalyzing chiral boron addition reaction; the preparation steps of the mesoporous cuprous oxide are as follows:

[0008] (1) adding the triblock copolymer P123 (PEO-PPO-PEO) into deionized water and stirring at room temperature to obtain system 1;

[0009] (2) adding the copper ammonia solution to the system 1 obtained in step (1), and stirring at room temperature to obtain the system 2;

[0010] (3) adding mesitylene (TMB) to the system 2 obtained in step (2), and stirring at room temperature to obtain the system 3;

[0011] (4) adding ascorbic acid (AA) to the system 3 obtained in step (3), and stirring at room temperature to obtain the system 4;

[0012] (5) The system 4 obtained in step (4) is washed three times with equal volumes of ethanol and water, and then dried in a vacuum drying oven at 40° C. to 60° C. for 6 to 12 hours to obtain a catalyst mesoporous cuprous oxide.

[0013] Preferably, the mass of the triblock copolymer P123 (PEO-PPO-PEO) in step (1) is 0.6-0.7 g, the concentration of the cuprammonium solution in step (2) is 0.1-0.3 M, and the amount used is 2-5 mL; the concentration of mesitylene in step (3) is 7-10 M, and the amount used is 0.5 -0.8 mL; the concentration of ascorbic acid in step (4) is 0.5-0.7 M, and the amount used is 4-6 mL.

[0014] Preferably, the stirring time at room temperature in step (1) is 2h-4h; the stirring time at room temperature in step (2) is 20-40min; the stirring time at room temperature in step (3) is 20-40min; and the stirring time at room temperature in step (4) is 20-40min.

[0015] Preferably, the application process comprises the following synthesis steps:

[0016] S1, adding α, β, γ, δ-unsaturated compounds, biboric acid pinacol ester, mesoporous cuprous oxide catalyst, and amine chiral ligand into a solvent, and stirring to react at room temperature;

[0017] S2, extracting, filtering, drying and rotary evaporating the system obtained in step S1 to obtain a crude boride product;

[0018] S3, stirring the crude boride product obtained in step S2 with the organic mixed solution, and then extracting, filtering, drying, rotary evaporating, and column chromatography to obtain a chiral boron compound;

[0019] The structural formula of the α, β, γ, δ-unsaturated compound is The chiral boron compound has the structural formula: Wherein R1 is phenyl or p-fluorophenyl; R2 is phenyl, p-bromophenyl or styryl; the amine chiral ligand is a chiral bipyridine ligand, and the structural formula is

[0020] Preferably, the solvent in step S1 is a mixed solvent of toluene and water, and the volume ratio of toluene to water is (1-9):(9-1).

[0021] Preferably, the molar ratio of the α, β, γ, δ-unsaturated compound, the biphenyl borate, the mesoporous cuprous oxide catalyst, and the amine chiral ligand in step S1 is 1:(1.2-2.0):(0.03-0.09):(0.03-0.09); the stirring reaction is stirred at room temperature for 3-12 hours.

[0022] Preferably, the extractant in step S2 is ethyl acetate; and the desiccant in step S2 is anhydrous sodium sulfate.

[0023] Preferably, the organic mixed solution in step S3 comprises NaBO3·4H2O, THF and deionized water, wherein the amount of NaBO3·4H2O is 367.0 mg, the amount of THF is 4.5 mL, and the amount of water is 3.0 mL.

[0024] Preferably, the reaction conditions in step S3 are stirring at room temperature for 3-6 hours.

[0025] Preferably, the extractant in step S3 is ethyl acetate, and the desiccant in step S3 is anhydrous sodium sulfate.

[0026] The beneficial effects of the present invention are embodied in:

[0027] (1) When the mesoporous cuprous oxide prepared by the invention is used as a catalyst, its unique nanoporous structure provides abundant binding sites for the catalytic reaction, thereby achieving high yield and high enantioselectivity of chiral boron compounds at a low catalyst amount. In addition, the application of the catalyst in the chiral boron addition reaction avoids the use of strong bases, has mild conditions, low cost, and is environmentally friendly.

[0028] (2) The mesoporous cuprous oxide prepared by the invention has significantly improved benefits when used as a catalyst, which is specifically manifested in the following aspects: 1) The synthesis method of the mesoporous cuprous oxide nanomaterial is simple, and the raw materials used are affordable, which reduces the production cost of the catalyst; 2) The catalyst cleaning process only uses deionized water and anhydrous ethanol, which are low-cost and easy to obtain, further simplifying the operation process and reducing costs; 3) The catalyst cleaning process only uses deionized water and anhydrous ethanol, which are low-cost and easy to obtain, further simplifying the operation process and reducing costs; 4) In the process of synthesizing chiral boron compounds, the method of the present invention achieves a high conversion rate, and the product is easy to separate, reducing the generation of by-products, simplifying subsequent processing steps, and further improving economic benefits.

[0029] (3) The present invention uses a large amount of green solvent, water, in the process of catalyst preparation and chiral boron compound synthesis, which reduces the use of harmful organic solvents and significantly reduces environmental pollution, which is in line with the concept of green chemistry and sustainable development.

[0030] (4) The production process of the present invention is safe and reliable, which is specifically manifested in the following aspects: 1) In the process of catalyst preparation and chiral boron compound synthesis, the present invention mainly uses water and anhydrous ethanol as solvents. These two solvents have low toxicity and low volatility, which greatly reduces the potential harm to operators in the production process; 2) In the process of catalyst preparation and chiral boron compound synthesis, the present invention mainly uses water and anhydrous ethanol as solvents. These two solvents have low toxicity and low volatility, which greatly reduces the potential harm to operators in the production process; 3) The production process mainly relies on magnetic stirring, which reduces the complexity of manual operation and labor costs, and at the same time facilitates the control of production progress, thereby improving the safety and controllability of the overall production. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 This is the XRD pattern of mesoporous cuprous oxide in Example 1;

[0032] Figure 2 This is the BET diagram of mesoporous cuprous oxide in Example 1;

[0033] Figure 3 is the H NMR spectrum of the target product in Example 2;

[0034] Figure 4 is the NMR carbon spectrum of the target product in Example 2;

[0035] Figure 5 The HPLC spectrum of the racemate of the target product in Example 2;

[0036] Figure 6 HPLC spectrum of the target product in Example 2;

[0037] Figure 7 is the H NMR spectrum of the target product in Example 3;

[0038] Figure 8 is the NMR carbon spectrum of the target product in Example 3;

[0039] Fig. 9 The HPLC spectrum of the racemate of the target product in Example 3;

[0040] Fig.10 HPLC spectrum of the target product in Example 3;

[0041] Fig.11 is the H NMR spectrum of the target product in Example 4;

[0042] Fig.12 is the NMR carbon spectrum of the target product in Example 4;

[0043] Fig.13The HPLC spectrum of the racemate of the target product in Example 4;

[0044] Fig.14 The HPLC spectrum of the target product in Example 4 is shown in FIG. DETAILED DESCRIPTION

[0045] The technical solutions in the embodiments of the present invention will be clearly and completely described below in conjunction with the drawings in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, rather than all of the embodiments. In the absence of conflict, the embodiments in this application and the features in the embodiments can be combined with each other. Based on the embodiments in the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0046] The working principle of the present invention is: the mesoporous cuprous oxide and B 2 (pi n) 2 First, a copper-boron complex is formed in a mixture of toluene and water, and then the copper-boron complex is conjugated with an α,β-unsaturated receptor to generate an organic copper species, and then water protonates the organic copper species to obtain the final product. The mesoporous cuprous oxide catalyst can be recycled and used in subsequent reactions. In the whole process, H 2 O acts as a proton source. Intermediate Bolm-Mesoporous Cu 2 The O complex promotes asymmetric conjugate boron addition, resulting in enantioselective generation of chiral compounds.

[0047] Example 1

[0048] Mesoporous cuprous oxide is prepared by the following method:

[0049] Add 0.612g of P123 to 30mL of deionized water and stir at room temperature for 3h to obtain system 1; add 2.25mL of 0.2M copper ammonia solution to system 1 and stir at room temperature for 30min to obtain system 2; add 0.7mL of 7M mesitylene to system 2 and stir at room temperature for 30min to obtain system 3; add 4.6mL of 0.6M ascorbic acid to system 3 and stir at room temperature for 20min to obtain system 4; the obtained system 4 is washed three times with equal volumes of mixed ethanol and water, and vacuum dried at 40℃-60℃ for 6-12h to obtain the corresponding mesoporous cuprous oxide.

[0050] Figure 1 The XRD pattern of mesoporous cuprous oxide shows that the characteristic diffraction peaks of the sample are similar to those of Cu 2 O (JCPDS No. 05-0667), proving that it is Cu 2 O.

[0051] Figure 2 This is a SEM image of mesoporous cuprous oxide. The porous structure can provide abundant binding sites, making it easier for metallic copper to bind to reactants and achieve rapid catalysis.

[0052] Example 2

[0053] The mesoporous cuprous oxide prepared in Example 1 is used as a catalyst in the reaction of synthesizing a chiral boron compound using (E)-3-(4-chlorophenyl)-1-(p-tolyl)prop-2-en-1-one as a substrate, comprising the following steps:

[0054] 1) 0.3 mM (E)-3-(4-chlorophenyl)-1-(p-tolyl)prop-2-en-1-one, 0.36 mM pinacol diboron ester reagent, 0.009 mM mesoporous cuprous oxide catalyst, and 0.0108 mM chiral Bol ligand were added to 2 mL of toluene: deionized water = 9:1 (v:v) solvent, and mixed and stirred at room temperature for 12 h; the chemical reaction formula is as follows:

[0055]

[0056] Chiral Ligand is a chiral ligand (Bolm ligand) with the structural formula

[0057] 2) After the reaction is completed, the obtained mixed system is centrifuged and filtered. The obtained liquid phase is extracted with ethyl acetate solution and anhydrous Na 2 SO 4 Drying and rotary evaporation give the crude boride product.

[0058] 3) Add 367.0 mg NaBO to the obtained 0.2 mmol crude boride product. 3 .4H 2 O, 4.5 mL THF and 3.0 mL deionized water were reacted at room temperature for 3 h, and the obtained mixed system was centrifuged and filtered. The obtained liquid phase was extracted with ethyl acetate solution and anhydrous Na 2 SO 4 Drying, filtering, rotary evaporation and column chromatography give a chiral hydroxy compound. The chemical reaction formula is as follows:

[0059]

[0060] The filtered precipitate is washed and dried to obtain the recovered mesoporous cuprous oxide catalytic material for next recycling.

[0061] Step 1) The mesoporous cuprous oxide catalytic material is applied to the chiral boron addition reaction of (E)-3-(4-chlorophenyl)-1-(p-tolyl)prop-2-en-1-one, and the yield and enantioselectivity of the target product (chiral boron-based compound) are 96% and 99%, respectively.

[0062] The target product has a hydrogen NMR spectrum, a carbon NMR spectrum and a HPLC spectrum. Figures 3 to 6 As shown, Figure 5 is the HPLC spectrum of the target product racemate, Figure 6 The HPLC spectrum of the synthesized target product is as follows:

[0063] 1 H NMR (400 MHz, CDCl 3 )δ7.84(d,J=8.3Hz,2H),7.42-7.31(m,4H),7.30-7.22(m,2H),5.30(dd,J=8.5,3.6Hz,1H),3.79(br s,1H),3.38-3.23(m,2H),2.42(s,3H).

[0064] 13 C NMR (100 MHz, CDCl 3 )δ199.7,144.8,141.5,133.9,133.3,129.5,128.7,128.3,127.2,69.5,47.1,21.8.

[0065] HPLC(Dialcel Chiralcel OD-H,n-hexane / i PrOH=85 / 15,flow rate 1.0

[0066] mL / min); tR=8.4min (S, minor), tR=9.4min (R, major).

[0067] Example 3

[0068] The mesoporous cuprous oxide prepared in Example 1 is used as a catalyst in the reaction of synthesizing a chiral boron compound using (E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one as a substrate, comprising the following steps:

[0069] 1) 0.3 mmol (E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one, 0.36 mM pinacol diboric acid ester reagent, 0.009 mM mesoporous cuprous oxide catalyst, and 0.0108 mM chiral Bolm ligand were added to 2 mL of toluene: deionized water = 9:1 (v:v) solvent, and the mixture was stirred at room temperature for 12 h. The chemical reaction formula is as follows:

[0070]

[0071] Chiral Ligand is a chiral ligand (Bolm ligand) with the structural formula

[0072] 2) After the reaction is completed, the obtained mixed system is centrifuged and filtered. The obtained liquid phase is extracted with ethyl acetate solution and anhydrous Na 2 SO 4 Drying and rotary evaporation give the crude boride product.

[0073] 3) Add 367.0 mg of NaBO to the obtained 0.3 mM crude boride product. 3 .4H 2 O, 4.5 mL THF and 3.0 mL deionized water were reacted at room temperature for 3 h, and the obtained mixed system was centrifuged and filtered. The obtained liquid phase was extracted with ethyl acetate solution and anhydrous Na 2 SO 4 Drying, filtering, rotary evaporation and column chromatography give a chiral hydroxy compound. The chemical reaction formula is as follows:

[0074]

[0075] The filtered precipitate is washed and dried to obtain the recovered mesoporous cuprous oxide catalytic material for next recycling.

[0076] Step 1) The mesoporous cuprous oxide catalytic material is applied to the chiral boron addition reaction of (E)-1-(4-fluorophenyl)-3-(thiophen-2-yl)prop-2-en-1-one, and the yield and enantioselectivity of the target product (chiral boron-based compound) are 97% and 98%, respectively.

[0077] The target product has a hydrogen NMR spectrum, a carbon NMR spectrum and a HPLC spectrum. Figures 7-10 As shown, Fig. 9 is the HPLC spectrum of the target product racemate, Fig.10 The HPLC spectrum of the synthesized target product is as follows:

[0078] 1 H NMR (400 MHz, CDCl 3)δ8.17-8.08(m,2H),7.44-7.37(m,1H),7.33-7.23(m,2H),7.19-7.14(m,1H),7.13-7.09(m,1H),5.73(dd,J=8.4,3.6Hz,1H),3.86(br s,1H),3.68-3.52(m,2H).

[0079] 13 C NMR (100 MHz, CDCl 3 )δ197.9,166.1(J C-F =284.3Hz),146.5,132.9(J C-F =2.9Hz),130.9(J C-F =9.4Hz),126.8,124.8,123.6,115.9(J C-F =11.8Hz),66.4,47.2.

[0080] HPLC(Dialcel Chiralcel OD-H,n-hexane / i PrOH=90 / 10,flow rate 1.0

[0081] mL / min); tR=15.6min (R, major), tR=16.9min (S, minor).

[0082] Example 4

[0083] The mesoporous iodine prepared in Example 1 is used as a copper catalyst in the reaction of synthesizing a chiral boron compound using (2E, 4E)-1-(4-methoxyphenyl)-5-phenylpenta-2,4-diene-1-one as a substrate, comprising the following steps:

[0084] 1) 0.3 mM (2E, 4E)-1-(4-methoxyphenyl)-5-phenylpenta-2,4-diene-1-one, 0.36 mM biboric acid pinacol ester reagent, 0.009 mM mesoporous cuprous oxide catalyst, and 0.0108 mM chiral Bolm ligand were added to 2 mL of toluene: deionized water = 9:1 (v:v) solvent, and mixed and stirred at room temperature for 12 h; the chemical reaction formula is as follows:

[0085]

[0086] Chiral Ligand is a chiral ligand (Bolm ligand) with the structural formula

[0087] 2) After the reaction is completed, the obtained mixed system is centrifuged and filtered. The obtained liquid phase is extracted with ethyl acetate solution and anhydrous Na 2 SO 4 Drying and rotary evaporation give the crude boride product.

[0088] 3) Add 367.0 mg of NaBO to the obtained 0.3 mM crude boride product. 3 .4H 2 O, 4.5 mL THF and 3.0 mL deionized water were reacted at room temperature for 3 h, and the obtained mixed system was centrifuged and filtered. The obtained liquid phase was extracted with ethyl acetate solution and anhydrous Na 2 SO 4 Drying, filtering, rotary evaporation and column chromatography give a chiral hydroxy compound. The chemical reaction formula is as follows:

[0089]

[0090] The filtered precipitate is washed and dried to obtain the recovered mesoporous cuprous oxide catalytic material for next recycling.

[0091] Step 1) The mesoporous cuprous oxide catalytic material is applied to the chiral boron addition reaction of (2E, 4E)-1-(4-methoxyphenyl)-5-phenylpenta-2,4-diene-1-one, and the yield and enantioselectivity of the target product (chiral boron-based compound) are 91% and 93%, respectively.

[0092] The target product has a hydrogen NMR spectrum, a carbon NMR spectrum and a HPLC spectrum. Figures 11 to 14 As shown, Fig.13 is the HPLC spectrum of the target product racemate, Fig.14 The HPLC spectrum of the synthesized target product is as follows:

[0093] 1 H NMR (400 MHz, CDCl 3 )δ7.90(d,J=8.9Hz,2H),7.34(d,J=7.0Hz,2H),7.26(t,J=7.4Hz,2H),7.22-7.14(m,1H),6.89(d,J =8.9Hz,2H),6.65(d,J=15.9Hz,1H),6.26(dd,J=15.9,6.0Hz,1H),3.82(s,3H),3.27-3.08(m,2H).

[0094] 13 C NMR (100 MHz, CDCl 3)δ198.7,164.0,136.6,130.5,130.4,129.7,128.6,127.7,127.3,126.5,113.9,68.8,55.6,44.7.

[0095] HPLC(Dialcel Chiralcel OD-H,n-hexane / i PrOH=90 / 10,flow rate 1.0

[0096] mL / min); tR=54.1min (R, major), tR=65.5min (S, minor).

[0097] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. A preparation method of a mesoporous cuprous oxide material, characterized in that: The preparation steps of the mesoporous cuprous oxide are as follows: (1) adding the triblock copolymer P123 into deionized water and stirring at room temperature to obtain system 1; (2) adding the copper ammonia solution to the system 1 obtained in step (1), and stirring at room temperature to obtain the system 2; (3) adding mesitylene to the system 2 obtained in step (2), and stirring at room temperature to obtain the system 3; (4) adding ascorbic acid to the system 3 obtained in step (3), and stirring at room temperature to obtain the system 4; (5) The system 4 obtained in step (4) is washed three times with equal volumes of ethanol and water, and then dried in a vacuum drying oven at 40° C. to 60° C. for 6 to 12 hours to obtain a catalyst mesoporous cuprous oxide.

2. The preparation of a mesoporous cuprous oxide material according to claim 1, characterized in that: The mass of the triblock copolymer P123 in step (1) is 0.6-0.7 g, the concentration of the copper ammonia solution in step (2) is 0.1-0.3 M, and the amount used is 2-5 mL; the concentration of mesitylene in step (3) is 7-10 M, and the amount used is 0.5-0.8 mL; the concentration of ascorbic acid in step (4) is 0.5-0.7 M, and the amount used is 4-6 mL.

3. The preparation of a mesoporous cuprous oxide material according to claim 1, characterized in that: The stirring time at room temperature in step (1) is 2h-4h; the stirring time at room temperature in step (2) is 20-40min; the stirring time at room temperature in step (3) is 20-40min; and the stirring time at room temperature in step (4) is 20-40min.

4. Use of the mesoporous cuprous oxide material prepared according to any one of claims 1 to 3 in catalyzing chiral boron addition reactions, characterized in that: The application process comprises the following synthesis steps: S1, adding α, β, γ, δ-unsaturated compounds, biboric acid pinacol ester, mesoporous cuprous oxide catalyst, and amine chiral ligand into a solvent, and stirring to react at room temperature; S2, extracting, filtering, drying and rotary evaporating the system obtained in step S1 to obtain a crude boride product; S3, stirring the crude boride product obtained in step S2 with the organic mixed solution, and then extracting, filtering, drying, rotary evaporating, and column chromatography to obtain a chiral boron compound; The structural formula of the α, β, γ, δ-unsaturated compound is The chiral boron compound has the structural formula: Wherein R1 is phenyl or p-fluorophenyl; R2 is phenyl, p-bromophenyl or styryl; the amine chiral ligand is a chiral bipyridine ligand, and the structural formula is 5. The use of a mesoporous cuprous oxide material in catalyzing chiral boron addition reaction according to claim 4, characterized in that: The solvent in step S1 is a mixed solvent of toluene and water, and the volume ratio of toluene to water is (1-9):(9-1).

6. The use of a mesoporous cuprous oxide material in catalyzing chiral boron addition reaction according to claim 4, characterized in that: The molar ratio of the α, β, γ, δ-unsaturated compound, the bipyraclostrobin, the mesoporous cuprous oxide catalyst, and the amine chiral ligand in step S1 is 1:(1.2-2.0):(0.03-0.09):(0.03-0.09); the stirring reaction is carried out at room temperature for 3-12 hours.

7. The use of a mesoporous cuprous oxide material in catalyzing chiral boron addition reaction according to claim 4, characterized in that: The extractant in step S2 is ethyl acetate; the desiccant is anhydrous sodium sulfate.

8. The use of a mesoporous cuprous oxide material in catalyzing chiral boron addition reaction according to claim 4, characterized in that: The organic mixed solution in step S3 includes NaBO3·4H2O, THF and deionized water, wherein the amount of NaBO3·4H2O is 367.0 mg, the amount of THF is 4.5 mL, and the amount of water is 3.0 mL.

9. The use of a mesoporous cuprous oxide material in catalyzing chiral boron addition reaction according to claim 8, characterized in that: The reaction condition in step S3 is stirring at room temperature for 3-6 hours.

10. The use of a mesoporous cuprous oxide material in catalyzing chiral boron addition reaction according to claim 9, characterized in that: The extractant in step S3 is ethyl acetate, and the desiccant is anhydrous sodium sulfate.

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