Method for synthesis of 2-aryl-2h-benzotriazole compounds driven by visible light and applications thereof

Abstract

The application belongs to the technical field of organic compound preparation, and discloses a method for synthesizing 2-aryl-2H-benzotriazole compounds under visible light driving and application thereof. The synthesis method comprises the following steps: mixing ortho-nitro azobenzene compound, boronate ester, 4-cyanopyridine and organic solvent, performing reaction under visible light irradiation, removing the organic solvent, and separating to obtain 2-aryl-2H-benzotriazole compounds. In the application, the ortho-nitro azobenzene compound is used as a basic raw material, the boronate ester and the 4-cyanopyridine are added, and under the condition that no metal catalyst is used, the 2-aryl-2H-benzotriazole compound product with a yield of not less than 74% can be obtained within a reaction time of less than 1 hour under visible light with a wavelength of not more than 450 nm. Meanwhile, the method of the application shows wide substrate applicability, and various types of ortho-nitro azobenzene compounds can be converted into 2-aryl-2H-benzotriazole compounds.

Description

Technical Field

[0001] This invention belongs to the field of organic compound preparation technology, and specifically relates to a method for the visible light-driven synthesis of 2-aryl-2H-benzotriazole compounds and its application. Background Technology

[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. Currently, the methods for preparing 2-aryl-2H-benzotriazoles are mainly divided into two categories: (1) arylation reaction of N-unsubstituted benzotriazoles; (2) cyclization reaction of 2-substituted azobenzene.

[0003] In the first type of method, N 1，3 -N 2 Regioselectivity between sites is a common and serious challenge, and reactions often fail to yield a single product. Therefore, compared to the first type of method, the second type of method is more common and practical because it avoids the regioselectivity problem. The second type of method can be divided into the following main types: (1) thermal decomposition reaction of 2-azidoazo aromatics; (2) reductive cyclization reaction of 2-nitroazo aromatics; (3) oxidative cyclization reaction of 2-aminoazobenzene; (4) cascade reaction of 2-haloazo aromatics with compounds such as azides. Although the regioselectivity problem can be avoided, most of these methods require the use of transition metal catalysts or highly complex organic catalytic systems, and the reactions need to be carried out at high temperatures and for long reaction times.

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

[0005] The present invention aims to at least solve one of the technical problems existing in the prior art. To this end, the present invention proposes a method for the visible light-driven synthesis of 2-aryl-2H-benzotriazole compounds and its application. The method not only eliminates the need for a metal catalyst, but also synthesizes 2-aryl-2H-benzotriazole compounds at room temperature by visible light irradiation, with a short reaction time of only 30 minutes and a high product yield of not less than 74%.

[0006] The inventive concept of this invention is as follows: Using o-nitroazobenzene compounds as a base material, and adding borate ester and 4-cyanopyridine, a 2-aryl-2H-benzotriazole compound product can be obtained in less than 1 hour at room temperature and under visible light irradiation without a metal catalyst, with a yield of not less than 74%. Furthermore, the synthetic method of this invention demonstrates broad substrate applicability, enabling the conversion of various types of o-nitroazobenzene compounds into 2-aryl-2H-benzotriazole compounds.

[0007] The first aspect of this invention provides a method for synthesizing a 2-aryl-2H-benzotriazole compound, comprising the following steps:

[0008] The 2-aryl-2H-benzotriazole compound was prepared by mixing o-nitroazobenzene compound, diboronic acid ester, 4-cyanopyridine and an organic solvent, reacting under visible light irradiation, removing the organic solvent, and separating the mixture.

[0009] Preferably, the wavelength of the visible light does not exceed 450 nm; more preferably, the wavelength of the visible light is 400-450 nm.

[0010] Preferably, the reaction time is less than 1 hour; more preferably, the reaction time is 20-40 minutes.

[0011] Preferably, the general structural formula of the o-nitroazobenzene compound is: Ar 1 -N=N-Ar 2 Among them, Ar 1 Ar is an ortho-nitro-substituted aryl group. 2 It is an aryl group.

[0012] Preferably, the aryl group is an aromatic ring with 6-16 carbon atoms; more preferably, the aryl group is selected from at least one of phenyl, naphthyl, and pyrene.

[0013] Preferably, the aryl group has one or more substituent groups, and each of the substituent groups is independently selected from any one of alkyl, halogen, alkoxy, ester, trifluoromethoxy, and phenyl groups. That is, when there are multiple substituent groups, the substituent groups can be the same or different.

[0014] Preferably, the alkyl and alkoxy groups have 1-15 carbon atoms; more preferably, the alkyl and alkoxy groups have 2-8 carbon atoms.

[0015] Preferably, the structural formula of the o-nitroazobenzene compound is selected from any one of the following:

[0016]

[0017] Preferably, the borate ester is a di-catechol borate ester.

[0018] Preferably, the molar ratio of the o-nitroazobenzene compound, the diboronate ester, and 4-cyanopyridine is 1:(4-6):(0.05-0.5); more preferably, the molar ratio of the o-nitroazobenzene compound, the diboronate 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; more 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 involves simultaneously adding and mixing all components, or mixing in stages.

[0022] Preferably, the reaction is carried out under closed conditions, inert atmosphere (e.g., nitrogen, argon), and under visible light irradiation.

[0023] Preferably, the removal of organic solvents is carried out by rotary evaporation.

[0024] Preferably, the separation and purification are performed using column chromatography.

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

[0026]

[0027] The second aspect of the present invention provides the application of the above-described method for synthesizing the 2-aryl-2H-benzotriazole compound in the field of organic synthesis.

[0028] Preferably, the application includes applications in the fields of pharmaceuticals, ligands, ultraviolet stabilizers, or the synthesis of organic electronic materials.

[0029] Compared with the prior art, the above-described technical solution of the present invention has at least the following technical effects or advantages:

[0030] This invention uses o-nitroazobenzene compounds as a base material, adds di-catechol borate ester and 4-cyanopyridine, and, without a metal catalyst, under visible light-driven conditions, can produce 2-aryl-2H-benzotriazole compounds in yields of not less than 74% in less than 1 hour. Furthermore, the synthetic method of this invention exhibits broad substrate applicability, enabling the conversion of various types of o-nitroazobenzene compounds into 2-aryl-2H-benzotriazole compounds. Detailed Implementation

[0031] The present invention will now be described in detail with reference to embodiments to facilitate understanding of the invention by those skilled in the art. It is important to note that the embodiments are merely illustrative and should not be construed as limiting the scope of protection of the invention. Non-essential improvements and adjustments made to the invention by those skilled in the art based on the above description should still fall within the scope of protection of the invention. Furthermore, all raw materials mentioned below, unless otherwise specified, are commercially available products; all process steps or synthesis methods not mentioned in detail are process steps or synthesis methods known to those skilled in the art.

[0032] Example 1: Preparation of 2-aryl-2H-benzotriazole compounds

[0033] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0034]

[0035] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0036] In a glove box under nitrogen atmosphere, 0.8 mmol of bis(2-catechol borate) ester (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran organic solvent, and 0.2 mmol of (E)-1-(4-methyl-2-nitrophenyl)-2-(p-toluene)diazepine were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation and stirring for 30 minutes. A 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 purified by column chromatography using a mixture of n-hexane and ethyl acetate (50:1 v / v). The product 5-methyl-2-(p-toluyl)-2H-benzo[d][1,2,3]triazole was obtained with a yield of 98%.

[0037] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows:

[0038] 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);

[0039] 13 C NMR(101MHz, CDCl3)δ145.42(s),143.63(s),138.83(s),138.24(s),137.1 3(s),129.92(s),120.33(s),117.67(s),116.45(s),22.15(s),21.13(s).

[0040] Example 2: Preparation of 2-aryl-2H-benzotriazole compounds

[0041] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0042]

[0043] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0044] In a glove box under nitrogen atmosphere, 0.8 mmol of bis(2-catechol borate) ester (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)diazepine were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation and stirring for 30 minutes. A 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 purified by column chromatography. The developing solvent used in the purification process was a mixed solution of n-hexane / ethyl acetate (volume ratio 20:1). The product 5-bromo-2-(4-bromophenyl)-2H-benzo[d][1,2,3]triazole was obtained with a yield of 82%.

[0045] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows:

[0046] 1 H 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);

[0047] 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).

[0048] Example 3: Preparation of 2-aryl-2H-benzotriazole compounds

[0049] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0050]

[0051] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0052] In a glove box under nitrogen atmosphere, 0.8 mmol of bis(2-catechol)boronic acid ester (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran organic solvent, and 0.2 mmol of (E)-4-((4-(ethoxycarbonyl)phenyl)diazepine)-3-nitrobenzoate ethyl ester were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation and stirring for 30 minutes. A 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 purified by column chromatography using a hexane / ethyl acetate (20:1 v / v) mixture as the developing solvent. The product 2-(4-(ethoxycarbonyl)phenyl)-2H-benzo[d][1,2,3]triazole-5-carboxylic acid ethyl ester was obtained with a yield of 92%.

[0053] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows:

[0054] 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);

[0055] 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).

[0056] Example 4: Preparation of 2-aryl-2H-benzotriazole compounds

[0057] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0058]

[0059] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0060] In a glove box under nitrogen atmosphere, 0.8 mmol of bis(2-catechol borate) ester (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran organic solvent, and 0.2 mmol of (E)-1-(5-chloro-2-nitrophenyl)-2-(3-chlorophenyl)diazepine were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation and stirring for 30 minutes. A 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 purified by column chromatography using a mixture of n-hexane and ethyl acetate (50:1 v / v). The product 5-chloro-2-(3-chlorophenyl)-2H-benzo[d][1,2,3]triazole was obtained with a yield of 91%.

[0061] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows:

[0062] 1 H 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);

[0063] 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).

[0064] Example 5: Preparation of 2-aryl-2H-benzotriazole compounds

[0065] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0066]

[0067] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0068] In a glove box under nitrogen atmosphere, 0.8 mmol of bis(2-catechol borate) ester (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran organic solvent, and 0.2 mmol of (E)-1-(3,5-dimethyl-2-nitrophenyl)-2-(3,5-dimethylphenyl)diazepine were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation and stirring for 30 minutes. A 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 purified by column chromatography using a hexane / ethyl acetate (50:1 v / v) mixture as the developing solvent. The product 2-(3,5-dimethylphenyl)-4,6-dimethyl-2H-benzo[d][1,2,3]triazole was obtained with a yield of 89%.

[0069] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows:

[0070] 1 H 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);

[0071] 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).

[0072] Example 6: Preparation of 2-aryl-2H-benzotriazole compounds

[0073] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0074]

[0075] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0076] In a glove box under a nitrogen atmosphere, 0.8 mmol of bis(catechol) boronic acid ester (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran organic solvent, and 0.2 mmol of (E)-1-(2-nitro-4-(trifluoromethoxy)phenyl)-2-(4-(trifluoromethoxy)phenyl)diazepine were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation 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 then 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 50:1). The product 5-(trifluoromethoxy)-2-(4-(trifluoromethoxy)phenyl)-2H-benzo[d][1,2,3]triazole was obtained with a yield of 79%.

[0077] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows:

[0078] 1 H(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);

[0079] 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).

[0080] Example 7: Preparation of 2-aryl-2H-benzotriazole compounds

[0081] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0082]

[0083] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0084] In a glove box under a nitrogen atmosphere, 0.8 mmol of bis(catechol) boronic acid ester (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran organic solvent, and 0.2 mmol of (E)-1-(4-(tert-butyl)-2-nitrophenyl)-2-(4-(tert-butyl)phenyl)diazepine were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation 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 then 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 50:1). The product 5-(tert-butyl ester)-2-(4-(tert-butyl)phenyl)-2H-benzo[d][1,2,3]triazole was obtained with a yield of 74%.

[0085] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows: 113C 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).

[0086] Example 8: Preparation of 2-aryl-2H-benzotriazole compounds

[0087] The reaction equations for the preparation of 2-aryl-2H-benzotriazole compounds (showing only the target product) are as follows:

[0088]

[0089] A method for preparing 2-aryl-2H-benzotriazole compounds from o-nitroazobenzene compounds includes the following steps:

[0090] In a glove box under nitrogen atmosphere, 0.8 mmol of bis(1,1'-biphenyl)-4-yl)-2-(2-nitrophenyl)diazepine, 0.1 mmol of 4-cyanopyridine, 2.0 mL of tetrahydrofuran, and 0.2 mmol of (E)-1-([1,1'-biphenyl]-4-yl)-2-(2-nitrophenyl)diazepine were added sequentially to a 10 mL quartz tube equipped with a stir bar. The mixture was then removed from the glove box and placed in a photoreactor with a wavelength of 450 nm for irradiation and stirring for 30 minutes. A 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 purified by column chromatography using a hexane / ethyl acetate (50:1 v / v) mixture as the developing solvent. The product 2-([1,1'-biphenyl]-4-yl)-2H-benzo[d][1,2,3]triazole was obtained with a yield of 76%.

[0091] The characterization results of the proton and carbon NMR spectra of the product obtained in this embodiment are as follows:

[0092] 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);

[0093] 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).

[0094] For those skilled in the art, several simple deductions or substitutions can be made without departing from the inventive concept, without requiring creative effort. Therefore, any simple improvements made to this invention by those skilled in the art based on the disclosure of this invention should be within the scope of protection of this invention. The above embodiments are preferred embodiments of this invention, and all processes similar to this invention and equivalent changes should fall within the scope of protection of this invention.

Claims

1. A method for synthesizing 2-aryl-2H-benzotriazole compounds, characterized in that, Includes the following steps: The 2-aryl-2H-benzotriazole compound was prepared by mixing o-nitroazobenzene compound, diboronic acid ester, 4-cyanopyridine and organic solvent, reacting under visible light irradiation, removing the organic solvent and separating the mixture. The general structural formula of the o-nitroazobenzene compounds is: Ar 1 N = N Ar 2 Among them, Ar 1 Ar is a phenyl group containing an ortho-nitro-substituted group. 2 It is a phenyl group containing substituents; the substituents are independently selected from any one of C1-C8 alkyl, halogen, C1-C8 alkoxy, trifluoromethoxy, and phenyl.

2. A method for synthesizing 2-aryl-2H-benzotriazole compounds, characterized in that, Includes the following steps: The 2-aryl-2H-benzotriazole compound was prepared by mixing o-nitroazobenzene compound, diboronic acid ester, 4-cyanopyridine and organic solvent, reacting under visible light irradiation, removing the organic solvent and separating the mixture. The structural formula of the o-nitroazobenzene compound is selected from any one of the following: 、 、 、 、 、 、 、 ； The structural formula of the 2-aryl-2H-benzotriazole compound is selected from any one of the following: 、 、 、 、 、 、 、 。 3. The method for synthesizing 2-aryl-2H-benzotriazole compounds according to claim 1 or 2, characterized in that, The wavelength of the visible light does not exceed 450 nm; and / or the reaction time is less than 1 hour.

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

5. The application of the method for synthesizing 2-aryl-2H-benzotriazole compounds according to any one of claims 1 to 4 in the field of organic synthesis.

6. The application according to claim 5, characterized in that, The applications include those in the fields of pharmaceuticals, ligands, UV stabilizers, or the synthesis of organic electronic materials.

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