WO2025138874A1 - Method for synthesizing 2-aryl-2h-benzotriazole compound under driving of visible light, and use thereof - Google Patents

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

The invention belongs to the technical field of organic compound preparation, and particularly relates to a method for synthesizing 2-aryl-2H-benzotriazole compounds driven by visible light and applications thereof.

Background Art

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. The current methods for preparing 2-aryl-2H-benzotriazoles can be divided into two categories: (1) arylation of N-unsubstituted benzotriazoles and (2) cyclization of 2-substituted azobenzenes.

In the first type of method, the regioselectivity between the N1 ^{, 3} - ^N2 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 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 also need to be carried out at higher temperatures and longer reaction times.

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

Summary of the invention

The present invention aims to solve at least one of the technical problems existing in the above-mentioned prior art. To this end, the present invention provides a method for synthesizing 2-aryl-2H-benzotriazole compounds driven by visible light and its application, wherein the method does not require the use of a metal catalyst, and can synthesize 2-aryl-2H-benzotriazole compounds by visible light illumination at room temperature, and the reaction time is short, only 30 minutes; the product yield is high, and the yield is not less than 74%.

The inventive concept of the present invention is: the present invention uses o-nitroazobenzene compound as the basic raw material, adds biboric acid ester and 4-cyano In the absence of a metal catalyst, at room temperature and under visible light irradiation, a 2-aryl-2H-benzotriazole compound product with a yield of not less than 74% can be prepared after a reaction time of less than 1 hour. At the same time, the synthesis method of the present invention shows a wide substrate applicability, and various types of aromatic o-nitroazobenzene compounds can be converted into 2-aryl-2H-benzotriazole compounds.

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

The o-nitroazobenzene compound, biboric acid ester, 4-cyanopyridine and an organic solvent are mixed, reacted under visible light illumination, the organic solvent is removed, and the mixture is separated to obtain the 2-aryl-2H-benzotriazole compound.

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

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

Preferably, the o-nitroazobenzene compound has a general structural formula of: Ar ¹ -N=N-Ar ² ; wherein Ar ¹ is an aryl group substituted with an o-nitro group, and Ar ² is an aryl group.

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

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

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

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

Preferably, the biboric acid ester is bis(bis(di-ortho-catechol) borate.

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).

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.

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.

Preferably, the mixing process is that the components are mixed simultaneously or in steps.

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

Preferably, the removal of the organic solvent is carried out by rotary evaporation.

Preferably, the separation is performed by column chromatography.

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

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

Preferably, the application includes application in the fields of medicine, ligand, UV stabilizer or organic electronic material synthesis.

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

The invention uses an o-nitroazobenzene compound as a basic raw material, adds bis(bis(diphenyl)phenol borate) and 4-cyanopyridine, and in the absence of a metal catalyst, under visible light driving, after a reaction time of less than 1 hour, a 2-aryl-2H-benzotriazole compound product with a yield of not less than 74% can be prepared. At the same time, the synthesis method of the invention shows a wide substrate applicability, and various types of o-nitroazobenzene compounds can be converted into 2-aryl-2H-benzotriazole compounds.

DETAILED DESCRIPTION

The present invention is described in detail below in conjunction with the examples, so that the technical personnel of the relevant technical field can understand the present invention. It is necessary to point out here that the examples are only used to further illustrate the present invention and cannot be understood as limiting the scope of protection of the present invention. The non-essential improvements and adjustments made to the present invention by the skilled person in the relevant field according to the above invention content should still belong to the scope of protection 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.

Example 1: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8mmol of bis-catechol borate (B ₂ cat ₂ ), 0.1mmol of 4-cyanopyridine, 2.0mL of organic solvent tetrahydrofuran, and 0.2mmol of (E)-1-(4-methyl-2-nitrophenyl)-2-(p-toluene)diazene were added into a 10mL quartz tube equipped with a stirrer in sequence, and mixed to obtain a mixture. The sealed quartz tube was taken out from the glove box, placed in a photoreactor with a wavelength of 450nm for illumination and stirred for reaction 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 50:1), and the product 5-methyl-2-(p-tolyl)-2H-benzo[d][1,2,3]triazole was separated and obtained with a yield of 98%.

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:

¹ H NMR (400MHz, CDCl ₃ ) 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);

¹³ C NMR (101MHz, CDCl ₃ ) 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).

Example 2: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8 mmol of bis-catechol borate (B ₂ cat ₂ ), 0.1 mmol of 4-cyanopyridine, 2.0 mL of organic solvent tetrahydrofuran, and 0.2 mmol of (E)-1-(4-bromo-2-nitrophenyl)-2-(4-bromophenyl)diazene were added into a 10 mL quartz tube equipped with a stirrer in sequence, and mixed to obtain a mixture. The sealed quartz tube was taken out from the glove box, placed in a photoreactor with a wavelength of 450 nm for illumination and stirred for reaction 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 20:1), and the product 5-bromo-2-(4-bromophenyl)-2H-benzo[d][1,2,3]triazole was separated and obtained with a yield of 82%.

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:

¹ H NMR (400MHz, CDCl ₃ ) δ8.22 (d, J = 8.3 Hz, 2H), 8.10 (s, 1H), 7.80 (d, J = 8.9 Hz, 1H), 7.68 (d, J = 8.3 Hz, 2H), 7.50 (d, J = 9.0 Hz, 1H);

¹³ C NMR (101MHz, CDCl ₃ )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).

Example 3: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8 mmol of bis(bis(pyrocatechol) borate (B ₂ cat ₂ ), 0.1 mmol of 4-cyanopyridine, 2.0 mL of organic solvent tetrahydrofuran, 0.2 mmol of (E)-4-((4-(ethyl)- The mixture is mixed to obtain a mixture, and the sealed quartz tube is taken out from the glove box, and placed in a photoreactor with a wavelength of 450nm for illumination and stirring for 30 minutes. Then, a spoonful of 300-400 mesh silica gel is added, and the organic solvent is removed under reduced pressure, and the reaction product is adsorbed on the silica gel, and separated and purified by column chromatography. The developing solvent used in the separation and purification process is a mixed solution of n-hexane/ethyl acetate (volume ratio 20:1), and the product 2-(4-(ethoxycarbonyl)phenyl)-2H-benzo[d][1,2,3]triazole-5-carboxylic acid ethyl ester is separated and obtained, and the yield is 92%.

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:

¹ H NMR (400MHz, CDCl ₃ )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);

¹³ C NMR (101MHz, CDCl ₃ )δ166.02(s),165.57(s),146.93(s),144.77(s),142.98(s),131.26(s),131.01(s),12 9.96 (s), 127.61 (s), 122.08 (s), 120.51 (s), 118.41 (s), 61.44 (d, J = 5.4Hz), 14.31 (s).

Example 4: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8mmol of bis-catechol borate (B ₂ cat ₂ ), 0.1mmol of 4-cyanopyridine, 2.0mL of organic solvent tetrahydrofuran, and 0.2mmol of (E)-1-(5-chloro-2-nitrophenyl)-2-(3-chlorophenyl)diazene were added into a 10mL quartz tube equipped with a stirrer in sequence, and mixed to obtain a mixture. The sealed quartz tube was taken out from the glove box, placed in a photoreactor with a wavelength of 450nm for illumination and stirred for reaction 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 50:1), and the product 5-chloro-2-(3-chlorophenyl)-2H-benzo[d][1,2,3]triazole was separated and obtained with a yield of 91%.

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:

¹ H NMR (400MHz, CDCl ₃ ) δ8.37 (s, 1H), 8.23 (d, J = 8.0 Hz, 1H), 7.89 (dd, J = 19.0, 5.1 Hz, 2H), 7.46 (dd, J = 16.0, 8.0 Hz, 2H), 7.38 (dd, J = 9.1, 1.7 Hz, 1H);

¹³ C NMR (101MHz, CDCl ₃ )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).

Example 5: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8mmol of bis-catechol borate (B ₂ cat ₂ ), 0.1mmol of 4-cyanopyridine, 2.0mL of organic solvent tetrahydrofuran, and 0.2mmol of (E)-1-(3,5-dimethyl-2-nitrophenyl)-2-(3,5-dimethylphenyl)diazene were added to a 10mL quartz tube equipped with a stirrer in sequence, and mixed to obtain a mixture. The sealed quartz tube was taken out from the glove box, placed in a photoreactor with a wavelength of 450nm for illumination and stirred for reaction 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 on 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 50:1), and the product 2-(3,5-dimethylphenyl)-4,6-dimethyl-2H-benzo[d][1,2,3]triazole was separated and obtained with a yield of 89%.

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:

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

¹³ C NMR (101MHz, CDCl ₃ )δ145.40(s),139.24(s),137.37(s),130.69(s),130.24(s),129.76(s),129.01(s),126.96(s),1 18.45(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).

Example 6: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8 mmol of bis(bis(trifluoromethoxy)phenyl)borate (B2cat2), 0.1 mmol of 4-cyanopyridine, 2.0 mL of organic solvent tetrahydrofuran and 0.2 mmol of (E)-1-(2-nitro-4-(trifluoromethoxy)phenyl)-2-(4-(trifluoromethoxy)phenyl)diazepine were added in sequence into a 10 mL quartz tube equipped with a stirring bar and mixed to obtain a mixture. The sealed quartz tube was taken out from the glove box and placed in a photoreactor with a wavelength of 450 nm for illumination and stirring for reaction 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 and obtained with a yield of 79%.

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:

¹ H (400NMR MHz, CDCl ₃ ) δ8.38 (d, J＝9.0Hz, 2H), 7z, CDCl ₃ )δ149.59(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);

¹³ C NMR (101MHz, CDCl ₃ ), 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).

Example 7: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8 mmol of bis(bis(diphenyl)-pyrocatechol) borate (B ₂ cat ₂ ), 0.1 mmol of 4-cyanopyridine, 2.0 mL of organic solvent tetrahydrofuran, and 0.2 mmol of (E)-1-(4-(tert-butyl)-2-nitrophenyl)-2-(4-(tert-butyl)phenyl)diazene were added to a 10 mL quartz tube equipped with a stirrer in sequence, and mixed to obtain a mixture. The sealed quartz tube was taken out from the glove box, placed in a photoreactor with a wavelength of 450 nm for illumination and stirred for reaction for 30 minutes. Then, a spoonful of 300-400 mesh silica was added. The organic solvent was removed under reduced pressure, the reaction product was adsorbed onto 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), and the product 5-(tert-butyl)-2-(4-(tert-butyl)phenyl)-2H-benzo[d][1,2,3]triazole was separated, and the yield was 74%.

The characterization results of hydrogen and carbon nuclear magnetic resonance spectra of the product prepared in this example are as follows: ¹ H NMR (400 MHz, CDCl ₃ ) δ8.26 (d, J=8.9 Hz, 2H), 7.90-7.86 (m, 2H), 7.56 (dd, J=14.5, 5.2 Hz, 3H), 1.43 (s, 9H), 1.40 (s, 9H); ¹³ C NMR (101 MHz, CDCl ₃ )δ152.04(s),150.35(s),145.34(s),143.48(s),138.12(s),126.80(s),126.30(s),120.07(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).

Example 8: Preparation of 2-aryl-2H-benzotriazole compounds

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

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

In a glove box under nitrogen atmosphere, 0.8 mmol of bis-catechol borate (B ₂ cat ₂ ), 0.1 mmol of 4-cyanopyridine, 2.0 mL of organic solvent tetrahydrofuran, and 0.2 mmol of (E)-1-([1,1'-biphenyl]-4-yl)-2-(2-nitrophenyl)diazene were added to a 10 mL quartz tube equipped with a stirrer in sequence, and mixed to obtain a mixture. The sealed quartz tube was taken out from the glove box, placed in a photoreactor with a wavelength of 450 nm for illumination and stirred for reaction 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 on 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 50:1), and the product 2-([1,1'-biphenyl]-4-yl)-2H-benzo[d][1,2,3]triazole was separated and obtained with a yield of 76%.

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:

¹ H NMR (400MHz, CDCl ₃ )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);

¹³ C NMR (101MHz, CDCl ₃ )δ145.10(s),141.91(s),139.85(s),128.94(s),128.04(s),127.15(d,J=9.9Hz),126.47(s),121.20(s),120.96(s),118.35(s).

For ordinary technicians in the technical field to which the present invention belongs, they can make some simple deductions or substitutions without departing from the concept of the present invention, without having to go through creative work. The above embodiments are preferred embodiments of the present invention, and any process similar to the present invention and any equivalent changes made thereto should fall within the scope of protection of the present invention.

Claims (10)

A method for synthesizing a 2-aryl-2H-benzotriazole compound, characterized in that it comprises the following steps: The o-nitroazobenzene compound, biboric acid ester, 4-cyanopyridine and an organic solvent are mixed, reacted under visible light illumination, the organic solvent is removed, and the mixture is separated to obtain the 2-aryl-2H-benzotriazole compound. The method for synthesizing a 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. The method for synthesizing a 2-aryl-2H-benzotriazole compound according to claim 1, characterized in that the o-nitroazobenzene compound has a general structural formula of: Ar ¹ -N=N-Ar ² ; wherein Ar ¹ is an aryl group substituted with an o-nitro group, and Ar ² is an aryl group. The method for synthesizing a 2-aryl-2H-benzotriazole compound according to claim 3, wherein the aryl group is an aromatic ring with 6 to 16 carbon atoms. The method for synthesizing a 2-aryl-2H-benzotriazole compound according to claim 3, characterized in that the aryl group carries one or more substituent groups, and the multiple substituents are 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. The method for synthesizing a 2-aryl-2H-benzotriazole compound according to claim 3, wherein the structural formula of the o-nitroazobenzene compound is selected from any one of the following:
The method for synthesizing a 2-aryl-2H-benzotriazole compound according to claim 1, characterized in that the molar ratio of the o-nitroazobenzene compound, the biboronate and the 4-cyanopyridine is 1:(4-6):(0.05-0.5). The method for synthesizing a 2-aryl-2H-benzotriazole compound according to claim 1, wherein the 2- The structural formula of the aryl-2H-benzotriazole compound is selected from any one of the following:
Application of the method for synthesizing the 2-aryl-2H-benzotriazole compound according to any one of claims 1 to 8 in the field of organic synthesis. The use according to claim 9 is characterized in that the use includes use in the fields of medicine, ligands, ultraviolet stabilizers or organic electronic material synthesis.