Method for synthesizing 2-aryl-2h-benzotriazole compound under driving of visible light, and use thereof

Abstract

A method for synthesizing a 2-aryl-2H-benzotriazole compound under driving of visible light, and a use thereof. The synthesis method comprises the following steps: mixing an o-nitroazobenzene compound, bis(boronic ester), 4-cyanopyridine, and an organic solvent, reacting under the illumination of visible light, removing the organic solvent, and separating to obtain a 2-aryl-2H-benzotriazole compound. According to the present method, the o-nitroazobenzene compound is used as a basic raw material, bis(boronic ester) and 4-cyanopyridine are added, and under the condition that there is no metal catalyst and the wavelength of visible light does not exceed 450 nm, reaction is performed for less than one hour, so that the 2-aryl-2H-benzotriazole compound product with the yield not lower than 74% can be prepared. Moreover, the substrate adaptability of the present method is broad, and various o-nitroazobenzene compounds can be converted into the 2-aryl-2H-benzotriazole compounds.

Description

Visible light driven synthesis method of 2-aryl-2H-benzotriazole compounds and its application Technical Field

[0001] The present invention belongs to the technical field of organic compound preparation, and particularly relates to a method for synthesizing a 2-aryl-2H-benzotriazole compound driven by visible light and its application. Background Art

[0002] 2-Aryl-2H-benzotriazoles are important nitrogen-containing heterocyclic compounds. Due to their high activity, interesting structures, and anticancer properties, they have been widely used in materials science, synthetic organic chemistry, medicinal chemistry, and agricultural chemistry. Current methods for preparing 2-aryl-2H-benzotriazoles can be divided into two main categories: (1) arylation of N-unsubstituted benzotriazoles and (2) cyclization of 2-substituted azobenzenes.

[0003] In the first method, N 1，3 -N 2 Regioselectivity between positions is a common and severe challenge, and the reaction often does not produce a single product. Therefore, compared with the first type of method, the second type of method is more common and more practical because it can avoid the regioselectivity problem. The second type of method can be divided into the following main types: (1) thermal decomposition reaction of 2-azidoazoarenes; (2) reductive cyclization reaction of 2-nitroazoarenes; (3) oxidative cyclization reaction of 2-aminoazobenzene; (4) cascade reaction of 2-halogenated azoarenes with compounds such as azides. Although these methods can avoid the regioselectivity problem, most of them require the use of transition metal catalysts or highly complex organic catalytic systems, and the reactions also need to be carried out at higher temperatures and longer reaction times.

[0004] Therefore, there is an urgent need to provide a new synthesis method for 2-aryl-2H-benzotriazole compounds, which not only does not require the use of metal catalysts, but also does not require heating. It only requires visible light illumination at room temperature, and has a short reaction time and high product yield.

[0005] Summary of the Invention

[0006] The present invention aims to address at least one of the technical problems existing in the above-mentioned prior art. To this end, the present invention provides a method for the visible light-driven synthesis of 2-aryl-2H-benzotriazole compounds and their application. The method not only eliminates the need for metal catalysts but also allows the synthesis of 2-aryl-2H-benzotriazole compounds at room temperature via visible light irradiation. The reaction time is short, requiring only 30 minutes, and the product yield is high, with a yield of no less than 74%.

[0007] The present invention is based on an o-nitroazobenzene compound as a base material, with the addition of a biboronic acid ester and 4-cyanopyridine. In the absence of a metal catalyst, at room temperature and under visible light irradiation, a reaction time of less than one hour can produce a 2-aryl-2H-benzotriazole compound with a yield of no less than 74%. Furthermore, the synthesis method of the present invention exhibits broad substrate applicability, enabling the conversion of various types of aromatic o-nitroazobenzene compounds into 2-aryl-2H-benzotriazole compounds.

[0008] The first aspect of the present invention provides a method for synthesizing a 2-aryl-2H-benzotriazole compound, comprising the following steps:

[0009] An o-nitroazobenzene compound, a biboronic acid ester, 4-cyanopyridine and an organic solvent are mixed, reacted under visible light illumination, and the organic solvent is removed and separated to obtain the 2-aryl-2H-benzotriazole compound.

[0010] Preferably, the wavelength of the visible light does not exceed 450 nm; further preferably, the wavelength of the visible light is 400-450 nm.

[0011] Preferably, the reaction time is less than 1 hour; more preferably, the reaction time is 20-40 minutes.

[0012] Preferably, the o-nitroazobenzene compound has the general structural formula: Ar 1 -N=N-Ar 2 Among them, Ar 1 is an o-nitro-substituted aryl group, Ar 2 It is an aryl group.

[0013] Preferably, the aryl group is an aromatic ring of 6-16 carbon atoms; further preferably, the aryl group is at least one selected from phenyl, naphthyl, and pyrenyl.

[0014] Preferably, the aryl group carries one or more substituents, each of which is independently selected from any one of an alkyl group, a halogen group, an alkoxy group, an ester group, a trifluoromethoxy group, and a phenyl group. In other words, when there are multiple substituents, each substituent may be the same or different.

[0015] Preferably, the number of carbon atoms in the alkyl group and the alkoxy group is 1-15; more preferably, the number of carbon atoms in the alkyl group and the alkoxy group is 2-8.

[0016] Preferably, the structural formula of the o-nitroazobenzene compound is selected from any one of the following:

[0017] Preferably, the biborate is bis(bis-catechol) borate.

[0018] Preferably, the molar ratio of the o-nitroazobenzene compound, the borate ester and 4-cyanopyridine is 1:(4-6):(0.05-0.5); further preferably, the molar ratio of the o-nitroazobenzene compound, the borate ester and 4-cyanopyridine is 1:(3-5):(0.3-0.5).

[0019] Preferably, the organic solvent is selected from at least one of tetrahydrofuran (THF), acetonitrile (MeCN), methanol (MeOH), and ethanol; more preferably, the organic solvent is tetrahydrofuran.

[0020] Preferably, the molar volume ratio of the o-nitroazobenzene compound to the organic solvent is 0.2 mmol: (1-5) mL; further preferably, the molar volume ratio of the o-nitroazobenzene compound to the organic solvent is 0.2 mmol: (1-2) mL.

[0021] Preferably, the mixing process is to mix the components simultaneously or in steps.

[0022] Preferably, the reaction is carried out under sealed conditions, in an inert atmosphere (eg, nitrogen, argon), and under visible light illumination.

[0023] Preferably, the organic solvent is removed by rotary evaporation.

[0024] Preferably, the separation is performed by column chromatography.

[0025] Preferably, the structural formula of the 2-aryl-2H-benzotriazole compound is selected from any one of the following:

[0026] The second aspect of the present invention provides the application of the synthesis method of the above-mentioned 2-aryl-2H-benzotriazole compound in the field of organic synthesis.

[0027] Preferably, the application includes application in the fields of medicine, ligand, ultraviolet stabilizer or organic electronic material synthesis.

[0028] Compared with the prior art, the above technical solution of the present invention has at least the following technical effects or advantages:

[0029] The present invention uses an o-nitroazobenzene compound as a base raw material, adds bis(bis-catechol borate) and 4-cyanopyridine, and, in the absence of a metal catalyst and driven by visible light, produces a 2-aryl-2H-benzotriazole compound with a yield of no less than 74% in less than one hour. Furthermore, the synthesis method of the present invention exhibits broad substrate applicability, enabling the conversion of various o-nitroazobenzene compounds into 2-aryl-2H-benzotriazole compounds. DETAILED DESCRIPTION

[0030] The present invention is described in detail below with reference to the examples to facilitate understanding of the present invention by those skilled in the art. It is necessary to point out that the examples are only used to further illustrate the present invention and are not to be construed as limiting the scope of the present invention. Non-essential improvements and adjustments made to the present invention by those skilled in the art based on the above-mentioned invention should still fall within the scope of the present invention. At the same time, the raw materials mentioned below that are not described in detail are all commercially available products; the process steps or synthesis methods not mentioned in detail are all process steps or synthesis methods known to those skilled in the art.

[0031] Example 1: Preparation of 2-aryl-2H-benzotriazole compounds

[0032] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0033] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0034] In a nitrogen-filled glove box, 0.8 mmol of bis(bis(phthalocyano)benzene) boronate (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran (2.0 mL of the organic solvent), and 0.2 mmol of (E)-1-(4-methyl-2-nitrophenyl)-2-(p-toluene)diazene were added to a 10 mL quartz tube equipped with a stirrer. The mixture was removed from the glove box and placed in a photoreactor illuminated at 450 nm with stirring for 30 minutes. One spoonful of 300-400 mesh silica gel was then added, and the organic solvent was removed under reduced pressure. The reaction product was adsorbed onto the silica gel and separated and purified by column chromatography using a mixture of n-hexane and ethyl acetate (50:1 by volume) as the developing solvent. The product, 5-methyl-2-(p-tolyl)-2H-benzo[d][1,2,3]triazole, was isolated and purified in a 98% yield.

[0035] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows:

[0036] 1 H NMR (400MHz, CDCl3) δ8.20-8.14(m,2H),7.78(d,J=8.7Hz,1H),7.63(s,1H),7.31(d,J=7.9Hz,2H),7.21(s,1H),2.48(s,3H),2.41(s,3H);

[0037] 13 C NMR(101MHz, CDCl3)δ145.42(s),143.63(s),138.83(s),138.24(s),137.13(s), 129.92(s),120.33(s),117.67(s),116.45(s),22.15(s),21.13(s).

[0038] Example 2: Preparation of 2-aryl-2H-benzotriazole compounds

[0039] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0040] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0041] In a glove box under a nitrogen atmosphere, 0.8 mmol of bis(bis(bis-catechol) borate (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran (organic solvent), and 0.2 mmol of (E)-1-(4-bromo-2-nitrophenyl)-2-(4-bromophenyl)diazene were added sequentially to a 10 mL quartz tube equipped with a stirrer. The mixture was removed from the sealed quartz tube and placed in a photoreactor with a wavelength of 450 nm for 30 minutes of illumination and stirring. One spoonful of 300-400 mesh silica gel was then added, and the organic solvent was removed under reduced pressure. The reaction product was adsorbed onto the silica gel and separated and purified by column chromatography using a mixed solution of n-hexane / ethyl acetate (volume ratio 20:1) as the developing solvent. The product, 5-bromo-2-(4-bromophenyl)-2H-benzo[d][1,2,3]triazole, was isolated and obtained in an 82% yield.

[0042] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows:

[0043] 1H NMR (400MHz, CDCl3) δ8.22(d,J=8.3Hz,2H),8.10(s,1H),7.80(d,J=8.9Hz,1H),7.68(d,J=8.3Hz,2H),7.50(d,J=9.0Hz,1H);

[0044] 13 C NMR (101MHz, CDCl3) δ145.94(s), 143.72(s), 139.03(s), 132.63(s), 131.37(s), 123.24(s), 122.05(s), 121.19(s), 120.77(s), 119.73(s).

[0045] Example 3: Preparation of 2-aryl-2H-benzotriazole compounds

[0046] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0047] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0048] In a glove box under a nitrogen atmosphere, 0.8 mmol of bis(bis(phthalocyanol)boronic acid) ester (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran (2.0 mL of the organic solvent), and 0.2 mmol of ethyl (E)-4-((4-(ethoxycarbonyl)phenyl)diazenyl)-3-nitrobenzoate were added to a 10 mL quartz tube equipped with a stirrer. The mixture was then removed from the glove box and placed in a photoreactor illuminated at a wavelength of 450 nm with stirring for 30 minutes. One spoonful of 300-400 mesh silica gel was then added, and the organic solvent was removed under reduced pressure. The reaction product was adsorbed onto the silica gel and separated and purified by column chromatography using a mixed solution of n-hexane / ethyl acetate (volume ratio 20:1) as the developing solvent. The product, ethyl 2-(4-(ethoxycarbonyl)phenyl)-2H-benzo[d][1,2,3]triazole-5-carboxylate, was isolated and obtained in a yield of 92%.

[0049] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows:

[0050] 1H NMR (400MHz, CDCl3) δ8.73(s,1H),8.47(d,J=7.4Hz,2H),8.25(d,J=7.7Hz,2H),8.09(d ,J=9.1Hz,1H),7.97(d,J=8.8Hz,1H),4.47-4.41(m,4H),1.44(dt,J=10.8,5.5Hz,6H);

[0051] 13 C NMR(101MHz, CDCl3)δ166.02(s),165.57(s),146.93(s),144.77(s),142.98(s),131.26(s),131. 01(s),129.96(s),127.61(s),122.08(s),120.51(s),118.41(s),61.44(d,J=5.4Hz),14.31(s).

[0052] Example 4: Preparation of 2-aryl-2H-benzotriazole compounds

[0053] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0054] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0055] In a nitrogen-filled glove box, 0.8 mmol of bis(bis(di-pyrocatechol)boronic acid ester) (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran (the organic solvent), and 0.2 mmol of (E)-1-(5-chloro-2-nitrophenyl)-2-(3-chlorophenyl)diazene were added sequentially to a 10 mL quartz tube equipped with a stirrer. The mixture was removed from the glove box and placed in a photoreactor illuminated at 450 nm with stirring for 30 minutes. One spoonful of 300-400 mesh silica gel was then added, and the organic solvent was removed under reduced pressure. The reaction product was adsorbed onto the silica gel and separated and purified by column chromatography using a mixture of n-hexane and ethyl acetate (50:1 by volume) as the developing solvent. The product, 5-chloro-2-(3-chlorophenyl)-2H-benzo[d][1,2,3]triazole, was isolated and purified in a 91% yield.

[0056] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows:

[0057] 1H NMR (400MHz, CDCl3) δ8.37(s,1H),8.23(d,J=8.0Hz,1H),7.89(dd,J=19.0,5.1Hz,2H),7.46(dd,J=16.0,8.0Hz,2H),7.38(dd,J=9.1,1.7Hz,1H);

[0058] 13 C NMR(101MHz, CDCl3)δ145.37(s),143.58(s),140.88(s),135.40(s),133.41(s),130.52(s),129 .23(d,J=4.8Hz),120.89(s),119.63(s),118.62(s),117.40(s),77.31(s),77.00(s),76.68(s).

[0059] Example 5: Preparation of 2-aryl-2H-benzotriazole compounds

[0060] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0061] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0062] In a nitrogen-filled glove box, 0.8 mmol of bis(bis(dimethyl)-2-nitrophenyl)-1-(3,5-dimethylphenyl)-2-(3,5-dimethylphenyl)diazene was added, in sequence, to a 10 mL quartz tube equipped with a stirrer. The mixture was removed from the glove box and placed in a photoreactor illuminated at 450 nm with stirring for 30 minutes. One spoonful of 300-400 mesh silica gel was then added, and the organic solvent was removed under reduced pressure. The reaction product was adsorbed onto the silica gel and separated and purified by column chromatography using a mixture of n-hexane and ethyl acetate (50:1 by volume) as the developing solvent. The product, 2-(3,5-dimethylphenyl)-4,6-dimethyl-2H-benzo[d][1,2,3]triazole, was isolated and purified in an 89% yield.

[0063] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows:

[0064] 1H NMR (400MHz, CDCl3) δ7.98(d,J=16.8Hz,2H),7.47(s,1H),7.05(dd,J=21.2,12.4Hz,2H),2.67(d,J=12.2Hz,3H),2.50-2.44(m,9H);

[0065] 13 C NMR(101MHz, CDCl3)δ145.40(s),139.24(s),137.37(s),130.69(s),130.24(s),129.76(s),129.01(s),126 .96(s),118.45(s),118.24(s),113.66(s),77.32(s),77.00(s),76.68(s),22.16(s),21.34(s),17.08(s).

[0066] Example 6: Preparation of 2-aryl-2H-benzotriazole compounds

[0067] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0068] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0069] In a glove box under a nitrogen atmosphere, 0.8 mmol of bis(catechol) borate (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of an organic solvent, tetrahydrofuran, and 0.2 mmol of (E)-1-(2-nitro-4-(trifluoromethoxy)phenyl)-2-(4-(trifluoromethoxy)phenyl)diazene were added sequentially to a 10 mL quartz tube equipped with a stirrer, and the mixture was mixed to obtain a mixture. The sealed quartz tube was removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for illumination and stirring for 30 minutes. Then, a spoonful of 300-400 mesh silica gel was added, and the organic solvent was removed under reduced pressure. The reaction product was adsorbed onto the silica gel and separated and purified by column chromatography. The developing solvent used in the separation and purification process was a mixed solution of n-hexane / ethyl acetate (volume ratio of 50:1). The product 5-(trifluoromethoxy)-2-(4-(trifluoromethoxy)phenyl)-2H-benzo[d][1,2,3]triazole was separated with a yield of 79%.

[0070] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows:

[0071] 1H(400NMR MHz, CDCl3) δ 8.38 (d, J = 9.0 Hz, 2H), 7z, CDCl 3) δ 149.59 (s), 148.15 (s), 144.75 (s), 143.37 ( s09.09(s),.95(d,J=9.2Hz,1H),7.76(s,1H),7.40(d,J=8.7Hz,2H),7.30(d,J=9.2Hz,1H);

[0072] 13 C NMR (101MHz, CDCl3), 138.33 (s), 122.79 (s), 122.13-121.58 (m), 120.15 (s), 119.18 (d, J = 13.1Hz), 11MH 77.29 (s), 76.98 (s), 76.66 (s).

[0073] Example 7: Preparation of 2-aryl-2H-benzotriazole compounds

[0074] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0075] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0076] In a glove box under a nitrogen atmosphere, 0.8 mmol of bis(catechol) borate (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of an organic solvent, tetrahydrofuran, and 0.2 mmol of (E)-1-(4-(tert-butyl)-2-nitrophenyl)-2-(4-(tert-butyl)phenyl)diazene were added sequentially to a 10 mL quartz tube equipped with a stirrer, and the mixture was mixed to obtain a mixture. The sealed quartz tube was removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for illumination and stirring for 30 minutes. Then, a spoonful of 300-400 mesh silica gel was added, and the organic solvent was removed under reduced pressure. The reaction product was adsorbed onto the silica gel and separated and purified by column chromatography. The developing solvent used in the separation and purification process was a mixed solution of n-hexane / ethyl acetate (volume ratio of 50:1). The product 5-(tert-butyl)-2-(4-(tert-butyl)phenyl)-2H-benzo[d][1,2,3]triazole was separated with a yield of 74%.

[0077] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows: 1H NMR (400MHz, CDCl3) δ8.26(d,J=8.9Hz,2H),7.90-7.86(m,2H),7.56(dd,J=14.5,5.2Hz,3H),1.43(s,9H),1.40(s,9H); 13 C NMR(101MHz, CDCl3)δ152.04(s),150.35(s),145.34(s),143.48(s),138.12(s),126.80(s),126.30(s),12 0.07(s),117.55(s),112.74(s),77.34(s),77.02(s),76.70(s),35.32(s),34.80(s),31.31(s),31.09(s).

[0078] Example 8: Preparation of 2-aryl-2H-benzotriazole compounds

[0079] The reaction equation involved in preparing 2-aryl-2H-benzotriazole compounds (only the target product is reflected in the reaction equation) is as follows:

[0080] A method for preparing a 2-aryl-2H-benzotriazole compound from an o-nitroazobenzene compound comprises the following steps:

[0081] In a nitrogen-filled glove box, 0.8 mmol of bis(di-catechol) boronate (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran (2-nitrophenyl)diazene (0.2 mmol) were added sequentially to a 10 mL quartz tube equipped with a stirrer. The mixture was removed from the glove box and placed in a photoreactor illuminated at 450 nm with stirring for 30 minutes. One spoonful of 300-400 mesh silica gel was then added. The organic solvent was removed under reduced pressure, and the reaction product was adsorbed onto the silica gel. The product was then isolated and purified by column chromatography using a mixture of n-hexane and ethyl acetate (50:1 by volume) as the developing solvent. The product, 2-(1,1'-biphenyl)-4-yl-2H-benzo[d][1,2,3]triazole, was isolated in a 76% yield.

[0082] The characterization results of the hydrogen nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the product prepared in this example are as follows:

[0083] 1H NMR (400MHz, CDCl3) δ8.48-8.42(m,2H),8.00-7.85(m,2H),7.80(d,J=8.4Hz,2H),7.68(d,J=7.3Hz,2H),7.50(t,J=7.6Hz,2H),7.46-7.36(m,3H);

[0084] 13 C NMR(101MHz, CDCl3)δ145.10(s),141.91(s),139.85(s),128.94(s),128.0 4(s), 127.15(d,J=9.9Hz), 126.47(s), 121.20(s), 120.96(s), 118.35(s).

[0085] For those skilled in the art to which the present invention belongs, a number of simple deductions or substitutions can be made without departing from the concept of the present invention, without having to resort to creative work. Therefore, based on the disclosure of the present invention, simple improvements made by those skilled in the art to the present invention should be within the scope of protection of the present invention. The above embodiments are preferred embodiments of the present invention, and all processes similar to the present invention and equivalent changes made should fall within the scope of protection of the present invention.

Claims

1. A method for synthesizing a 2-aryl-2H-benzotriazole compound, characterized in that, Comprising the following steps: Mix an o-nitroazobenzene compound, a diborate, 4-cyanopyridine and an organic solvent, carry out a reaction under visible light irradiation, remove the organic solvent, and separate to obtain the 2-aryl-2H-benzotriazole compound.

2. The synthesis method of the 2-aryl-2H-benzotriazole compound according to claim 1, characterized in that, The wavelength of the visible light does not exceed 450 nm; and / or, the reaction time is less than 1 hour.

3. The synthesis method of the 2-aryl-2H-benzotriazole compound according to claim 1, characterized in that, The general structural formula of the o-nitroazobenzene compound is: Ar 1 -N=N-Ar 2 ; wherein, Ar 1 is an aryl group substituted with o-nitro, and Ar 2 is an aryl group.

4. The synthetic method of the 2-aryl-2H-benzotriazole compound according to claim 3, characterized in that, The aryl group is an aromatic ring having 6 to 16 carbon atoms.

5. The synthesis method of the 2-aryl-2H-benzotriazole compound according to claim 3, characterized in that, The aryl group is substituted with one or more substituents, and the multiple substituents are each independently selected from any one of an alkyl group, a halogen group, an alkoxy group, an ester group, a trifluoromethoxy group, and a phenyl group.

6. The synthesis method of the 2-aryl-2H-benzotriazole compound according to claim 3, characterized in that, The structural formula of the o-nitroazobenzene compound is selected from any one of the following:

7. The synthetic method of the 2-aryl-2H-benzotriazole compound according to claim 1, characterized in that, The molar ratio of the o-nitroazobenzene compound, the diborate and 4-cyanopyridine is 1:(4-6):(0.05-0.5).

8. The synthetic method of the 2-aryl-2H-benzotriazole compound according to claim 1, characterized in that, The structural formula of the 2-aryl-2H-benzotriazole compound is selected from any one of the following:

9. Use of the method for synthesizing a 2-aryl-2H-benzotriazole compound according to any one of claims 1 to 8 in the field of organic synthesis.

10. The application according to claim 9, wherein The use includes use in the fields of medicine, ligands, ultraviolet stabilizers or organic electronic material synthesis.

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