Synthesis method of 1, 3-diboron compound

Abstract

The invention belongs to the technical field of synthesis of diboron compounds, and particularly relates to a synthesis method of a 1, 3-diboron compound. Comprising the following steps: by taking an olefin compound, bis (pinacol) diborate and iodomethylene borate as raw materials, carrying out olefin carbon boronation reaction in a reaction system consisting of a Cu-based catalyst, sodium ethoxide and a solvent under a protective atmosphere to obtain the 1, 3-diboron compound. The invention provides a copper-catalyzed olefin boron alkylation strategy, iodomethylene borate is used as an electrophilic reagent, a series of racemic 1, 3-diboron compounds are constructed at excellent yield through a Cu-catalyzed olefin carbon boronation reaction, and an effective modularized synthesis method of the 1, 3-diboron compounds is realized. The reaction has the characteristics of mild reaction conditions, wide raw material sources, simple reaction process and high yield.

Description

Technical Field

[0001] The present invention belongs to the technical field of the synthesis of diboron compounds, and particularly relates to a method for synthesizing 1,3-diboron compounds. Background Art

[0002] Boric acid, boronic esters, etc. are powerful tools for constructing carbon-carbon bonds. They can not only undergo Suzuki-Miyaura coupling reactions with halogenated hydrocarbons under palladium catalysis, but also undergo Chan-Lam coupling reactions with compounds containing nitrogen-hydrogen bonds or oxygen-hydrogen bonds under copper catalysis. Boronic ester functional groups (such as Bpin) can undergo stereospecific transformations in reactions, such as stereoselectively undergoing oxidation reactions, amination reactions, halogenation reactions, Matteson homologation reactions, Zweifel alkenylation reactions, alkynylation reactions, deborohydration reactions, etc. to obtain compounds containing functional groups such as hydroxyl groups, amino groups, halogens, alkenyl groups, and alkynyl groups. This characteristic makes them widely used in the construction of natural products and pharmaceutical intermediates.

[0003] In the field of synthetic chemistry, diboron compounds have attracted extensive attention due to their unique synthetic value. Multiple catalytic couplings and chemical transformations can be selectively carried out on them, providing an effective way for the synthesis of more refined and structurally complex drug molecules. Currently, many commercially available drug molecules contain chiral 1,3-bifunctional group structures, such as rosuvastatin for the treatment of hypercholesterolemia, aliskiren for the treatment of hypertension, and sacubitril for the treatment of heart failure. Such drug molecules can be stereospecifically prepared through chiral 1,3-diboron compounds, which can improve the convenience of their synthesis.

[0004] However, the synthesis methods of 1,3-diboron compounds are still relatively limited. For example, in 2016, the Aggarwal research group obtained 1,2-diboron compounds through the Morken / Nishiyama diboration reaction. It reacted with enantiomerically enriched lithiated carbamates and underwent a 1,2-boron migration process to regioselectively and stereoselectively prepare chiral 1,3-diboron compounds. The synthetic route is as follows: .

[0005] In 2017, based on the homologation reaction of diboron compounds, the Aggarwal research group reported a method using geminal diboron reagents as raw materials. Based on the 1,2-boron migration process, chiral 1,2- and 1,3-diboron compounds were respectively prepared through different lithium reagents. The synthetic route is as follows: .

[0006] In 2020, the Studer research group synthesized a series of racemic 1,3-diboronic compounds based on the twice 1,2-alkyl / aryl migration process of easily prepared vinyl boronic esters and commercially available iodomethylidene boronic esters under the action of lithium reagents. The synthetic route is as follows: 。

[0007] However, the construction of chiral 1,3-diboronic compounds still depends on the homology of 1,1- or 1,2-diborates. These transformations require the pre-synthesis of chiral diborates or the preparation of stoichiometric air- and humidity-sensitive chiral organolithium reagents, which have cumbersome synthesis steps and high requirements for reaction conditions. Modular and practical synthesis remains a challenge. Summary of the Invention

[0008] To solve the above problems, the present invention provides a method for synthesizing 1,3-diboronic compounds, providing a copper-catalyzed borylation strategy for olefins. Using iodomethylidene boronic ester as an electrophilic reagent, through the Cu-catalyzed carboboration reaction of olefins, a series of racemic 1,3-diboronic compounds are constructed with excellent yields, realizing an effective modular synthesis method for 1,3-diboronic compounds. This reaction synthesizes 1,3-diboronic compounds widely and efficiently under simple and mild reaction conditions, with a simple reaction process and high yields.

[0009] The present invention solves the above technical problems through the following technical solutions.

[0010] The object of the present invention is to provide a method for synthesizing 1,3-diboronic compounds, including the following steps: Using an olefin compound, bis(pinacolato)diboron, and iodomethylidene boronic ester as raw materials, in a reaction system composed of a Cu-based catalyst, sodium ethoxide, and a solvent, under a protective atmosphere, an olefin carboboration reaction is carried out to obtain 1,3-diboronic compounds.

[0011] Further, the molar ratio of the olefin compound, bis(pinacolato)diboron, and iodomethylidene boronic ester is 1:1-1.5:1-1.5.

[0012] Further, the molar ratio of the Cu-based catalyst, sodium ethoxide, and the olefin compound is 0.08-0.15:4:2.

[0013] Further, the Cu-based catalyst is a N-heterocyclic carbene copper complex.

[0014] Further, the iodomethylidene boronic ester is pinacolyl iodomethyl boronate or 2-iodomethyl-4,4,5,5-tetraethyl-1,3,2-dioxaborolane.

[0015] Further, the solvent is 1,4-dioxane, tetrahydrofuran, chlorobenzene or toluene.

[0016] Further, the temperature of the olefin carboboration reaction is room temperature, and the reaction time is 10 h to 15 h.

[0017] Further, the structural formula of the olefin compound is as follows: .

[0018] Wherein, R is phenyl, substituted phenyl, substituted indolyl, substituted pyridyl, thiophene, ethoxydimethylsilyl or dimethylphenylsilyl.

[0019] The substituents of phenyl are C1-C4 alkyl, C1-C3 alkoxy, R 1 COOR 2 , halogen, benzene, furan, pyrazole, diketone compounds, benzo-fused ring compounds, naphthalene derivatives, aromatic ketone compounds, oxygen-containing heterocyclic compounds; R 1 is C1-C3 alkyl, R 2 is C1-C4 alkyl.

[0020] The substituents of indolyl are R 3 COOR 4 , R 3 is C1-C3 alkyl, R 4 is C1-C4 alkyl.

[0021] The substituents of pyridine are C1-C3 alkoxy.

[0022] Further, the substituents of phenyl are C3-C4 alkyl, C1-C2 alkoxy, R 1 COOR 2 , fluorine, chlorine, bromine, benzene, furan, pyrazole, isoindoline-1,3-dione, 2,2-difluorobenzodioxazole, 2-(6-methoxynaphthalen-2-yl)propanoic acid, 3-benzoylphenyl)propanoic acid, 5-(3,4,5-trimethoxyphenyl)-9-oxo-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one, 13-methyl-3-oxo-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one or 13-methyl-1-3-oxo)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl pentanoate; R 1 is C1-C2 alkyl, R 2 is C1-C2 alkyl.

[0023] The substituents of indolyl are R3 COOR 4 ,where R 3 is C1-C2 alkyl, and R 4 is C3-C4.

[0024] The substituent of pyridine is C1-C2 alkoxy.

[0025] Furthermore, the olefin compound is styrene, 4-tert-butylstyrene, 3,4-dimethoxystyrene, 3-methoxystyrene, 4-vinylphenyl acetate, 2-bromo-4,5-dimethoxystyrene, 4-fluorostyrene, 4-chlorostyrene, 4-phenylstyrene, tert-butyl 5-vinyl-1H-indole-1-carboxylate, 5-vinylbenzofuran, 1-(4-vinylphenyl)-1H-pyrazole, 2-(4-vinylbenzyl)isoindoline-1,3-dione, 2,2-difluoro-5-vinyl d [1,3]benzodioxole, 2-methoxy-5-vinylpyridine, 2-vinylnaphthalene, 1,4-dihydro-1,4-epoxynaphthalene, 3-vinylthiophene, 2-(ethoxydimethylsilyl)ethylene, 2-(dimethylphenylsilyl)ethylene, 1-phenyl-1,3-butadiene, 4-vinylbenzyl 2-(6-methoxynaphthalen-2-yl)propionate, (5 R ,9 R )-5-(3,4,5-trimethoxyphenyl)-9-((4-vinylbenzyl)oxy)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3- d [1,3]dioxol-6(5aH)-one, (8 R ,9 S ,13 S ,14 S )-13-methyl-3-((4-vinylbenzyl)oxy)-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one, 4-vinylbenzyl 2-(3-benzoylphenyl)propionate or (8 R ,9 S ,13 S ,14 S )-13-methyll-3-((4-vinylbenzyl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl pentanoate.

[0026] The present invention has the following beneficial effects compared with the prior art: The present invention provides a method for synthesizing 1,3-diboron compounds, providing an asymmetric borylation strategy for copper-catalyzed alkenes. Using simple and readily available alkene compounds, bis(pinacolato)diboron, and iodomethyl boronic acid ester as starting materials, and using iodoalkyl borate as an electrophile, through the Cu-catalyzed carboboration reaction of alkenes, first sodium ethoxide, a copper catalyst, and bis(pinacolato)diboron react to form copper boride, and then through the Cu-catalyzed carboboration reaction of alkenes, it is added to the alkene to obtain a β-borylcopper complex intermediate, which reacts with a halogenated hydrocarbon, and after reductive elimination, the desired final product is formed, and the active Cu catalyst is regenerated, realizing an effective modular synthesis method for 1,3-diboron compounds, constructing a series of racemic 1,3-diboron compounds in excellent yields. This reaction synthesizes 1,3-diboron compounds widely and efficiently under simple and mild reaction conditions, the reaction process is simple and the yield is high, and it overcomes the limitations such as harsh reaction conditions of high temperature and strong base, limited scope of complex substrate synthesis, and the use of relatively expensive photocatalysts.

[0027] The 1,3-diboron compounds prepared by the present invention can not only be scaled up to the gram scale, but also can be used to prepare 1,3-difunctional compounds through reactions such as oxidation and amination. In addition, the product can also be used to prepare 1,5-difunctional compounds through carbon-carbon bond formation reactions. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 1H NMR spectrum of 2,2'-(2-phenylpropane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) prepared in Example 1 of the present invention 1 1H NMR spectrum.

[0029] Figure 2 13C NMR spectrum of 2,2'-(2-phenylpropane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) prepared in Example 1 of the present invention 13 13C NMR spectrum. DETAILED DESCRIPTION OF THE INVENTION

[0030] The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative efforts shall fall within the protection scope of the present invention.

[0031] The present invention provides a method for synthesizing 1,3-diboron compounds, comprising the following steps: Using an olefin compound, bis(pinacolato)diboron, and iodomethylboronic acid pinacol ester as raw materials, in a reaction system composed of a Cu-based catalyst, sodium ethoxide, and a solvent, an olefin carboboration reaction is carried out under a protective atmosphere to obtain a 1,3-diboron compound; the synthetic route is as follows: 。

[0032] The present invention provides a copper-catalyzed asymmetric borylation strategy for olefins. Based on a copper-catalyzed dual-functional group strategy, using simple and readily available olefin compounds, bis(pinacolato)diboron, and iodomethylboronic acid pinacol ester as starting materials, and using iodoalkyl borate as an electrophile, through a Cu-catalyzed olefin carboboration reaction, the reaction mechanism is as follows: 。

[0033] First, sodium ethoxide, a copper catalyst, and bis(pinacolato)diboron react to form copper boride, which is then added to the olefin through a Cu-catalyzed olefin carboboration reaction to obtain a β-borylcopper complex intermediate. This intermediate reacts with a halogenated hydrocarbon, and after reductive elimination, the desired final product is formed, and the active Cu catalyst is regenerated, realizing an effective modular synthesis method for 1,3-diboron compounds. A series of racemic 1,3-diboron compounds are constructed in excellent yields. This reaction synthesizes 1,3-diboron compounds widely and efficiently under simple and mild reaction conditions. The reaction process is simple and has a high yield, and it overcomes obstacles such as harsh reaction conditions like high temperature and strong base, limited scope of complex substrate synthesis, and the use of relatively expensive photocatalysts.

[0034] In a specific embodiment, the Cu-based catalyst is a N-heterocyclic carbene copper complex. The chemical formula of the N-heterocyclic carbene copper complex is SIMesCuCl, and the structural formula is as follows:

[0035] 。

[0036] The following is further illustrated by specific examples.

[0037] Example 1 A method for synthesizing a 1,3-diboron compound, where the 1,3-diboron compound is 2,2'-(2-phenylpropane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4a), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes. Then, sequentially add N-heterocyclic carbene copper complex SIMesCuCl (0.01 mmol, 5 mol %), sodium ethoxide (EtONa, 0.4 mmol, 2.0 equiv.), bis(pinacolato)diboron 2a (B 2 pin2 , 0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then styrene 1a (0.2 mmol, 1.0 equiv.) and pinacol iodomethylboronate 3a (0.3 mmol, 1.5 equiv.) were added to the reaction system; the reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4a. Compound 4a was a colorless oil with a yield of 81%. The synthetic route is as follows:

[0038] .

[0039] Compound 4a was characterized, 1 H NMR (400 MHz, CDCl 3 ) was as Figure 1 shown, 13 C NMR (400 MHz, CDCl 3 ) spectrum was as Figure 2 shown. It could be seen from Figure 1 and Figure 2 that compound 4a was successfully synthesized.

[0040] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.22 (dt, J J = 14.9, 7.3 Hz, 4H), 7.09 (t, J J = 7.1 Hz, 1H), 3.15 (p, J J = 7.8 Hz, 1H), 1.20 (dd, J J = 7.9, 4.9 Hz, 4H), 1.07 (d, J J = 2.4 Hz, 24H).

[0041] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 148.9, 128.0 (2C), 127.3 (2C), 125.7, 82.9 (4C), 37.5, 24.8 (4C), 24.7 (4C), 22.4 (2C).

[0042] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 21 H 34 B 2 O 4[M+Na] + 395.25354; Measured value: 395.25446.

[0043] Example 2 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 2,2'-(2-(4-(tert-butyl)phenyl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4b), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 4-tert-butylstyrene 1b (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4b. Compound 4b is a foamy solid with a yield of 82%. The synthetic route is as follows:

[0044] 。

[0045] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.24 – 7.20 (m, 2H), 7.17 (d, J J = 8.4 Hz, 2H), 3.12 (ddd, J J = 15.8, 8.7, 7.1 Hz, 1H), 1.25 (s, 9H), 1.22 – 1.16(m, 4H), 1.06 (d, J J = 4.1 Hz, 24H).

[0046] 13C NMR characterization: 1313C NMR (100 MHz, CDCl3) δ 147.7, 145.2, 126.2 (2C), 124.1 (2C), 82.1 (4C), 36.3, 33.6, 30.8 (3C), 24.1 (4C), 24.0 (4C), 21.7 (2C).

[0047] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 25 H 42 B 2 O 4 [M+Na] + 451.31614; measured value: 451.31653.

[0048] Example 3 A synthesis method of a 1,3-diboron compound, the 1,3-diboron compound being 2,2'-(2-(3,4-dimethoxycyclohex-1,5-dien-1-yl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4c), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M), stir at room temperature for about 15 minutes, then add 3,4-dimethoxystyrene 1c (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4c. Compound 4c is a foamy solid with a yield of 80%. The synthetic route is as follows:

[0049] .

[0050] 1H NMR characterization: 1 1H NMR (400 MHz, CDCl 3 ) δ 6.83 – 6.76 (m, 2H), 6.73 (d, J J = 8.2 Hz, 1H), 3.83 (d, J= 14.6 Hz, 6H), 1.17 (dd, J = 7.9, 4.0 Hz, 4H), 1.08 (d, J = 3.4 Hz, 24H).

[0051] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 148.2, 146.8, 141.9, 118.9, 110.9, 110.8, 82.9 (4C), 56.0, 55.7, 37.1, 24.8 (4C), 24.8 (4C), 22.7 (2C).

[0052] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 23 H 40 B 2 O 6 [M + H] + 435.30838; measured value: 435.30659.

[0053] Example 4 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 2-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)-3-methoxyphenol (Compound 4d), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 3-methoxystyrene 1d (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4d. Compound 4d is a foamy solid with a yield of 71%. The synthetic route is as follows:

[0054] .

[0055] 1H NMR characterization: 11H NMR (400 MHz, CDCl 3 ) δ 7.18 (d, J J = 8.9 Hz, 1H), 6.82(d, J J = 3.0 Hz, 1H), 6.61 (dd, J J = 8.8, 3.1 Hz, 1H), 5.62 (s, 1H), 3.74 (s, 3H),3.56 (p, J J = 7.9 Hz, 1H), 1.25 – 1.20 (m, 4H), 1.08 (d, J J = 14.2 Hz, 24H).

[0056] 13C NMR characterization: 13 13C NMR (100 MHz, CDCl 3 ) δ 154.8, 149.2, 139.6, 117.8,113.0, 111.8, 82.8 (4C), 55.7, 30.5, 24.8 (4C), 24.7 (4C), 20.6 (2C).

[0057] Example 5 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)phenyl acetate (Compound 4e), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 4-vinylphenyl acetate 1e (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4e. Compound 4e is a colorless oil with a yield of 72%. The synthetic route is as follows:

[0058] .

[0059] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3) δ 7.25 (dd, J J = 8.3, 1.8 Hz, 2H), 6.94 – 6.88 (m, 2H), 3.16 (tt, J J = 8.9, 6.9 Hz, 1H), 2.25 (s, 3H), 1.19 (d, J J = 7.2 Hz, 3H), 1.16 (s, 1H), 1.08 (d, J J = 3.9 Hz, 24H).

[0060] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 169.6, 148.7, 146.5, 128.2(2C), 120.9 (2C), 83.0(4C), 36.9, 24.8 (4C), 24.7 (4C), 22.5 (2C), 21.2.

[0061] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 23 H 36 B 2 O 6 [M+H] + 431.27708; measured value: 431.27688.

[0062] Example 6 A method for synthesizing a 1,3-diboronic compound, the 1,3-diboronic compound being 2,2'-(2-(2-bromo-4,5-dimethoxyphenyl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4f), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 ml reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 22a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then 2-bromo-4,5-dimethoxystyrene 1f (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) were added to the reaction system; the reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4f, which was a colorless oil with a yield of 70%. The synthetic route is as follows:

[0063] 。

[0064] Characterization by 1H NMR: 1 H NMR (400 MHz, CDCl 3 ) δ 6.92 (s, 1H), 6.85 (s, 1H), 3.84 (s, 3H), 3.80 (s, 3H), 3.54 (p, J = 7.7 Hz, 1H), 1.19 (dd, J = 7.8, 2.1 Hz, 4H), 1.10 (s, 12H), 1.07 (s, 12H).

[0065] Characterization by 13C NMR: 13 C NMR (100 MHz, CDCl 3 ) δ 148.2, 147.3, 139.9, 115.2, 113.8, 110.8, 82.9 (4C), 56.2, 55.9, 35.6, 24.9 (4C), 24.7 (4C), 20.6 (2C).

[0066] Example 7 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 2,2'-(2-(4-fluorophenyl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4g), comprising the following steps: Under a nitrogen atmosphere in a glove box, in a 10 mL reaction tube, add and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 22a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then 1 g (0.2 mmol, 1.0 equiv.) of 4-fluorostyrene and 3a (0.3 mmol, 1.5 equiv.) of pinacol iodomethylborate were added to the reaction system; the reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4g, which was a foamy solid with a yield of 70%. The synthetic route is as follows:

[0067] .

[0068] Characterization by 1H NMR: 1 H NMR (400 MHz, CDCl 3 ) δ 7.23 – 7.18 (m, 2H), 6.92 – 6.85 (m, 2H), 3.14 (tt, J J = 9.1, 6.7 Hz, 1H), 1.20 – 1.12 (m, 4H), 1.07 (d, J J = 3.7 Hz, 24H).

[0069] Characterization by 13C NMR: 13 C NMR (100 MHz, CDCl 3 ) δ 162.4, 160.0, 144.6, 144.6, 128.7, 128.6, 114.6, 114.4, 82.9 (4C), 36.8, 24.8 (4C), 24.7 (4C), 22.7 (2C).

[0070] Characterization by mass spectrometry: HRMS m / z (ESI) calculated value: C 21 H 33 B 2 FO 4 [M+K] + 429.21806; measured value: 429.21769.

[0071] Example 8 A method for synthesizing a 1,3-diboronic compound, the 1,3-diboronic compound being 2,2'-(2-(4-chlorophenyl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4h), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes. Then, successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes. Then, add 4-chlorostyrene 1h (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4h. Compound 4h is a foamy solid with a yield of 66%. The synthetic route is as follows:

[0072] 。

[0073] Characterization by 1H NMR: 1 H NMR (400 MHz, CDCl 3 ) δ 7.18 (s, 4H), 3.13 (tt, J J = 8.8, 6.7 Hz, 1H), 1.20 – 1.14 (m, 4H), 1.08 (d, J J = 4.8 Hz, 24H).

[0074] Characterization by 13C NMR: 13 C NMR (100 MHz, CDCl 3 ) δ 147.5, 131.1, 128.7 (2C), 128.0 (2C), 83.0 (4C), 36.9, 24.8 (4C), 24.7 (4C), 21.8 (2C).

[0075] Example 9 A method for synthesizing a 1,3-diboronic compound, the 1,3-diboronic compound being 2,2'-(2-([1,1'-biphenyl]-4-yl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4i), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes. Then, successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then 4-phenylstyrene 1i (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) were added to the reaction system; the reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4i, which was a foamy solid with a yield of 82%. The synthetic route is as follows:

[0076] 。

[0077] Characterization by 1H NMR: 1 H NMR (400 MHz, CDCl 3 ) δ 7.6 – 7.5 (m, 2H), 7.5 – 7.5(m, 2H), 7.4 (dd, J J = 8.3, 6.8 Hz, 2H), 7.4 – 7.3 (m, 3H), 3.3 – 3.2 (m, 1H), 1.3 – 1.2 (m, 4H), 1.1 (s, 24H).

[0078] Characterization by 13C NMR: 13 C NMR (100 MHz, CDCl 3 ) δ 148.2, 141.6, 138.5, 128.7(2C), 127.7 (2C), 127.0 (2C), 126.9, 126.7 (2C), 82.9 (4C), 37.1, 24.8 (4C), 24.8 (4C), 22.4 (2C).

[0079] Characterization by mass spectrometry: HRMS m / z (ESI) calculated value: C 27 H 38 B 2 O 4 [M+Na] + 471.28484; measured value: 471.28517.

[0080] Example 10 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being tert-butyl-5-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)-1 H-Indole-1-carboxylate (Compound 4j), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes. Then, sequentially add SIMesCuCl (0.01 mmol, 5 mol%), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes. Then, add tert-butyl 5-vinyl-1H-indole-1-carboxylate 1j (0.2 mmol, 1.0 equiv.) and pinacol iodomethylboronate 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4j. Compound 4j is a colorless oil with a yield of 82%. The synthetic route is as follows:

[0081] .

[0082] Characterization by 1H NMR: 1 H NMR (400 MHz, CDCl 3 ) δ 7.55 – 7.51 (m, 2H), 7.45 –7.42 (m, 2H), 7.38 (dd, J J = 8.3, 6.8 Hz, 2H), 7.32 – 7.25 (m, 3H), 3.23 – 3.14(m, 1H), 1.21 (dd, J J = 6.3, 2.4 Hz, 4H), 1.06 (s, 24H).

[0083] Characterization by 13C NMR: 13 C NMR (100 MHz, CDCl 3 ) δ 143.5, 131.5, 130.4, 129.8,129.5, 125.5, 123.9, 119.1, 114.5, 83.0, 82.8 (4C), 37.2, 28.2 (3C), 24.8(4C), 24.6 (4C), 22.75 (2C).

[0084] Characterization by mass spectrometry: HRMS m / z (ESI) calculated value: C 28 H 43 B 2 NO 6[M+Na] + 534.31687; Measured value: 534.31758.

[0085] Example 11 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 2,2'-(2-(benzofuran-5-yl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4k), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 5-vinylbenzofuran 1k (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4k. Compound 4k is a colorless oil with a yield of 70%. The synthetic route is as follows:

[0086] .

[0087] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.54 (d, J J = 2.2 Hz, 1H), 7.47(d, J = 1.8 Hz, 1H), 7.34 (d, J J = 8.4 Hz, 1H), 7.21 (dd, J J = 8.5, 1.9 Hz, 1H),6.68 (d, J J = 2.0 Hz, 1H), 3.28 (ddd, J J = 15.7, 8.8, 7.0 Hz, 1H), 1.27 – 1.23 (m,4H), 1.04 (d, J = 1.4 Hz, 24H).

[0088] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3) δ 153.6, 144.8, 143.6, 127.0, 124.0, 119.3, 110.5, 106.6, 82.9 (4C), 37.4, 24.8 (4C), 24.7 (4C), 22.9 (2C).

[0089] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 23 H 34 B 2 O 5 [M + H] + 534.31687; measured value: 534.31758.

[0090] Example 12 A synthetic method of a 1,3-diboron compound, the 1,3-diboron compound is 1-(4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)phenyl)-1 H -pyrazole (Compound 4l), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 ml reaction tube and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 1-(4-vinylphenyl)-1 H -pyrazole 1l (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4l. Compound 4l is a colorless oil with a yield of 66%. The synthetic route is as follows:

[0091] .

[0092] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.87 (d, J J = 2.5 Hz, 1H), 7.69(d, J= 1.8 Hz, 1H), 7.57 – 7.51 (m, 2H), 7.36 – 7.32 (m, 2H), 6.43 (t, J = 2.2Hz, 1H), 3.26 – 3.16 (m, 1H), 1.21 (d, J = 5.0 Hz, 4H), 1.09 (d, J = 4.2 Hz,24H).

[0093] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 147.5, 140.7, 138.1, 128.3(2C), 126.8, 118.9 (2C), 107.3, 83.0 (4C), 36.9, 24.8 (4C), 24.7 (4C), 22.4(2C).

[0094] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 24 H 36 B 2 N 2 O 4 [M+H] + 439.29340; measured value: 439.29477.

[0095] Example 13 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 2-(4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)benzyl)isoindoline-1,3-dione (Compound 4m), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 22a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then 2-(4-vinylbenzyl)isoindoline-1,3-dione 1m (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) were added to the reaction system. The reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4m, which was a white solid with a yield of 85%. The synthetic route is as follows:

[0096] .

[0097] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (dd, J J = 5.5, 3.0 Hz, 2H),7.66 (dd, J J = 5.4, 3.1 Hz, 2H), 7.25 (d, J J = 8.2 Hz, 2H), 7.17 (d, J J = 8.2 Hz, 2H),4.76 (s, 2H), 3.09 (tt, J J = 8.8, 6.9 Hz, 1H), 1.18 – 1.08 (m, 4H), 1.01 (s,24H).

[0098] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 168.0 (2C), 148.7, 134.0 (2C),133.7, 132.3 (2C), 128.3 (2C), 127.6 (2C), 123.3 (2C), 82.9 (4C), 41.5, 37.1,24.7 (4C), 24.7 (4C), 22.3 (2C).

[0099] HRMS characterization: HRMS m / z (ESI) Calcd for C 30 H 39 B 2 NO 6 [M+Na] + 554.28557; Found: 554.28621.

[0100] Example 14 A method for synthesizing a 1,3-diboron compound, where the 1,3-diboron compound is 2-(4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)benzyl)isoindoline-1,3-dione (Compound 4n), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes. Then, sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M). Stir at room temperature for about 15 minutes. Then, add 2,2-difluoro-5-vinyl d [1,3]benzodioxole 1n (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; Stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4n. Compound 4n is a colorless oil with a yield of 54%. The synthetic route is as follows:

[0101] .

[0102] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.0 (s, 1H), 7.0 (dd, J = 8.3, 1.7 Hz, 1H), 6.9 (d, J = 8.2 Hz, 1H), 3.2 (tt, J = 9.0, 6.6 Hz, 1H), 1.2 (dd, J = 14.9, 7.7 Hz, 4H), 1.1 (d, J = 4.2 Hz, 24H).

[0103] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 145.4, 143.5, 141.7, 131.7, 122.1, 108.8, 108.6, 83.1 (4C), 37.4, 24.8 (4C), 24.7 (4C), 22.7 (2C).

[0104] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 22 H 32 B 2 F 2 O 6 [M+NH 4 + 470.26913; measured value: 470.27325.

[0105] Example 15 A method for synthesizing a 1,3-diboronic compound, the 1,3-diboronic compound being 5-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)-2-methoxypyridine (Compound 4o), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M), stir at room temperature for about 15 minutes, then add 2-methoxy-5-vinylpyridine 1o (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4o. Compound 4o is a colorless oil with a yield of 81%. The synthetic route is as follows:

[0106] .

[0107] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 8.02 (d, J = 2.4 Hz, 1H), 7.48(dd, J = 8.5, 2.5 Hz, 1H), 6.62 (d, J = 8.5 Hz, 1H), 3.86 (s, 3H), 3.11 (tt, J =9.0, 6.5 Hz, 1H), 1.19 – 1.11 (m, 4H), 1.08 (d, J = 3.0 Hz, 24H).​

[0108] Characterization by carbon-13 nuclear magnetic resonance spectroscopy: 13 C NMR (100 MHz, CDCl 3 ) δ 162.5, 145.6, 137.6, 136.8, 110.1, 83.0 (4C), 53.4, 34.0, 24.8 (4C), 24.7 (4C), 22.0 (2C).

[0109] Characterization by mass spectrometry: Calculated HRMS m / z (ESI) for C 21 H 35 B 2 NO 5 [M+H] + 404.27741; Measured value: 404.27784.

[0110] Example 16 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 2,2'-(2-(naphthalen-2-yl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4p), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 2-vinylnaphthalene 1p (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4p. Compound 4p is a pale yellow solid with a yield of 74%. The synthetic route is as follows:

[0111] .

[0112] Characterization by proton nuclear magnetic resonance spectroscopy: 1 H NMR (400 MHz, CDCl 3 ) δ 7.77 – 7.66 (m, 4H), 7.46 – 7.42 (m, 1H), 7.41 – 7.35 (m, 2H), 3.35 (p,J = 7.8 Hz, 1H), 1.30 (d, J = 7.1 Hz, 4H), 1.04 (d, J = 2.4 Hz, 24H).

[0113] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 146.5, 133.6, 132.2, 127.7, 127.6, 127.6, 126.3, 125.5, 125.3, 124.8, 82.9 (4C), 37.5, 24.8 (4C), 24.7 (4C), 22.0 (2C).

[0114] MS characterization: HRMS m / z (ESI) calculated value: C 21 H 35 B 2 NO 5 [M+Na] + 445.26919; measured value: 445.27077.

[0115] Example 17 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 4,4,5,5-tetramethyl-2-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)methyl)-1,3,2-dioxaborolane (Compound 4q), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M), stir at room temperature for about 15 minutes, then add 1,4-dihydro-1,4-epoxynaphthalene 1q (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4q. Compound 4q is a colorless oil with a yield of 61%. The synthetic route is as follows:

[0116] 。

[0117] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.22 (dd, J J = 5.6, 2.7 Hz, 1H),7.19 – 7.15 (m, 1H), 7.11 – 7.08 (m, 2H), 5.40 (s, 1H), 5.03 (s, 1H), 2.13(ddd, J J = 11.0, 9.0, 5.0 Hz, 1H), 1.30 – 1.27 (m, 18H), 1.27 (s, 6H), 1.24 –1.19 (m, 2H), 1.06 (dd, J J = 16.1, 11.2 Hz, 1H).

[0118] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 147.2, 145.9, 126.3, 126.0,119.0, 118.2, 85.4, 83.6 (2C), 83.1 (2C), 81.3, 39.1, 25.2 (2C), 25.1 (2C),25.0 (2C), 24.9 (2C). The carbon atom connected to boron is shielded.

[0119] MS characterization: HRMS m / z (ESI) calculated value: C 23 H 34 B 2 O 5 [M+Na] + 435.24846; measured value: 435.24978.

[0120] Example 18 A synthesis method of a 1,3-diboron compound, the 1,3-diboron compound being 2,2'-(2-(thiophen-3-yl)propane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4r), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then 3-vinylthiophene 1r (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) were added to the reaction system; the reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4r. Compound 4r was a colorless oil with a yield of 63%. The synthetic route is as follows:

[0121] 。

[0122] Characterization by 1H NMR: 1 H NMR (400 MHz, CDCl 3 ) δ 7.13 (dd, J J = 5.0, 3.0 Hz, 1H), 7.01 (dd, J J = 5.0, 1.3 Hz, 1H), 6.95 (dd, J J = 3.0, 1.3 Hz, 1H), 3.29 (p, J J = 7.7Hz, 1H), 1.18 (d, J J = 8.1 Hz, 4H), 1.11 (d, J = 3.3 Hz, 24H).

[0123] Characterization by 13C NMR: 13 C NMR (100 MHz, CDCl 3 ) δ 150.0, 127.3, 124.6, 119.1, 82.9 (4C), 32.8, 24.8 (4C), 24.8 (4C), 22.0 (2C).

[0124] Characterization by mass spectrometry: HRMS m / z (ESI) calculated value: C 19 H 32 B 2 O 4 S [M+Na] + 401.20996; measured value: 401.21376.

[0125] Example 19 A method for synthesizing a 1,3-diboron compound, where the 1,3-diboron compound is (1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)(ethoxy)dimethylsilane (Compound 4s), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes. Then, sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes. Then, add 2-(ethoxydimethylsilyl)ethylene 1s (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4s. Compound 4s is a colorless oil with a yield of 70%. The synthetic route is as follows:

[0126] 。

[0127] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 3.65 (q, J J = 7.1 Hz, 2H), 1.22 (d, J J = 2.0 Hz, 24H), 1.15 (t, J J = 7.0 Hz, 3H), 0.96 (dd, J J = 16.1, 7.3 Hz, 2H), 0.77 (dd, J J = 16.0, 7.2 Hz, 2H), 0.06 (s, 6H).

[0128] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 83.4 (2C), 82.9 (2C), 58.4, 25.1 (2C), 25.0 (2C), 24.9 (2C), 24.8 (2C), 18.7, 18.5, 17.3, 15.8, -1.8, -3.5.

[0129] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 19 H 40 B 2 O 5 Si [M+NH 4 + 374.36075; measured value: 374.36277.

[0130] Example 20 A synthesis method of a 1,3-diboron compound, the 1,3-diboron compound being 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)dimethyl(phenyl)silane (Compound 4t), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 2-(dimethylphenylsilyl)ethylene 1t (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4t. Compound 4t is a colorless oil with a yield of 82%. The synthesis route is as follows:

[0131] .

[0132] 1H NMR characterization: 1 1H NMR (400 MHz, CDCl 3 ) δ 7.54 – 7.50 (m, 2H), 7.32 –7.27 (m, 3H), 1.19 (d, J = 4.1 Hz, 24H), 0.96 (dd, J = 16.2, 6.9 Hz, 2H), 0.76(dd, J = 16.2, 7.5 Hz, 2H), 0.25 (s, 6H).

[0133] 13C NMR characterization: 13 13C NMR (100 MHz, CDCl​3 ) δ 138.9, 134.4 (2C), 128.7, 127.6 (2C), 82.9 (4C), 25.1 (4C), 24.7 (4C), 15.0, -4.4 (2C). The carbon atoms connected to boron are shielded.

[0134] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 23 H 40 B 2 O 4 Si [M+Na] + 453.27742; measured value: 453.27884.

[0135] Example 21 A synthetic method of a 1,3-diboron compound, the 1,3-diboron compound being ( E )-2,2'-(2-styrylpropane-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (Compound 4u), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add 1-phenyl-1,3-butadiene 1u (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4u. Compound 4u is a colorless oil with a yield of 47%. The synthetic route is as follows:

[0136] .

[0137] 1H NMR characterization: 1 1H NMR (400 MHz, CDCl 3 ) δ 7.30 (td, J J = 8.2, 7.8, 2.2 Hz, 3H), 7.18 – 7.13 (m, 2H), 6.36 (d, J= 15.9 Hz, 1H), 6.21 (dd, J = 15.9, 8.0 Hz,1H), 2.82 – 2.72 (m, 1H), 1.20 (s, 24H), 1.17 (d, J = 5.3 Hz, 4H)。

[0138] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 137.6, 137.3, 127.8(2C),126.8, 126.0, 125.5(2C), 82.4(4C), 34.5, 24.4(4C), 24.2(4C). The carbon atoms connected to boron are shielded.

[0139] MS characterization: HRMS m / z (ESI) calculated value: C 23 H 36 B 2 O 4 [M+Na] + 421.26919; measured value: 421.27088.

[0140] Example 22 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 4,4,5,5-tetraethyl-2-(2-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-1,3,2-dioxaborolane (Compound 4v), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add styrene 1a (0.2 mmol, 1.0 equiv.) and 2-iodomethyl-4,4,5,5-tetraethyl-1,3,2-dioxaborolane 3a' (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4v. Compound 4v is a colorless oil with a yield of 72%. The synthesis route is as follows:

[0141] .

[0142] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.3 – 7.2 (m, 2H), 7.2 – 7.2(m, 2H), 7.1 – 7.0 (m, 1H), 3.2 – 3.1 (m, 1H), 1.5 (qd, J J = 7.4, 2.0 Hz, 8H),1.2 – 1.2 (m, 4H), 1.1 (s, 12H), 0.8 (td, J J = 7.5, 1.3 Hz, 12H).

[0143] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 149.0, 127.8 (2C), 127.2 (2C),125.5, 87.9 (2C), 82.8 (2C), 37.3, 26.2 (2C), 26.1 (2C), 24.7 (2C), 24.7(2C), 8.7 (2C), 8.7 (2C). The carbon atoms connected to boron are shielded.

[0144] MS characterization: HRMS m / z (ESI) calculated value: C 25 H 42 B 2 O 4 [M+Na] + 451.31614; measured value: 451.31653.

[0145] Example 23 A synthesis method of a 1,3-diboron compound, the 1,3-diboron compound is 4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)benzyl( S )-2-(6-methoxynaphthalen-2-yl)propanoic acid (Compound 4w), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 22a (0.24 mmol, 1.2 equiv.) and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then 2-(6-methoxynaphthalen-2-yl)propanoic acid 4-vinylbenzyl ester 1w (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) were added to the reaction system; the reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4w, which was a white solid with a yield of 72%. The synthetic route is as follows:

[0146] 。

[0147] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.70 – 7.63 (m, 3H), 7.39 (dd, J J = 8.5, 1.9 Hz, 1H), 7.19 (d, J J = 8.0 Hz, 2H), 7.15 – 7.09 (m, 4H), 5.10 – 4.96(m, 2H), 3.91 (s, 3H), 3.18 – 3.09 (m, 1H), 1.56 (d, J J = 7.1 Hz, 3H), 1.22 –1.13 (m, 4H), 1.05 (d, J J = 3.7 Hz, 24H).

[0148] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 174.6, 157.7, 149.1, 135.7,133.8, 133.2, 129.4, 129.0, 127.9 (2C), 127.4 (2C), 127.2, 126.4, 126.1,119.0, 105.6, 82.9 (4C), 66.7, 55.4, 45.6, 37.2, 24.8 (4C), 24.7 (4C), 22.3(2C), 18.7.

[0149] HRMS characterization: HRMS m / z (ESI) Calcd for C 25 H 42 B 2 O 4 [M+Na] +637.34784; Measured value: 637.35013.

[0150] Example 24 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being (5 R ,5 aR ,8 aR ,9 R )-9-((4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)benzyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-6(5 aH )-one (Compound 4x), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then successively add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.) and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add (5 R ,9 R )-5-(3,4,5-trimethoxyphenyl)-9-((4-vinylbenzyl)oxy)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3- d [1,3]dioxole-6(5 aH )-one 1x (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) to the reaction system; stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired compound 4x. Compound 4x is a white solid with a yield of 76%. The synthetic route is as follows:

[0151] .

[0152] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.3 (d, J= 8.1 Hz, 2H), 7.2 –7.2 (m, 2H), 6.9 (s, 1H), 6.5 (s, 2H), 6.4 (s, 1H), 5.9 (dd, J = 8.8, 1.5 Hz,2H), 4.7 (d, J = 11.5 Hz, 1H), 4.5 (d, J = 11.6 Hz, 1H), 4.4 (dd, J = 9.5, 7.0Hz, 1H), 4.3 (d, J = 7.0 Hz, 1H), 4.2 – 4.1 (m, 1H), 4.1 – 4.1 (m, 1H), 3.8 (s,3H), 3.8 (s, 6H), 3.2 – 3.2 (m, 2H), 2.9 (dtd, J = 10.2, 6.9, 3.4 Hz, 1H), 1.2(d, J = 8.5 Hz, 4H), 1.1 (d, J = 3.5 Hz, 24H).

[0153] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 178.3, 153.4 (2C), 149.4,147.6, 146.8, 138.9, 136.8, 134.5, 131.4, 129.5, 127.7 (2C), 127.6 (2C),109.6, 107.0, 105.6 (2C), 101.3, 83.0 (4C), 72.3, 70.1, 60.9, 60.5, 56.2(2C), 45.3, 44.9, 41.1, 37.1, 24.9, 24.8 (4C), 24.8 (4C), 22.3 (2C).

[0154] MS characterization: HRMS m / z (ESI) Calcd for C 44 H 56 B 2 O 12 [M+H] + 821.38501; Found 821.38783.

[0155] Example 25 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 8 R ,9S ,13 S ,14 S )-3-((4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)benzyl)oxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17 H -cyclopenta[a]phenanthren-17-one (Compound 4y), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.) and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add to the reaction system (8 R ,9 S ,13 S ,14 S )-13-methyl-3-((4-vinylbenzyl)oxy)-6,7,8,9,11,12,13,14,15,16-decahydro-17 H -cyclopenta[a]phenanthren-17-one 1y (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.); stir the reaction mixture at room temperature for 10 hours, and then purify the crude product by flash chromatography to obtain the desired Compound 4y. Compound 4y is a foamy solid with a yield of 68%. The synthetic route is as follows:

[0156] .

[0157] Characterization by 1H NMR: 1 H NMR (400 MHz, CDCl 3 ) δ 7.25 (s, 4H), 7.14 (dd, J J = 11.2, 8.4 Hz, 1H), 6.75 – 6.67 (m, 2H), 4.96 (s, 2H), 3.21 – 3.11 (m, 1H), 2.89 – 2.84 (m, 2H), 2.49 (dd, J J = 18.8, 8.6 Hz, 1H), 2.41 – 2.33 (m, 1H), 2.21 (d,J = 8.5 Hz, 1H), 2.18 – 2.10 (m, 1H), 2.09 – 2.02 (m, 1H), 1.95 (td, J = 9.9, 4.2Hz, 2H), 1.61 – 1.54 (m, 2H), 1.54 – 1.50 (m, 1H), 1.46 (t, J = 10.0 Hz, 3H),1.19 (t, J = 7.5 Hz, 4H), 1.07 (d, J = 3.0 Hz, 24H), 0.89 (s, 3H).

[0158] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3 ) δ 221.2, 157.0, 148.8, 137.7,134.5, 132.1, 127.4 (2C), 127.2 (2C), 126.3, 115.1, 112.5, 82.9 (4C), 70.0,50.5, 48.1, 44.1, 38.4, 37.2, 36.0, 31.7, 29.7, 26.6, 26.0, 24.8 (4C), 24.8(4C), 22.4 (2C), 21.7, 13.9.

[0159] MS characterization: HRMS m / z (ESI) calculated value: C 40 H 56 B 2 O 6 [M+Na] + 661.34784; measured value: 661.35036.

[0160] Example 26 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being 4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)benzyl 2-(3-benzoylphenyl) (Compound 4z), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 22a (0.24 mmol, 1.2 equiv.) and the solvent 1,4-dioxane (1.0 mL, 0.2 M) were stirred at room temperature for about 15 minutes, then 2-(3-benzoylphenyl)propanoic acid 4-vinylbenzyl ester 1z (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.) were added to the reaction system; the reaction mixture was stirred at room temperature for 10 hours, and then the crude product was purified by flash chromatography to obtain the desired compound 4z. Compound 4z was a foamy solid with a yield of 82%. The synthetic route is as follows:

[0161] 。

[0162] 1H NMR characterization: 1 H NMR (400 MHz, CDCl 3 ) δ 7.80 – 7.73 (m, 3H), 7.67 (dt, J J = 7.6, 1.5 Hz, 1H), 7.62 – 7.56 (m, 1H), 7.52 (dt, J J = 7.8, 1.6 Hz, 1H), 7.47(t, J J = 7.7 Hz, 2H), 7.42 (t, J J = 7.7 Hz, 1H), 7.21 (d, J J = 8.1 Hz, 2H), 7.12 (d, J J =8.1 Hz, 2H), 5.11 – 4.97 (m, 2H), 3.80 (q, J J = 7.2 Hz, 1H), 3.19 – 3.09 (m,1H), 1.52 (d, J J = 7.2 Hz, 3H), 1.21 – 1.13 (m, 4H), 1.06 (d, J J = 2.6 Hz, 24H).

[0163] 13C NMR characterization: 13 C NMR (100 MHz, CDCl 3) δ 196.6, 174.0, 149.3, 140.9, 138.0, 137.6, 133.0, 132.6, 131.6, 130.2 (2C), 129.4, 129.1, 128.6, 128.4 (2C), 127.9 (2C), 127.4 (2C), 82.9 (4C), 66.9, 45.5, 37.1, 24.8 (4C), 24.7 (4C), 22.3 (2C), 18.6。

[0164] Mass spectrometry characterization: HRMS m / z (ESI) calculated value: C 38 H 48 B 2 O 7 [M+Na] + 661.34784; measured value: 661.34976.

[0165] Example 26 A method for synthesizing a 1,3-diboron compound, the 1,3-diboron compound being (8 R ,9 S ,13 S ,14 S )-3-((4-(1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-2-yl)benzyl)oxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6 H -cyclopenta[a]phenanthren-17-yl pentanoate (Compound 4aa), comprising the following steps: Under a nitrogen atmosphere in a glove box, add to a 10 mL reaction tube and stir at room temperature for about 15 minutes, then sequentially add SIMesCuCl (0.01 mmol, 5 mol %), EtONa (0.4 mmol, 2.0 equiv.), B 2 pin 2 2a (0.24 mmol, 1.2 equiv.), and the solvent 1,4-dioxane (1.0 mL, 0.2 M) and stir at room temperature for about 15 minutes, then add (8 R ,9 S ,13 S ,14 S )-13-methyl 1-3-((4-vinylbenzyl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6 H-Cyclopenta[a]phenanthren-17-yl pentanoate 1aa (0.2 mmol, 1.0 equiv.) and iodomethylboronic acid pinacol ester 3a (0.3 mmol, 1.5 equiv.); The reaction mixture was stirred at room temperature for 10 h, and then the crude product was purified by flash chromatography to obtain the desired compound 4aa, which was a white solid with a yield of 63%. The synthetic route is as follows:

[0166] 。

[0167] Characterization by carbon-13 nuclear magnetic resonance: 13 C NMR (100 MHz, CDCl 3 ) δ 174.1, 156.9, 148.8, 137.9,134.5, 132.6, 127.4 (2C), 127.2 (2C), 126.3, 115.0, 112.4, 82.9 (4C), 82.5,69.9, 49.9, 43.9, 43.0, 38.7, 37.2, 37.0, 34.4, 29.9, 27.7, 27.3, 27.3, 26.3,24.8(4C), 24.7 (4C), 23.4 (2C), 22.4 (2C), 13.9, 12.2。

[0168] Characterization by mass spectrometry: HRMS m / z (ESI) calculated value: C 45 H 66 B 2 O 7 [M+Na] + 763.48869; measured value: 763.48665。

[0169] It should be noted that when the present invention involves a numerical range, it should be understood that both endpoints of each numerical range and any value between the two endpoints can be selected. Since the steps and methods adopted are the same as those in the examples, in order to prevent repetition, the present invention describes the preferred embodiments. Although the preferred embodiments of the present invention have been described, those skilled in the art can make additional changes and modifications to these embodiments once they know the basic creative concept. Therefore, the appended claims are intended to be interpreted as including the preferred embodiments and all changes and modifications falling within the scope of the present invention.

[0170] Obviously, those skilled in the art can make various changes and modifications to the present invention without departing from the spirit and scope of the present invention. Thus, if these modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalent technologies, the present invention is also intended to include these modifications and variations.

Claims

1. A method for synthesizing a 1,3-diboron compound, characterized in that: The following steps are involved: With olefin compounds, pinacol diborate and iodinated methylene borate as raw materials, olefin carboboration reaction is carried out in a reaction system consisting of a Cu-based catalyst, sodium ethoxide and a solvent under a protective atmosphere to obtain a 1,3-diboron compound.

2. The method for synthesizing a 1,3-diboron compound according to claim 1, characterized in that: The molar ratio of the olefin compound, the biboric acid pinacol ester and the iodinated methylene borate is 1:1-1.5:1-1.

5.

3. The method for synthesizing a 1,3-diboron compound according to claim 1, characterized in that: The molar ratio of the Cu-based catalyst, sodium ethoxide and olefin compound is 0.08-0.15:4:

2.

4. The method for synthesizing a 1,3-diboron compound according to claim 1, characterized in that: The Cu-based catalyst is a nitrogen heterocyclic carbene copper complex.

5. The method for synthesizing a 1,3-diboron compound according to claim 1, characterized in that: The iodinated methylene borate ester is iodinated methyl boric acid pinacol ester or 2-iodomethyl-4,4,5,5-tetraethyl-1,3,2-dioxaborolane.

6. The method for synthesizing a 1,3-diboron compound according to claim 1, characterized in that: The solvent is 1,4-dioxane, tetrahydrofuran, chlorobenzene or toluene.

7. The method for synthesizing a 1,3-diboron compound according to claim 1, characterized in that: The temperature of the olefin carboboration reaction is room temperature, and the reaction time is 10 h to 15 h.

8. The method for synthesizing a 1,3-diboron compound according to claim 1, characterized in that: The structural formula of the olefin compound is shown below: ； Wherein, R is phenyl, substituted phenyl, substituted indolyl, substituted pyridyl, thiophene, ethoxydimethylsilyl or dimethylphenylsilyl; The substituent of the phenyl group is C1-C4 alkyl, C1-C3 alkoxy, R1COOR2, halogen, benzene, furan, pyrazole, diketone compounds, benzo-fused ring compounds, naphthalene derivatives, aromatic ketone compounds, oxygen-containing heterocyclic compounds; R1 is C1-C3 alkyl, and R2 is C1-C4 alkyl; The substituent of the indolyl group is R3COOR4, R3 is a C1-C3 alkyl group, and R4 is a C1-C4 alkyl group; The substituent of pyridine is a C1-C3 alkoxy group.

9. The method for synthesizing a 1,3-diboron compound according to claim 8, characterized in that: Among them, The substituent of phenyl is C3-C4 alkyl, C1-C2 alkoxy, R1COOR2, fluorine, chlorine, bromine, benzene, furan, pyrazole, isoindoline-1,3-dione, 2,2-difluorobenzobisoxazole, 2-(6-methoxynaphthalen-2-yl)propionic acid, 3-benzoylphenyl)propionic acid, 5-(3,4,5-trimethoxyphenyl)-9-oxy-5,8,8a,9-tetrahydrofurano[3',4':6,7]naphtho[2,3-d][1,3] dioxacyclic-6(5aH)-one, 13-methyl-3-oxy-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthrene-17-one or 13-methyl-1-3-oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-17-yl valerate; R1 is C1-C2 alkyl, R2 is C1-C2 alkyl; The substituent of the indolyl group is R3COOR4, R3 is a C1-C2 alkyl group, and R4 is C3-C4; The substituent of pyridine is C1-C2 alkoxy.

10. The method for synthesizing a 1,3-diboron compound according to claim 9, characterized in that: The olefin compound is styrene, 4-tert-butylstyrene, 3,4-dimethoxystyrene, 3-methoxystyrene, 4-vinylphenyl acetate, 2-bromo-4,5-dimethoxystyrene, 4-fluorostyrene, 4-chlorostyrene, 4-phenylstyrene, 5-vinyl-1H-indole-1-carboxylic acid tert-butyl ester, 5-vinylbenzofuran, 1-(4-vinylphenyl)-1H-pyrazole, 2-(4-vinylbenzyl)isoindoline-1,3-dione, 2,2-difluoro-5-vinyl[ d [1,3]benzodioxazole, 2-methoxy-5-vinylpyridine, 2-vinylnaphthalene, 1,4-dihydro-1,4-epoxynaphthalene, 3-vinylthiophene, 2-(ethoxydimethylsilyl)ethylene, 2-(dimethylphenylsilyl)ethylene, 1-phenyl-1,3-butadiene, 4-vinylbenzyl 2-(6-methoxynaphthalen-2-yl)propionate, (5 R ,9 R )-5-(3,4,5-trimethoxyphenyl)-9-((4-vinylbenzyl)oxy)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3- d ][1,3]dioxetine-6(5aH)-one, (8 R ,9 S ,13 S ,14 S )-13-methyl-3-((4-vinylbenzyl)oxy)-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthrene-17-one, 4-vinylbenzyl 2-(3-benzoylphenyl)propionate or (8 R ,9 S ,13 S ,14 S )-13-methyl 1-3-((4-vinylbenzyl)oxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-17-yl pentanoate.

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