An organic boron reagent alpha-boryl oxime compound and a preparation method and application thereof

Abstract

The application discloses an organic boron reagent alpha-boryl oxime compound and a preparation method and application thereof, and belongs to the technical field of organic synthesis. N The alpha-boryl oxime compound is prepared by reacting a heterocyclic carbene borane adduct and a nitroso compound in an organic solvent. N The alpha-boryl oxime compound is prepared by simultaneously introducing an oxime group and a boron group functional group into both ends of the olefin with high selectivity through the boro-oximation reaction of the heterocyclic carbene borane, the nitrosamine compound and the olefin. The reaction avoids the use of a photosensitizer and a transition metal, has very good functional group tolerance and substrate universality, and also has good chemical selectivity, regioselectivity and stereoselectivity; the product alpha-boryl oxime compound can be efficiently used to synthesize various useful compounds through simple conversion, the types of the organic boron reagent are expanded, and the application prospect is good.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis technology, specifically relating to an organoboron reagent α-boronyl oxime compound, its preparation method, and its application. Background Technology

[0002] Organoboron compounds, due to their good stability and diverse reactivity (such as Suzuki cross-coupling and carbon-heteroatom bond formation reactions), have been widely used in agricultural chemistry, medicinal chemistry, and materials science (Suzuki, A. Angew. Chem. Int. Ed., 2011, 50, 6722; Xu, L.; Zhang, S.; Li, P. Chem. Soc. Rev., 2015, 44, 8848, etc.). Therefore, the development of CB bond formation reactions has long been a research focus in organic synthesis. Among known methods for synthesizing organoboron compounds, catalytic borylation reactions have significantly improved synthetic efficiency. Currently, various methods exist for catalytic CB bond formation reactions, including transition metal-catalyzed CB bond coupling reactions, selective CH bond borylation reactions, hydrogen borylation reactions of carbon-carbon multiple bonds, and carbene insertion into BH bonds. Among these, the boron functionalization reactions of alkenes and alkynes under transition metal-catalyzed CB bond construction systems are of particular importance because they can simultaneously introduce boron atoms and other important functional groups into organic molecules. Representative processes include diborylation, silylborylation, borostinization, cyanoborylation, alkyneborylation, and ammoniborylation. These reactions typically utilize boron reagents to form metal-boron reactive intermediates, followed by organometallic elementary reactions to obtain the target product.

[0003] In recent years, N Heterocyclic carbene (NHC) boranes have attracted increasing attention due to their superior air stability and ease of handling compared to traditional boron reagents. Notably, the low dissociation energy of the BH bond in NHC boranes promotes homolytic cleavage under thermal or photoredox conditions, resulting in the generation of boron radicals. Consequently, researchers have developed a series of carbon-carbon multi-bond radical borylation reactions based on NHC-boranes (Taniguchi, T). European Journal of Organic Chemistry , 2019, 2019 , 6308;Jin, J.; Xia, H.; Zhang, F.; Wang, Y. Chinese Journal of Organic Chemistry ., 2020, 40 ,2185; Chen, X.; Zhou, X.; He, J.; Liu, X. Synthesis , 2025, 57(e.g., 2539). Currently, there are only a few reports on NHC-borane-catalyzed boron functionalization of olefins / alkynes, and existing studies all involve activated internal alkenes and photoredox catalytic mechanisms (Shimoi, M.; Maeda, K.; Geib, SJ; Curran, DP; Taniguchi, T). Angewandte Chemie International Edition , 2019, 58 , 6357;Qi, J.; Zhang, F.-L.; Jin, J.-K.; Zhao, Q.; Li, B.; Liu, L.-X.; Wang, Y.-F. Angewandte Chemie International Edition , 2020, 59 , 12876;Zhu, C.; Yao, S.; Xie, J. Synthesis 2024 56 , 1711; Chen, Z.-L.; Ma,S.-C.; Tang, S.-Y.; Yu, H.-Y.; Zhao, Y.; Xuan, J. ACS Catalysis , 2025, 15 (7101). In such reactions, the redox potential of the photosensitizer not only needs to match the potentials of borane and other substrates, but also needs to effectively suppress the hydroboration reaction or olefin radical dimerization side reaction. These requirements largely limit the range of applicable olefin types and functional groups. Therefore, developing efficient and practical methods to achieve the reaction between olefins and... N The synthesis of organoboron reagents through the boron functionalization of heterocyclic carbene (NHC) boranes, thereby expanding their synthetic applications, is a technical problem that urgently needs to be solved in this field. Summary of the Invention

[0004] To address the shortcomings of the existing technologies, this invention provides an organoboron reagent α-boronyl oxime compound, its preparation method, and its application. Under room temperature conditions, it is prepared by blue light-induced... N - The boronization reaction of heterocyclic carbene boranes and nitrosamines with alkenes, while selectively introducing oxime and boron functional groups at both ends of the olefin, prepares an α-boron oxime compound. This reaction avoids the use of photosensitizers and transition metals, has very good functional group tolerance and substrate universality, and also has good chemoselectivity, regioselectivity and stereoselectivity.

[0005] One objective of this invention is to provide a method for preparing organoboron reagent α-boronyl oxime compounds, comprising the following steps: under room temperature blue light irradiation, using thiols R... 8 SH is a catalyst for olefins, N- A heterocyclic carbene borane adduct was reacted with a nitroso compound in an organic solvent for 30-48 h to obtain an α-boron oxime compound with the structural formula shown in formula (Ⅰ); Among them, R 2 It is H or alkyl; R 3 It is an alkyl or substituted aryl group; R 4 It is H, alkyl, or halogen; R 5 R 6 R 7 R 8 All are alkyl groups or alkyl groups substituted with functional groups.

[0006] Preferably, the olefin, N The molar ratio of the heterocyclic carbene borane adduct to the nitroso compound is 1:3:2.

[0007] Preferably, the molar ratio of the catalyst thiol to olefin is (0.2~0.5):1.

[0008] Preferably, the wavelength of the blue light irradiation is 437~471nm.

[0009] Preferably, the olefin has the structural formula shown in formula (II); N The structural formula of the heterocyclic carbene borane adduct is shown in formula (III); the structural formula of the nitroso compound is shown in formula (IV) or formula (V); the organic solvent is tetrahydrofuran, dioxane, ethyl acetate, benzene, toluene, trifluorotoluene, acetonitrile, benzonitrile, dichloromethane, 1,2-dichloroethane, N , N - any one or more of dimethylformamide, acetone, methanol, ethanol, and isopropanol; Among them, R 1 It is an aryl group with optional substitution, or an electron-withdrawing functional group; R 5 R 6 R 7 R 8 All are alkyl groups or alkyl groups substituted with functional groups.

[0010] Preferably, the optionally substituted aryl group is any one or more selected from phenyl, substituted phenyl, naphthyl, furan, thiophene, pyridyl, or indole; the other electron-withdrawing functional group is any one or more selected from ester, amide, cyano, or sulfonyl; and the alkyl group is C1-C6. 12 alkyl.

[0011] Preferably, the substituents in the substituted phenyl group are C1-C2. 12 Alkyl, C1~C 12Alkoxy, C1~C 12 Alkylthio group, C2~C 12 Acyloxy group, silicon group, hydroxyl group, cyano group, sulfonyl group, acetal, trifluoromethyl group, halogen, (C1~C) 12 alkyl)amino, di(C1~C 12 Alkyl)amino, C1~C 12 Acyl group, C2~C 12 Ester group, di(C1~C) 12 Any one or more of alkyl)amide groups; the number of substituents is 0 to 5.

[0012] Preferably, C1~C 12 The alkyl group is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, neohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, neoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, neooctyl, sec-octyl, or tert-octyl.

[0013] Preferably, C1~C 12 The acyl group is formyl, acetyl, propionyl, n-butyryl, isobutyryl, n-valeryl, isovaleryl, sec-valeryl, neovaleryl, n-hexanoyl, isohexanoyl, neohexanoyl, sec-hexanoyl, n-heptanoyl, isoheptanoyl, neoheptanoyl, sec-heptanoyl, n-octanoyl, isooctanoyl, neooctanoyl, sec-octanoyl, 1-cyclopropylformyl, 1-cyclobutylformyl, 1-cyclopentylformyl, 1-cyclohexylformyl, 1-cycloheptylformyl.

[0014] Preferably, C2~C 12 Acyloxy groups include acetyloxy, propionyloxy, n-butyryloxy, isobutyryloxy, n-valeryloxy, isovaleryloxy, sec-valeryloxy, neovaleryloxy, n-hexanoyloxy, isohexanoyloxy, neohexanoyloxy, sec-hexanoyloxy, n-heptanoyloxy, isoheptanoyloxy, neoheptanoyloxy, sec-heptanoyloxy, n-octanoyloxy, isooctanoyloxy, neooctanoyloxy, sec-octanoyloxy, 1-cyclopropylformyloxy, 1-cyclobutylformyloxy, 1-cyclopentylformyloxy, 1-cyclohexylformyloxy, and 1-cycloheptylformyloxy.

[0015] Preferably, C2~C 12 The ester group is methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, n-pentoxycarbonyl, isopentoxycarbonyl, neopentoxycarbonyl, secondary pentoxycarbonyl, tertiary pentoxycarbonyl, cyclopentoxycarbonyl, n-hexyloxycarbonyl, isohexyloxycarbonyl, neohexyloxycarbonyl, secondary hexyloxycarbonyl, tertiary hexyloxycarbonyl, cyclohexyloxycarbonyl, n-heptoxycarbonyl, isoheptoxycarbonyl, neoheptoxycarbonyl, secondary hexyloxycarbonyl, tertiary hexyloxycarbonyl, cycloheptoxycarbonyl.

[0016] A second objective of this invention is to provide an organoboron reagent α-boronyl oxime compound prepared by the above-described method.

[0017] Preferably, the organoboron reagent α-boronyl oxime compound includes the following compounds: .

[0018] A third objective of this invention is to provide the application of the above-mentioned organoboron reagents α-boronyl oxime compounds in the preparation of amino alcohol compounds.

[0019] Preferably, the application involves a catalytic Michael addition reaction of an organoboron reagent α-boronyl oxime compound with two equivalents of conjugated olefin ester to obtain an α-boronyl oxime ether compound with a single stereostructure. This α-boronyl oxime ether compound is then subjected to oxidation of the C-B bond and reduction of the C=N double bond to obtain an amino alcohol compound.

[0020] Compared with the prior art, the positive advantages of this invention are as follows: This invention, under room temperature blue light induction and thiol catalysis, through... N The boronization reaction of heterocyclic carbene boranes, nitrosamines, and alkenes, with the selective introduction of oxime and boron functional groups at both ends of the olefin, yields a novel organoboron reagent, α-boronyl oxime compounds. This reaction avoids the use of photosensitizers and transition metals, exhibits excellent functional group tolerance and substrate universality, and also demonstrates good chemoselectivity, regioselectivity, and stereoselectivity. Furthermore, this reaction can be applied to the late-stage modification of drug molecules. The resulting α-boronyl oxime compounds can be efficiently synthesized into various useful compounds through simple transformations. Moreover, the preparation method provided by this invention significantly expands the range of organoboron reagents and has excellent application prospects. Attached Figure Description

[0021] Figure 1 This is the 1H NMR spectrum of product 4aa prepared in Example 2 of this invention.

[0022] Figure 2 This is the 1H NMR spectrum of product 4ab prepared in Example 3 of this invention. Detailed Implementation

[0023] The following examples will help to further understand the present invention, but should not be construed as limiting the scope of the subject matter of the present invention to the following examples. All technologies implemented based on the above content of the present invention fall within the scope of the present invention. In the description of the present invention, unless otherwise specified, the methods used are conventional techniques in the art, the solvents used are purified and dried using standard procedures before use, and the reagents used are commercially available or synthesized according to existing literature methods and purified before use.

[0024] The following examples use compound abbreviations, the meanings of which are as follows: Me is methyl, Et is ethyl, i Pr is isopropyl. n Bu is n-butyl, Ph is phenyl. t Bu is tert-butyl, Bn is benzyl, Ts is p-toluenesulfonyl, and DMF is... N , N -Dimethylformamide, THF is tetrahydrofuran, PE is petroleum ether, EA is ethyl acetate, DCM is dichloromethane, NMR is nuclear magnetic resonance, and HRMS is high-resolution mass spectrometry.

[0025] Example 1 Blue light-induced boronization of olefins to prepare α-boron oxime compounds Weigh 0.5 mmol of the substrate olefin and 1.5 mmol of the substrate olefin into a glove box. N - A heterocyclic carbene borane, 1.0 mmol of a nitroso compound, was added to a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After being removed from the glove box, 0.2 mmol of a thiol catalyst was added. The reaction was carried out at room temperature under blue light irradiation for 40 h. After the reaction, the solvent was evaporated to dryness, and the target compound 4 was obtained by column chromatography. The chemical equation for the reaction is as follows: .

[0026] The reaction principles and chemical equations of Examples 2-28 are the same as those of Example 1, except that the specific reactants, reaction conditions and products in each example are different.

[0027] Example 2 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(4-(methoxycarbonyl)phenyl)ethyl)dihydroborate (4aa) includes the following steps: Weigh out 0.5 mmol of methyl 4-vinylbenzoate, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl) trihydroborate, and 1.0 mmol of [unclear - possibly a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(4-(methoxycarbonyl)phenyl)ethyl)dihydroborate (4aa) 0.132 g, the yield of the product is 88%, the melting point is 159~162 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4aa are as follows: 1 H NMR(600 MHz, DMSO-d6) δ 10.12 (s,1H), 7.88 (d, J = 8.4 Hz, 2H), 7.79 (d, J = 8.4 Hz, 2H), 7.16 (s, 2H), 3.84 (s, 3H), 3.53 (s, 6H), 1.92 (s, 2H), 1.78-1.23 (m, 2H). 13 C NMR (151 MHz, DMSO-d6)δ 166.23, 162.51, 143.05, 128.73, 128.33, 125.85, 120.65, 52.01, 35.11,16.31-15.38 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.19 (t, J = 88.1 Hz). HRMS (ESI)Calcd for [C 15 H 19 BN3O3, MH] + : 300.1514; Found: 300.1523.

[0028] Example 3 An organoboron reagent α-boronyl oxime compound ( E )-(2-(4-cyanophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 HThe preparation method of 3-imidazol-3-onthiol-2-yl)dihydroborate (4ab) includes the following steps: Weigh out 0.5 mmol of p-cyanostrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unspecified substance] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(2-(4-cyanophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H 0.111 g of 3-imidazol-3-onthiol-2-yl)dihydroborate (4ab) was obtained, with a yield of 83% and a melting point of 146–148 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ab are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.28 (s, 1H), 7.85 (d, J = 7.7 Hz, 2H), 7.75 (d, J = 7.7 Hz, 2H), 7.18 (s, 2H), 3.54 (s, 6H), 1.92 (s, 2H), 1.80-1.20 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 162.16, 142.97, 131.79,126.43, 120.71, 119.14, 109.82, 35.14, 16.3-15.4 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.2 (t, J = 87.4 Hz). HRMS (ESI) Calcd for [C 14 H 16 BN4O, MH] + : 267.1412;Found: 267.1422.

[0029] Example 4 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 HThe preparation method of 3-imidazol-3-onthiol-2-yl)[2-(4-(dimethylcarbamoyl)phenyl)-2-(hydroxyimino)ethyl]dihydroborate (4ac) includes the following steps: Weigh 0.5 mmol in the glove box. N , N 1.5 mmol (1,3-dimethyl-1H-imidazol-3-onthium-2-yl) trihydroborate, 1.0 mmol N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After being removed from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a colorless oily liquid product. E )-(1,3-dimethyl-1 H 0.125 g of 3-imidazol-3-onthiol-2-yl)[2-(4-(dimethylcarbamoyl)phenyl)-2-(hydroxyimino)ethyl] dihydroborate (4ac) was obtained, with a yield of 80%. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ac are as follows: 1 H NMR(600 MHz, DMSO-d6) δ 9.94(s, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.31 (d, J = 7.9 Hz, 2H), 7.16 (s, 2H), 3.55(s, 6H), 3.01-2.89 (m, 6H), 1.91 (s, 2H), 1.80-1.22 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 170.13, 162.66, 139.38, 135.24, 126.51, 125.41, 120.58, 54.89,52.94, 35.09, 16.63-15.89 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.16 (t, J = 87.6Hz). HRMS (ESI) Calcd for [C 16 H 22 BN4O2, MH] + : 313.1830; Found: 314.1840.

[0030] Example 5 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(4-(methanesulfonyl)phenyl)ethyl)dihydroborate (4ad) includes the following steps: Weigh out 0.5 mmol of 1-(methylsulfonyl)-4-vinylbenzene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H 0.146 g of 3-imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(4-(methanesulfonyl)phenyl)ethyl)dihydroborate (4ad) was obtained, with a yield of 91% and a melting point of 177–179 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ad are as follows: 1 H NMR (600 MHz, DMSO-d6) δ10.24 (s, 1H), 7.90 (d, J = 8.1 Hz, 2H), 7.84 (d, J = 8.2 Hz, 2H), 7.17 (s, 2H), 3.55 (s, 6H), 3.20 (s, 3H), 1.93 (s, 2H), 1.80-1.22 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 162.30, 143.41, 139.36, 126.59, 126.42, 120.72, 43.67, 35.18,16.48-15.62 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.22 (t, J = 88.9 Hz). HRMS (ESI)Calcd for [C 14 H19 BN3O3S, MH] + : 320.1235; Found: 320.1245.

[0031] Example 6 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H -imidazol-3-on-2- The preparation method of (2-(hydroxyimino)-2-(4-(trifluoromethyl)phenyl)ethyl)dihydroborate (4ae) includes the following steps: Weigh out 0.5 mmol of p-trifluoromethylstyrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk reaction tube, followed by the addition of 5 mL toluene. The tube was then sealed, removed from the glove box, and 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction was completed, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(4-(trifluoromethyl)phenyl)ethyl)dihydroborate (4ae) 0.101 g, the yield of the product is 65%, the melting point is 143~146 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ae are as follows: 1 H NMR (600 MHz, DMSO-d6) δ10.16 (s, 1H), 7.90 (d, J = 7.4 Hz, 2H), 7.65 (d, J = 8.1 Hz, 2H), 7.18 (s, 2H), 3.57 (s, 6H), 1.95 (s, 2H), 1.82-1.24 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ162.26, 142.45, 127.74 (q, 2 J C-F = 31.5 Hz), 126.33, 124.63 (q, 3 J C-F= 3.3 Hz), 124.50 (q, 1 J C-F = 270.3 Hz), 120.67, 35.13, 16.48-15.36 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.19 (t, J = 88.9 Hz). HRMS (ESI) Calcd for [C 14 H 16 BF3N3O, MH] + :310.1333; Found: 310.1345.

[0032] Example 7 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl)[2-(4-fluorophenyl)-2-(hydroxyimino)ethyl] dihydroborate (4af) includes the following steps: Weigh out 0.5 mmol of p-fluorostyrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl) trihydroborate, and 1.0 mmol of [unclear - possibly a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H 0.068 g of 3-imidazol-3-onthiol-2-yl)[2-(4-fluorophenyl)-2-(hydroxyimino)ethyl] dihydroborate (4af) was obtained, with a yield of 52% and a melting point of 127–130 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4af are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 9.85 (s, 1H), 7.78-7.70 (m, 2H), 7.20 (s, 2H), 7.13 (t, J = 8.7 Hz, 2H), 3.58 (s, 6H), 1.92 (s, 2H), 1.82-1.25 (m, 2H).13 C NMR (151 MHz, DMSO-d6) δ 162.22, 161.75 (d, 1 J C-F = 242.1Hz), 134.89 (d, 4 J C-F = 2.4 Hz), 127.60 (d, 3 J C-F = 7.7 Hz), 120.59, 114.42 (d, 2 J C-F =20.7 Hz), 35.09, 16.53-15.54 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.15 (t, J =88.2 Hz). HRMS (ESI) Calcd for [C 13 H 16 BFN3O, MH] + : 260.1365; Found: 260.1375.

[0033] Example 8 An organoboron reagent α-boronyl oxime compound ( E )-(2-(4-chlorophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl) dihydroborate (4 ag) includes the following steps: Weigh out 0.5 mmol of p-chlorostyrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N - Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of benzonitrile was added to the tube, which was then sealed. After being removed from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product, an α-boronyl oxime compound. E )-(2-(4-chlorophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H0.072 g of 3-imidazol-3-onthiol-2-yl)dihydroborate (4 ag) was obtained, with a yield of 52% and a melting point of 128–130 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product (4 ag) are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 9.92 (s,1H), 7.69 (d, J = 7.7 Hz, 2H), 7.33 (d, J = 7.8 Hz, 2H), 7.16 (s, 2H), 3.54 (s, 6H), 1.89 (s, 2H), 1.81-1.18 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 162.65,137.71, 132.50, 128.17, 127.88, 121.06, 35.56, 16.89-15.88 (m). 11 B NMR (193MHz, DMSO-d6) δ -28.15 (t, J = 87.4 Hz). HRMS (ESI) Calcd for [C 13 H 16 BClN3O, MH] + : 276.1069; Found: 276.1079.

[0034] Example 9 An organoboron reagent, an α-boronyl oxime compound (E)-(2-(4-bromophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl)dihydroborate (4ah) includes the following steps: Weigh out 0.5 mmol of p-bromostyrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product (E)-(2-(4-bromophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H0.118 g of 3-imidazol-3-onthiol-2-yl)dihydroborate (4ah) was obtained, with a yield of 74% and a melting point of 147–149 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ah are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 9.92 (s, 1H), 7.63 (d, J = 8.5 Hz, 2H), 7.47 (d, J = 8.5 Hz, 2H), 7.16 (s, 2H), 3.54 (s, 6H), 1.88 (s, 2H), 1.78-1.23 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 162.29, 137.68, 130.68,127.82, 120.75, 120.65, 35.16, 16.32-15.40 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.17 (t, J = 88.5 Hz). HRMS (ESI) Calcd for [C 13 H 16 BBrN3O, MH] + : 320.0564;Found: 320.0573.

[0035] Example 10 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(4-(p-toluenesulfonyloxy)phenyl)ethyl)dihydroborate (4ai) includes the following steps: Weigh out 0.5 mmol of 4-vinylphenyl-4-methylbenzenesulfonate, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or ingredient] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the solid was separated by column chromatography to obtain a white solid. E)-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(4-(p-toluenesulfonyloxy)phenyl)ethyl)dihydroborate (4ai) 0.130 g, the yield of the product was 63%, and the melting point was 149~152ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ai are as follows: 1 H NMR (600 MHz, DMSO-d6)δ 9.95 (s, 1H), 7.73 (d, J = 8.0 Hz, 2H), 7.63 (d, J = 8.5 Hz, 2H), 7.46 (d, J =8.0 Hz, 2H), 7.14 (s, 2H), 6.94 (d, J = 8.5 Hz, 2H), 3.51 (s, 6H), 2.41 (s, 3H), 1.86 (s, 2H), 1.73-1.19 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 162.13,148.40, 145.77, 137.53, 131.54, 130.20, 128.23, 127.13, 121.29, 120.62,35.09, 21.19, 16.34-15.35 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.21 (t, J = 84.5Hz). HRMS (ESI) Calcd for [C 20 H 23 BN3O4S, MH] + : 412.1497; Found: 412.1502.

[0036] Example 11 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)[2-(hydroxyimino)-2-(4-((4-methyl- N The preparation method of [-toluenesulfonylphenyl)sulfonylamino)phenyl)ethyl] dihydroborate (4aj) includes the following steps: Weigh 0.5 mmol of 4-methyl- in the glove box. N-p-Toluenesulfonyl- N 1.5 mmol of (4-vinylphenyl)benzenesulfonamide, 1.0 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, 1.0 mmol N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)[2-(hydroxyimino)-2-(4-((4-methyl- N [-Toluenesulfonylphenyl)sulfonylamino)phenyl)ethyl] dihydroborate (4aj) 0.160 g, the yield of this product is 57%, and the melting point is 157~159 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4aj are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.11 (s, 1H), 7.73-7.66(t, J = 9.9 Hz, 6H), 7.48 (d, J = 8.1 Hz, 4H), 7.17 (s, 2H), 6.94 (d, J = 8.2 Hz, 2H), 3.55 (s, 6H), 2.44 (s, 6H), 1.92 (s, 2H), 1.81-1.25 (m, 2H). 13 C NMR (151MHz, DMSO-d6) δ 162.32, 145.34, 140.27, 135.83, 132.52, 130.58, 129.89,128.02, 126.53, 120.60, 35.07, 21.15, 16.12-15.33 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.18 (t, J = 87.9 Hz). HRMS (ESI) Calcd for [C 27 H 30 BN4O5S2, MH] + :565.1745; Found: 565.1753.

[0037] Example 12 An organoboron reagent α-boronyl oxime compound ( E )-(2-([1,1'-biphenyl]-4-yl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl)dihydroborate (4ak) includes the following steps: Weigh out 0.5 mmol of p-phenylstyrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of... in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of benzonitrile was added to the tube, which was then sealed. After being removed from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(2-([1,1'-biphenyl]-4-yl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H 0.081 g of 3-imidazol-3-onthiol-2-yl)dihydroborate (4ak) was obtained, with a yield of 51% and a melting point of 155–157 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ak are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 9.87 (s, 1H),7.80 (d, J = 8.2 Hz, 2H), 7.68 (d, J = 7.7 Hz, 2H), 7.61 (d, J = 8.2 Hz, 2H), 7.46(t, J = 7.6 Hz, 2H), 7.35 (t, J = 7.4 Hz, 1H), 7.17 (s, 2H), 3.58 (s, 6H), 1.96 (s, 2H), 1.86-1.27 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 162.87, 139.96,139.04, 137.66, 128.96, 127.36, 126.49, 126.35, 126.01, 120.62, 35.19, 16.58-15.56 (m). 11B NMR (193 MHz, DMSO-d6) δ -28.06 (t, J = 84.2 Hz). HRMS (ESI) Calcdfor [C 19 H 21 BN3O, MH] + : 318.1772; Found: 318.1781.

[0038] Example 13 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-phenylethyl) dihydroborate (4al) includes the following steps: Weigh out 0.5 mmol of styrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl) trihydroborate, and 1.0 mmol of... in a glove box. N - Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of benzonitrile was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain 0.050 g of a white solid product (4al). The yield of this product was 41%, and the melting point was 139–141 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4al are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 9.78 (s, 1H), 7.68 (d, J =7.6 Hz, 2H), 7.28 (t, J = 7.3 Hz, 2H), 7.23 (t, J = 7.2 Hz, 1H), 7.15 (s, 2H), 3.54 (s, 6H), 1.91 (s, 2H), 1.80-1.25 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ163.62, 138.96, 128.13, 127.85, 126.20, 121.00, 35.54, 17.07-15.86 (m). 11B NMR(193 MHz, DMSO-d6) δ -28.09 (t, J = 88.5 Hz). HRMS (ESI) Calcd for [C 13 H 17 BN3O,MH] + : 242.1459; Found: 242.1467.

[0039] Example 14 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(3-(methoxycarbonyl)phenyl)ethyl)dihydroborate (4am) includes the following steps: Weigh out 0.5 mmol of methyl 3-vinylbenzoate, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - possibly a specific compound or ingredient] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(3-(methoxycarbonyl)phenyl)ethyl)dihydroborate (4am) 0.115 g, the yield of the product was 76%, and the melting point was 137~140 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4am are as follows: 1 H NMR (600 MHz, DMSO-d6) δ10.01 (s, 1H), 8.28 (s, 1H), 7.94 (d, J = 7.6 Hz, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.44 (t, J = 7.7 Hz, 1H), 7.15 (s, 2H), 3.86 (s, 3H), 3.54 (s, 6H), 1.92 (s, 2H), 1.80-1.21 (m, 2H). 13C NMR (151 MHz, DMSO-d6) δ 166.43, 162.20, 138.79,130.32, 129.22, 128.26, 128.11, 126.44, 120.68, 52.14, 35.11, 16.31-15.32(m). 11 B NMR (193 MHz, DMSO-d6) δ -28.23 (t, J = 90.0 Hz). HRMS (ESI) Calcd for[C 15 H 19 BN3O3, MH] + : 300.1514; Found: 300.1524.

[0040] Example 15 An organoboron reagent α-boronyl oxime compound ( E )-(2-(3-cyanophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl) dihydroborate (4an) includes the following steps: Weigh out 0.5 mmol of 3-vinylbenzonitrile, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(2-(3-cyanophenyl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H 0.094 g of 3-imidazol-3-onthiol-2-yl)dihydroborate (4an) was obtained, with a yield of 70% and a melting point of 126–128 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4an are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.16 (s, 1H), 8.02-7.96 (m, 2H), 7.71 (d, J = 7.6 Hz, 1H), 7.51 (t, J= 7.8 Hz, 1H), 7.18 (s,2H), 3.54 (s, 6H), 1.91 (s, 2H), 1.78-1.20 (m, 2H). 13 C NMR (151 MHz, DMSO-d6)δ 161.58, 139.52, 130.96, 130.28, 129.12, 129.02, 120.68, 119.01, 110.96,35.09, 16.18-15.20 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.21 (t, J = 88.0 Hz).HRMS (ESI) Calcd for [C 14 H 16 BN4O, MH] + : 267.1412; Found: 267.1422.

[0041] Example 16 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(3-(methanesulfonyl)phenyl)ethyl)dihydroborate (4ao) includes the following steps: Weigh out 0.5 mmol of 1-(methylsulfonyl)-3-vinylbenzene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -Imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(3-(methanesulfonyl)phenyl)ethyl)dihydroborate (4ao) 0.144 g, the yield of the product is 90%, the melting point is 149~151 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ao are as follows: 1H NMR (600 MHz, DMSO-d6)δ 10.16 (s, 1H), 8.20 (s, 1H), 8.01 (d, J = 7.9 Hz, 1H), 7.82 (d, J = 7.8 Hz, 1H), 7.58 (t, J = 7.9 Hz, 1H), 7.16 (s, 2H), 3.55 (s, 6H), 3.20 (s, 3H), 1.94(s, 2H), 1.81-1.24 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 161.86, 140.52,139.49, 130.51, 129.03, 125.81, 123.78, 120.68, 43.65, 35.10, 16.38-15.36(m). 11 B NMR (193 MHz, DMSO-d6) δ -28.19 (t, J = 84.5 Hz). HRMS (ESI) Calcd for[C 14 H 19 BN3O3S, MH] + : 320.1235; Found: 320.1245.

[0042] Example 17 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl)[2-(2-fluorophenyl)-2-(hydroxyimino)ethyl] dihydroborate (4ap) includes the following step: Weigh out 0.5 mmol of 2-fluorostyrene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - possibly a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After being removed from the glove box, 0.5 mmol of tert-butylthiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H0.066 g of 3-imidazol-3-onthiol-2-yl)[2-(2-fluorophenyl)-2-(hydroxyimino)ethyl] dihydroborate (4ap) was obtained, with a yield of 51% and a melting point of 139–142 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ap are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 9.95 (s, 1H), 7.39 (t, J = 7.6 Hz, 1H), 7.27 (q, J = 7.2 Hz, 1H), 7.16 (s, 2H), 7.14-7.06 (m, 2H), 3.57(s, 6H), 1.93 (s, 2H), 1.69-1.12 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 162.01,159.60 (d, 1 J C-F = 123.8 Hz), 130.22 (d, 5 J C-F = 4.1 Hz), 128.93 (d, 4 J C-F = 8.5 Hz), 127.52 (d, 3 J C-F = 12.5 Hz), 123.65 (d, 6 J C-F = 3.0 Hz), 120.62, 115.57 (d, 2 J C-F =22.8 Hz), 35.06, 18.66-17.65 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.70 (t, J =88.8 Hz). HRMS (ESI) Calcd for [C 13 H 16 BFN3O, MH] + : 260.1365; Found: 260.1375.

[0043] Example 18 An organoboron reagent α-boronyl oxime compound ( E)-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(2-(methanesulfonyl)phenyl)ethyl)dihydroborate (4aq) includes the following steps: Weigh out 0.5 mmol of 1-(methylsulfonyl)-2-vinylbenzene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(2-(methanesulfonyl)phenyl)ethyl)dihydroborate (4aq) 0.091 g, the yield of the product was 57%, and the melting point was 156~159ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4aq are as follows: 1 H NMR(600 MHz, DMSO-d6)δ 9.90 (s, 1H), 7.94 (d, J = 7.7 Hz, 1H), 7.78 (d, J = 7.3 Hz, 1H), 7.70 (t, J =7.1 Hz, 1H), 7.55 (t, J = 7.3 Hz, 1H), 7.24 (s, 2H), 3.68 (s, 6H), 1.88-1.29(m, 4H). 13 C NMR (151 MHz, DMSO-d6) δ 165.03, 140.71, 138.59, 132.71, 130.80,128.57, 127.74, 120.74, 45.49, 35.18, 22.05-20.91 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.53 (t, J = 88.0 Hz). HRMS (ESI) Calcd for [C 14 H 19BN3O3S, MH] + :320.1235; Found: 320.1245.

[0044] Example 19 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(naphth-2-yl)ethyl)dihydroborate (4ar) includes the following steps The preparation method of (4ar)-2-(naphthyl-2-yl)ethyl)dihydroborate includes the following steps: Weigh out 0.5 mmol of 2-vinylnaphthalene, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(naphth-2-yl)ethyl)dihydroborate (4ar) 0.117 g, the yield of the product is 80%, the melting point is 172~174 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ar are as follows: 1 H NMR(600 MHz, DMSO-d6) δ 9.94 (s, 1H), 8.12 (s,1H), 7.93 (d, J = 8.6 Hz, 1H), 7.90 (d, J = 7.3 Hz, 1H), 7.84 (d, J = 7.5 Hz, 1H), 7.78 (d, J = 8.7 Hz, 1H), 7.47 (p, J = 6.7 Hz, 2H), 7.14 (s, 2H), 3.55 (s, 6H), 2.05 (s, 2H), 1.89-1.34 (m, 2H). 13C NMR (151 MHz, DMSO-d6) δ 163.01, 135.81,132.95, 132.62, 128.29, 127.34, 126.86, 125.94, 125.79, 124.93, 123.98,120.61, 35.15, 16.21-15.35 (m). 11 B NMR (193 MHz, DMSO-d6) δ -27.98 (t, J = 84.9Hz). HRMS (ESI) Calcd for [C 17 H 19 BN3O, MH] + : 292.1616; Found: 292.1626.

[0045] Example 20 An organoboron reagent α-boronyl oxime compound ( E )-(2-(5-(4-chlorophenyl)furan-2-yl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl)dihydroborate (4as) includes the following steps: Weigh out 0.5 mmol of 2-(4-chlorophenyl)-5-vinylfuran, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(2-(5-(4-chlorophenyl)furan-2-yl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H 0.108 g of 3-imidazol-3-onthiol-2-yl)dihydroborate (4as) was obtained, with a yield of 63% and a melting point of 163–166 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4as are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 9.99 (s, 1H), 7.66 (d, J = 8.5 Hz, 2H), 7.47 (d,J = 8.5 Hz, 2H), 7.15(s, 2H), 6.95 (d, J = 3.4 Hz, 1H), 6.57 (d, J = 3.4 Hz, 1H), 3.58 (s, 6H), 1.83 (s, 2H), 1.77-1.22 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 156.53, 152.61,150.69, 131.54, 129.18, 128.93, 124.85, 120.60, 109.59, 107.93, 35.06, 16.02-15.42 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.07 (t, J = 88.8 Hz). HRMS (ESI) Calcdfor [C 17 H 18 BClN3O2, MH] + : 342.1175; Found: 342.1184.

[0046] Example 21 An organoboron reagent α-boronyl oxime compound ( E )-(2-(6-bromopyridin-2-yl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl) dihydroborate (4at) includes the following steps: Weigh out 0.5 mmol of 2-bromo-6-vinylpyridine, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl) trihydroborate, and 1.0 mmol of [unclear - possibly a specific compound or product] in a glove box. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(2-(6-bromopyridin-2-yl)-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H0.131 g of 3-imidazolium-3-onthiol-2-yl)dihydroborate (4at) was obtained, with a yield of 81% and a melting point of 162–164 °C. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4at are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.39(s, 1H), 7.68 (d, J = 7.7 Hz, 1H), 7.57 (t, J = 7.7 Hz, 1H), 7.39 (d, J = 7.7 Hz,1H), 7.05 (s, 2H), 3.56 (s, 6H), 2.03 (s, 2H), 1.71-1.09 (m, 2H). 13 C NMR (151MHz, DMSO-d6) δ 164.15, 157.50, 140.00, 138.86, 126.35, 120.45, 118.88,35.04, 14.91-13.72 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.49 (t, J = 87.3 Hz).HRMS (ESI) Calcd for [C 12 H 15 BBrN4O, MH] + : 321.0517; Found: 321.0525.

[0047] Example 22 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(3-ethoxy-2-(hydroxyimino)-3-oxopropyl) dihydroborate (4ba) includes the following steps: Weigh out 0.5 mmol of ethyl acrylate, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl) trihydroborate, and 1.0 mmol of... in a glove box. N-Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After being removed from the glove box, 0.5 mmol of tert-butylthiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(3-ethoxy-2-(hydroxyimino)-3-oxopropyl)dihydroborate (4ba) 0.076 g, the yield of the product was 64%, and the melting point was 144~146 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ba are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.60 (s, 1H), 7.24(s, 2H), 4.03 (q, J = 7.1 Hz, 2H), 3.62 (s, 6H), 1.71 (s, 2H), 1.65-1.12 (m,5H). 13 C NMR (151 MHz, DMSO-d6) δ 165.32, 159.19, 120.81, 59.89, 35.12, 15.75-14.78 (m), 14.12. 11 B NMR (193 MHz, DMSO-d6) δ -28.85 (t, J = 89.4 Hz). HRMS(ESI) Calcd for [C 10 H 17 BN3O3, MH] + Found: 238.1357 Found: 238.1365.

[0048] Example 23 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthi-2-yl)(2-(hydroxyimino)-3-oxo-3-(phenylamino)propyl) dihydroborate (4bb), including Includes the following steps: Weigh 0.5 mmol in the glove box. N 1.5 mmol of phenylacrylamide (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, 1.0 mmolN - Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After being removed from the glove box, 0.5 mmol of tert-butylthiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a colorless oily liquid product. E )-(1,3-dimethyl-1 H -imidazol-3-onthi-2-yl)(2-(hydroxyimino)-3-oxo-3-(phenylamino)propyl)dihydroborate (4bb) 0.080 g, the yield of this product is 56%, and the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4bb are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.43 (s, 1H), 9.41 (s, 1H), 7.69 (d, J = 8.2 Hz, 2H), 7.32 (t, J = 7.7 Hz, 2H), 7.26 (s, 2H), 7.07(t, J = 7.3 Hz, 1H), 3.70 (s, 6H), 1.84 (s, 2H), 1.75-1.13 (m, 2H). 13 C NMR (151MHz, DMSO-d6) δ 163.45, 162.13, 138.86, 128.53, 123.06, 120.77, 119.79,35.19, 14.36-13.50 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.75 (t, J = 90.1 Hz).HRMS (ESI) Calcd for [C 14 H 18 BN4O2, MH] + : 285.1517; Found: 285.1527.

[0049] Example 24 An organoboron reagent α-boronyl oxime compound (2-cyano-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-onthiol-2-yl)dihydroborate (4bc) includes the following steps: Weigh out 0.5 mmol of acrylonitrile, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of... in a glove box. N - Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.5 mmol of tert-butylthiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a colorless oily liquid product (2-cyano-2-(hydroxyimino)ethyl)(1,3-dimethyl-1 H 0.084 g of 3-imidazol-3-onthiol-2-yl)dihydroborate (4bc) was obtained, with a yield of 87%. The mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4bc are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 11.60 (s, 1H), 11.54 (s, 0.34H), 7.31 (s, 2H), 7.29 (s, 0.68H), 3.67 (s, 2.17H), 3.65 (s, 6H), 1.78-1.24 (m, 6H). 13 C NMR (151MHz, DMSO-d6) δ 146.16, 144.48, 139.22, 121.70, 121.59, 117.85, 117.59,112.93, 36.28, 35.65, 22.70-21.64 (m). 11 B NMR (193 MHz, DMSO-d6) δ -27.21~-29.93 (m). HRMS (ESI) Calcd for [C8H 12 BN4O, MH] + : 191.1099; Found: 191.1102.

[0050] Example 25 An organoboron reagent α-boronyl oxime compound ( E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(benzenesulfonyl)ethyl)dihydroborate (4bd) includes the following steps: Weigh out 0.5 mmol of phenylvinyl sulfone, 1.5 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, and 1.0 mmol of [unclear - likely a specific compound or product] in a glove box. N - Nitromorpholine was placed in a 10 mL Schlenk tube. 5 mL of toluene was added to the tube, which was then sealed. After being removed from the glove box, 0.5 mmol of tert-butylthiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a colorless oily liquid product. E )-(1,3-dimethyl-1 H -imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(benzenesulfonyl)ethyl)dihydroborate (4bd) 0.092 g, the yield of this product is 60%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4bd are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 11.13 (s, 1H), 7.78 (d, J =7.9 Hz, 2H), 7.68 (t, J = 7.4 Hz, 1H), 7.60 (t, J = 7.7 Hz, 2H), 7.24 (s, 2H), 3.60 (s, 6H), 1.82 (s, 2H), 1.74-1.21 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ169.10, 140.32, 133.77, 129.44, 128.78, 121.34, 35.54, 15.74-14.68 (m). 11 B NMR(193 MHz, DMSO-d6) δ -28.59 (t, J = 91.8 Hz). HRMS (ESI) Calcd for [C 13 H 17 BN3O3S,MH] + : 306.1078; Found: 306.1087.

[0051] Example 26 An organoboron reagent α-boronyl oxime compound (1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(( E )-2-(hydroxyimino)-2-(4-((((5) R ,5aR ,8a R 9 R )-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofurano[3',4':6,7]naphtho[2,3- d The preparation method of [1,3]dioxacyclopentan-5-yl)oxy)carbonyl)phenyl)ethyl)dihydroborate (4ca) includes the following steps: Weigh 0.4 mmol (5) into the glove box. R ,5a R ,8a R 9 R )-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofurano[3',4':6,7]naphtho[2,3- d [1,3]dioxolane-5-yl-4-vinylbenzoate, 1.2 mmol (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate, 0.8 mmol N -Nitromorpholine was placed in a 10 mL Schlenk tube. 4 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a white solid product (1,3-dimethyl-1-nitrosomorpholine). H -imidazol-3-onthiol-2-yl)(( E )-2-(hydroxyimino)-2-(4-((((5) R ,5a R ,8a R 9 R )-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofurano[3',4':6,7]naphtho[2,3- d [1,3]dioxanepent-5-yl)oxy)carbonyl)phenyl)ethyl)dihydroborate (4ca) 0.161 g, the yield of this product is 59%, and the melting point is 141~144 ºC; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4ca are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.13 (s, 1H),7.94 (d, J = 7.7 Hz, 2H), 7.85 (d, J= 7.7 Hz, 2H), 7.19 (s, 2H), 7.02 (s, 1H), 6.66 (s, 1H), 6.43 (s, 2H), 6.15 (d, J = 9.0 Hz, 1H), 6.04 (s, 2H), 4.62 (d, J =3.0 Hz, 1H), 4.45 (t, J = 6.6 Hz, 1H), 4.31 (t, J = 9.1 Hz, 1H), 3.69 (s, 6H), 3.63 (s, 3H), 3.56 (s, 6H), 2.91 (p, J = 9.5 Hz, 1H), 1.94 (s, 2H), 1.77-1.24(m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 174.40, 166.52, 162.97, 152.58, 147.92,147.49, 143.83, 136.89, 136.08, 133.00, 129.44, 129.29, 128.71, 126.41,121.11, 109.82, 108.49, 107.57, 101.92, 73.95, 71.37, 60.38, 56.16, 44.72,43.40, 38.95, 35.59, 16.90-15.94 (m). 11 B NMR (193 MHz, DMSO-d6) δ -28.29 (t, J =110.7 Hz). HRMS (ESI) Calcd for [C 36 H 37 BN3O 10 , MH] + : 682.2567; Found: 682.2574.

[0052] Example 27 An organoboron reagent α-boronyl oxime compound ( R , E )-(1,3-dimethyl-1 H The preparation method of 3-imidazol-3-on-2-yl)(2-(hydroxyimino)-2-(4-(methyl(3-phenyl-3-(o-tolyloxy)propyl)carbamoyl)phenyl)ethyl)dihydroborate (4cb) includes the following steps: Weigh 0.4 mmol (in the glove box) R )- N -methyl- N 1.2 mmol of 3-(3-phenyl-3-(o-tolyloxy)propyl)-4-vinylbenzamide, and 0.8 mmol of (1,3-dimethyl-1H-imidazol-3-onthium-2-yl)trihydroborate. N -Nitromorpholine was placed in a 10 mL Schlenk tube. 4 mL of toluene was added to the tube, which was then sealed. After being removed from the glove box, 0.2 mmol of ethylenedithiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the product was separated by column chromatography to obtain a colorless oily liquid product. R , E )-(1,3-dimethyl-1 H -imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(4-(methyl(3-phenyl-3-(o-tolyloxy)propyl)carbamoyl)phenyl)ethyl)dihydroborate (4cb) 0.183 g, the yield of this product is 87%; the mass spectrometry and nuclear magnetic resonance spectra of the obtained product 4cb are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.08-9.86 (m, 1H),7.79-7.66 (m, 2H), 7.52-6.88 (m, 11H), 6.81-6.54 (m, 2H), 5.33 (d, J = 141.9Hz, 1H), 3.76-3.46 (m, 8H), 3.05-2.84 (m, 3H), 2.37-2.04 (m, 4H), 1.96 (s,3H), 1.83-1.34 (m, 2H). 13 C NMR (151 MHz, DMSO-d6) δ 171.15, 170.54, 163.08,155.87, 155.48, 142.14, 141.70, 139.75, 135.88, 130.84, 128.93, 127.92,126.88, 126.71, 126.28, 126.13, 125.90, 120.98, 120.50, 113.17, 112.76,77.09, 75.93, 47.98, 44.51, 37.71, 37.11, 36.05, 35.54, 32.66, 16.64, 16.42.11 B NMR (193 MHz, DMSO-d6) δ -27.98 (t, J = 84.9 Hz). HRMS (ESI) Calcd for[C 31 H 36 BN4O3, MH] + : 523.2875; Found: 523.2881.

[0053] Example 28 An organoboron reagent α-boronyl oxime compound ( E )-3-(((2 R 8 S 9 S 10 R ,13 R ,14 S 17 R )-10,13-dimethyl-17-(( R )-6-methylheptane-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecano-1 H -cyclopentane[ a The preparation method of phenanthrene-2-yl)oxy)-2-(hydroxyimino)-3-oxopropyl)(1,3-dimethyl-1H-imidazol-3-onthium-2-yl)dihydroborate (4cc) includes the following steps: Weigh 0.4 mmol (2) into the glove box. R 8 S 9 S 10 R ,13 R ,14 S 17 R )-10,13-dimethyl-17-[( R )-6-methylheptane-2-yl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecano-1 H -cyclopentane[ a 1.2 mmol of phenanthrene-2-yl acrylate (1,3-dimethyl-1H-imidazol-3-onthium-2-yl) trihydroborate, 0.8 mmol N-Nitromorpholine was placed in a 10 mL Schlenk tube. 4 mL of toluene was added to the tube, which was then sealed. After removing the tube from the glove box, 0.5 mmol of tert-butylthiol catalyst was added. The reaction was carried out at room temperature for 40 h under blue light irradiation at a wavelength of 437–471 nm. After the reaction, the solvent was evaporated to dryness, and the solid was separated by column chromatography to obtain a white solid. E )-3-(((2 R 8 S 9 S 10 R ,13 R ,14 S 17 R )-10,13-dimethyl-17-(( R )-6-methylheptane-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecano-1 H -cyclopentane[ a 0.130 g of phenanthrene-2-yl)oxy)-2-(hydroxyimino)-3-oxopropyl)(1,3-dimethyl-1H-imidazol-3-onthium-2-yl)dihydroborate (4 cc) was obtained, with a yield of 56% and a melting point of 177–179 °C. The mass spectrometry and nuclear magnetic resonance spectra of the 4 cc product are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.54 (s, 1H), 7.20 (s, 2H), 5.33 (s, 1H), 4.43 (s, 1H), 3.60 (s, 6H), 2.22 (s, 2H), 2.01-1.86 (m, 2H), 1.85-1.64 (m, 5H), 1.56-1.44 (m, 5H), 1.43-1.28 (m, 6H), 1.26-1.18 (m, 2H), 1.16-1.01 (m, 7H), 0.99-0.86 (m, 9H), 0.83 (d, J = 6.1 Hz, 6H), 0.64 (s, 3H). 13C NMR (151 MHz, DMSO-d6) δ 164.92,159.59, 139.85, 122.86, 122.43, 121.12, 73.49, 56.59, 56.14, 49.94, 42.28,39.47, 38.09, 37.00, 36.50, 36.20, 36.05, 35.78, 35.48, 31.79, 28.26, 27.87,27.76, 27.48, 24.30, 23.87, 23.00, 22.77, 21.02, 19.33, 18.93, 16.11-15.34 (m), 12.04. 11 B NMR (193 MHz, DMSO-d6) δ -28.99 (t, J = 80.9 Hz). HRMS (ESI)Calcd for [C 35 H 57 BN3O3, MH] + : 578.4487; Found: 578.4494.

[0054] Example 29 α-boronyl oxime compounds ( E )-(1,3-dimethyl-1 H The application of 4aa (-imidazol-3-onthiol-2-yl)(2-(hydroxyimino)-2-(4-(methoxycarbonyl)phenyl)ethyl)dihydroborate in the preparation of amino alcohol compounds, and the specific process of synthesizing amino alcohols from 4aa are as follows: (1) 301 mg 4aa (1.0 mmol), 200 mg 1ba (2.0 mmol), and 78.6 mg Ph3P (0.3 mmol) were added sequentially to a dry 25 mL Schlenk tube. Then, 5 mL of acetonitrile was added under a nitrogen atmosphere, and the reaction was carried out at 65 °C for 48 h. After the reaction, the system was diluted with ethyl acetate (EA), and column chromatography was performed (petroleum ether:ethyl acetate (v / v) = 2:1~1:3 as eluent) to obtain 0.382 g of white solid compound 6 (0.95 mmol). The yield of compound 6 was 95%, and its melting point was 88~90 °C. The mass spectrometry and nuclear magnetic resonance spectra of compound 6 are as follows: 1 H NMR (600 MHz, DMSO-d6) δ 7.91 (d, J = 8.0 Hz, 2H), 7.81 (d, J= 8.0 Hz,2H), 7.22 (s, 2H), 4.07 (q, J = 7.1 Hz, 2H), 3.98 (t, J = 6.2 Hz, 2H), 3.85 (s,3H), 3.54 (s, 6H), 2.47 (t, J = 6.2 Hz, 2H), 1.90 (s, 2H), 1.78-1.23 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H). 13 C NMR (151 MHz, DMSO-d6) δ 171.45, 166.52, 164.67,142.20, 129.39, 129.21, 126.58, 121.12, 69.00, 60.28, 52.46, 35.49, 34.73,18.25-17.26 (m), 14.49. 11 B NMR (193 MHz, DMSO-d6) δ -28.10 (t, J = 86.9 Hz).HRMS (ESI) Calcd for [C 20 H 28 BN3NaO5, M+Na] + Found: 424.2014; Found: 424.2011. The reaction equation is as follows: (2) Add 120 mg of compound 6 (0.3 mmol) obtained in step (1) to a 25 mL Schlenk tube, then add acetonitrile / methanol (1.5 mL / 1.5 mL) in a volume ratio of 1:1. Slowly add 0.34 mL of 30% H2O2 solution (10.0 equiv) to the system at 35 °C. After the addition is complete, continue the reaction at this temperature for 1 h. After the reaction is complete, extract with EA (10 mL*3). After drying the organic phase with anhydrous sodium sulfate, separate by column chromatography (using petroleum ether:ethyl acetate (v / v) = 5:1~1:1 as the eluent) to obtain 0.051 g of colorless oily liquid compound 7 (0.165 mmol). The yield of compound 7 is 55%. The detection data of the mass spectrum and nuclear magnetic resonance spectrum of compound 7 are as follows: 1 H NMR (600MHz, CDCl3) δ 7.98-7.92 (m, 2H), 7.64 (d, J= 8.1 Hz, 1.7H), 7.47 (d, J = 8.0 Hz,0.32H), 4.57 (s, 1.67H), 4.44-4.39 (m, 2H), 4.30 (t, J = 6.3 Hz, 0.35H), 4.11-4.01 (m, 2H), 3.83 (s, 3H), 3.09 (br, 1H), 2.66 (t, J = 6.0 Hz, 1.68H), 2.59(t, J = 6.3 Hz, 0.33H), 1.19-1.12 (m, 3H). 13 C NMR (151 MHz, CDCl3) δ 171.65,171.38, 166.67, 166.47, 158.17, 154.48, 138.35, 135.59, 130.80, 129.72,129.46, 128.21, 126.76, 70.12, 70.06, 63.71, 60.88, 60.69, 59.95, 52.30,52.26, 34.66, 34.61, 14.19. HRMS (ESI) Calcd for [C 15 H 19 [NNaO6, M+Na] + :322.1105; Found:322.1111. (3) Add 83 mg of compound 7 (0.27 mmol) obtained in step (2) to a 25 mL Schlenk tube, then add 2.7 mL of solvent acetic acid, followed by two batches of sodium cyanoborohydride (34 mg, 0.54 mmol in total). React at room temperature for 12 h. After the reaction, dilute the system with EA and separate by column chromatography (using petroleum ether: ethyl acetate (v / v) = 3:1~1:1 as eluent) to obtain 0.066 g of colorless oily liquid compound 8 (0.212 mmol). The yield of compound 8 is 79%. The mass spectrometry and nuclear magnetic resonance spectra of compound 8 are as follows: 1 H NMR (600 MHz, CDCl3) δ7.92 (d, J = 7.8 Hz, 2H), 7.36 (d, J = 7.8 Hz, 2H), 4.15 (t, J = 5.7 Hz, 1H), 4.03(q, J= 7.0 Hz, 2H), 3.91-3.81 (m, 5H), 3.76-3.70 (m, 2H), 2.50-2.40 (m, 2H),1.16 (t, J = 7.1 Hz, 3H). 13 C NMR (151 MHz, CDCl3) δ 172.05, 166.94, 143.79,129.82, 129.78, 127.89, 69.79, 66.55, 63.99, 60.77, 52.21, 34.29, 14.20. HRMS(ESI) Calcd for [C 15 H 21 [NNaO6, M+Na] + : 334.1261; Found: 334.1256. The reaction equation is as follows: .

[0055] Obviously, those skilled in the art can make various modifications and variations to this invention without departing from its spirit and scope. If such modifications and variations fall within the scope of equivalents of this invention, then this invention also intends to include these modifications and variations.

Claims

1. A method for preparing an organoboron reagent α-boronyl oxime compound, characterized in that, Includes the following steps: Under blue light irradiation at room temperature, with thiol R 8 SH is a catalyst for olefins, N - A heterocyclic carbene borane adduct was reacted with a nitroso compound in an organic solvent for 30-48 h to obtain an α-boron oxime compound with the structural formula shown in formula (Ⅰ); Among them, R 2 It is H or alkyl; R 3 It is an alkyl or substituted aryl group; R 4 It is H, alkyl, or halogen; R 5 R 6 R 7 R 8 All are alkyl groups or alkyl groups substituted with functional groups.

2. The method for preparing the organoboron reagent α-boronyl oxime compound according to claim 1, characterized in that, The olefin, N The molar ratio of the heterocyclic carbene borane adduct to the nitroso compound is 1:3:

2.

3. The method for preparing the organoboron reagent α-boronyl oxime compound according to claim 1, characterized in that, The catalyst has a molar ratio of thiol to olefin of (0.2~0.5):

1.

4. The method for preparing the organoboron reagent α-boronyl oxime compound according to claim 1, characterized in that, The wavelength of the blue light irradiation is 437~471nm.

5. The method for preparing the organoboron reagent α-boronyl oxime compound according to claim 1, characterized in that, The structural formula of the olefin is shown in formula (II); N The structural formula of the heterocyclic carbene borane adduct is shown in formula (III); the structural formula of the nitroso compound is shown in formula (IV) or formula (V); the organic solvent is tetrahydrofuran, dioxane, ethyl acetate, benzene, toluene, trifluorotoluene, acetonitrile, benzonitrile, dichloromethane, 1,2-dichloroethane, N , N - any one or more of dimethylformamide, acetone, methanol, ethanol, and isopropanol; Among them, R 1 It is an aryl group with optional substitution, or an electron-withdrawing functional group; R 5 R 6 R 7 R 8 All are alkyl groups or alkyl groups substituted with functional groups.

6. The method for preparing the organoboron reagent α-boronyl oxime compound according to claim 5, characterized in that, The optionally substituted aryl group is any one or more selected from phenyl, substituted phenyl, naphthyl, furan, thiophene, pyridyl, or indole; the other electron-withdrawing functional group is any one or more selected from ester, amide, cyano, or sulfonyl; the alkyl group is C1-C6. 12 Alkyl; wherein the substituents in the substituted phenyl group are C1-C2. 12 Alkyl, C1~C 12 Alkoxy, C1~C 12 Alkylthio group, C2~C 12 Acyloxy group, silicon group, hydroxyl group, cyano group, sulfonyl group, acetal, trifluoromethyl group, halogen, (C1~C) 12 alkyl)amino, di(C1~C) 12 Alkyl)amino, C1~C 12 Acyl group, C2~C 12 Ester group, di(C1~C) 12 Any one or more of the alkyl) amide groups.

7. The method for preparing the organoboron reagent α-boronyl oxime compound according to claim 6, characterized in that, The C1~C 12 The alkyl group is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, neohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, neoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, neooctyl, sec-octyl, or tert-octyl; the C1~C 12 The acyl group is formyl, acetyl, propionyl, n-butyryl, isobutyryl, n-valeryl, isovaleryl, sec-valeryl, neovaleryl, n-hexanoyl, isohexanoyl, neohexanoyl, sec-hexanoyl, n-heptanoyl, isoheptanoyl, neoheptanoyl, sec-heptanoyl, n-octanoyl, isooctanoyl, neooctanoyl, sec-octanoyl, 1-cyclopropylformyl, 1-cyclobutylformyl, 1-cyclopentylformyl, 1-cyclohexylformyl, 1-cycloheptylformyl.

8. The method for preparing the organoboron reagent α-boronyl oxime compound according to claim 6, characterized in that, The C2~C 12 Acyloxy groups are acetyloxy, propionyloxy, n-butyryloxy, isobutyryloxy, n-valeryloxy, isovaleryloxy, sec-valeryloxy, neovaleryloxy, n-hexanoyloxy, isohexanoyloxy, neohexanoyloxy, sec-hexanoyloxy, n-heptanoyloxy, isoheptanoyloxy, neoheptanoyloxy, sec-heptanoyloxy, n-octanoyloxy, isooctanoyloxy, neooctanoyloxy, sec-octanoyloxy, 1-cyclopropylformyloxy, 1-cyclobutylformyloxy, 1-cyclopentylformyloxy, 1-cyclohexylformyloxy, 1-cycloheptylformyloxy; wherein C2~C 12 The ester group is methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, n-pentoxycarbonyl, isopentoxycarbonyl, neopentoxycarbonyl, secondary pentoxycarbonyl, tertiary pentoxycarbonyl, cyclopentoxycarbonyl, n-hexyloxycarbonyl, isohexyloxycarbonyl, neohexyloxycarbonyl, secondary hexyloxycarbonyl, tertiary hexyloxycarbonyl, cyclohexyloxycarbonyl, n-heptoxycarbonyl, isoheptoxycarbonyl, neoheptoxycarbonyl, secondary hexyloxycarbonyl, tertiary hexyloxycarbonyl, cycloheptoxycarbonyl.

9. An organoboron reagent α-boronyl oxime compound prepared by the preparation method according to any one of claims 1 to 8.

10. The use of an organoboron reagent α-boronyl oxime compound as described in claim 9 in the preparation of amino alcohol compounds.

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