CN114933512A - Method for synthesizing ester compound under photocatalysis condition - Google Patents

Method for synthesizing ester compound under photocatalysis condition Download PDF

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CN114933512A
CN114933512A CN202210576474.5A CN202210576474A CN114933512A CN 114933512 A CN114933512 A CN 114933512A CN 202210576474 A CN202210576474 A CN 202210576474A CN 114933512 A CN114933512 A CN 114933512A
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李盼
赵静静
曹梦婷
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Henan University
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Abstract

The invention provides a method for synthesizing ester compounds under the photocatalysis condition, which takes carboxylic acid and diazo ester as raw materials, adds solvent, and reacts under the action of illumination and heating condition to synthesize the ester compounds. Under the illumination condition, the diazo ester can react with alkyl carboxylic acid and aryl substituted carboxylic acid to obtain an ester compound; the reaction of the invention does not need to add any photosensitizer or catalyst, and does not need to react under inert gas, and the invention has simple operation and high yield.

Description

Method for synthesizing ester compound under photocatalysis condition
Technical Field
The invention relates to the technical field of compound preparation, in particular to a method for synthesizing an ester compound under a photocatalytic condition.
Background
In 2021, the group of the handsome at the university of Anhui reported the synthesis of hydroxyimino ether (org. Lett.2021,23, 6951-one 6955) by the functionalization of oxime with diazo ester O-H under blue light irradiation, and in the experiment the authors found that when the reaction was carried out using tetrahydrofuran as solvent, the target compound was obtained by cleavage of the C-H bond, and the diazo ester thereof only represented aryl diazo ester. The Juroughua project group at the university of Hunan reports that copper catalyzes the double-carbon C-O bond of cyclic ether, carboxylic acid, NaI and TMSCF3 to generate iodoalkyl ester (Org.Lett.2022,24, 2826-one 2831), and reports that ester compounds are obtained by C-H bond activation and tetrahydrofuran ring opening under the condition of metal catalysis, and the reaction needs metal catalysts and high temperature and has harsh reaction conditions. Therefore, on the basis, a new method for synthesizing ester compounds by diazo ester, tetrahydrofuran and carboxylic acid under the induction of visible light is developed, and the problems that the diazo ester is only limited to aryl diazo ester and the reaction conditions are harsh are solved.
Disclosure of Invention
The invention provides a method for three-component reaction of diazo ester, tetrahydrofuran and carboxylic acid under the photocatalysis condition, which can lead the diazo ester to react with aryl substituted carboxylic acid and non-activated alkyl carboxylic acid under the induction of visible light so as to obtain various ester compounds.
The invention adopts the following technical scheme:
a method for synthesizing ester compounds under photocatalytic conditions comprises the following steps:
taking carboxylic acid shown in a formula I and diazo ester shown in a formula II as raw materials, adding a solvent, and reacting under the action of illumination and heating to synthesize an ester compound shown in a formula III; the synthetic route is as follows:
Figure BDA0003662356120000011
wherein: r1 is selected from alkyl, aryl or substituted aryl; r2 is selected from alkyl or benzyl.
Further, the molar ratio of the carboxylic acid shown in the formula I to the diazo ester shown in the formula II is 1: 2.
Further, the ratio of the carboxylic acid represented by the formula I to the solvent is 1 mmol: 5 mL.
Further, the solvent is one or more of tetrahydrofuran, acetonitrile, methanol, toluene, chloroform, ethyl acetate and N, N-dimethylformamide. Preferably, the solvent is tetrahydrofuran.
Further, the illumination is blue light.
Further, the light irradiation is blue light with the wavelength ranging from 405nm to 470 nm. Preferably, the illumination is 455nm blue light.
Further, the temperature is 20-80 ℃. Preferably, the temperature is 60 ℃.
According to the method, diazo ester generates carbene under the action of light, the carbene is captured to obtain a cyclic oxonium ion intermediate under the action of a tetrahydrofuran solvent, then the oxonium ion intermediate is subjected to protonation by removing carboxylic acid protons, and finally carboxylate radical attacks the protonated oxonium ion intermediate to carry out ring opening to obtain a three-component reaction product.
Compared with the prior art, the invention has the following technical effects:
under the illumination condition, the diazo ester can react with alkyl carboxylic acid and aryl substituted carboxylic acid to obtain an ester compound; the reaction of the invention does not need to add any photosensitizer, catalyst or inert gas, and has the advantages of simple operation, high yield, wide substrate range, excellent functional group tolerance and simple condition, and gram-scale preparation can be carried out, thereby further proving the synthetic potential of the method.
Drawings
FIG. 1 is a NMR chart of butyl 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoate in example 1 of the present invention;
FIG. 2 is a NMR carbon spectrum of butyl 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoate used in example 1 of the present invention;
FIG. 3 is a NMR chart of butyl 4- (2- (allyloxy) -2-oxoethoxy) -4-methylbenzoate in example 2 of the present invention;
FIG. 4 is a NMR carbon spectrum of butyl 4- (2- (allyloxy) -2-oxoethoxy) 4-methylbenzoate in example 2 of the present invention;
FIG. 5 is a NMR spectrum of butyl 4- (2-oxo-2- (pyrrolidin-1-yl) ethoxy) -4-methylbenzoate in example 3 of the present invention;
FIG. 6 is a NMR carbon spectrum of butyl 4- (2-oxo-2- (pyrrolidin-1-yl) ethoxy) -4-methylbenzoate in example 3 of the present invention;
FIG. 7 is a NMR chart of butyl 4- (2-ethoxy-2-oxyethoxy) -2-hydroxybenzoate in example 4 of the present invention.
FIG. 8 is a NMR carbon spectrum of butyl 4- (2-ethoxy-2-oxoethoxy) -2-hydroxybenzoate in example 4 of the present invention.
FIG. 9 shows the NMR spectrum of butyl 4- (2-ethoxy-2-oxyethoxy) -2-iodobenzoate in example 5 of the present invention.
FIG. 10 is the NMR carbon spectrum of butyl 4- (2-ethoxy-2-oxyethoxy) -2-iodobenzoate in example 5 of the present invention.
FIG. 11 is a NMR chart of butyl 4- (2-ethoxy-2-oxoethoxy) -4-bromobenzoate in example 6 of the present invention.
FIG. 12 is a NMR carbon spectrum of butyl 4- (2-ethoxy-2-oxoethoxy) -4-bromobenzoate of example 6 of the present invention.
Detailed Description
The invention is further described with reference to the following figures and detailed description. The following examples are intended to illustrate the invention, but are not intended to limit the scope of the invention. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art. The test methods in the following examples are all conventional methods unless otherwise specified.
Example 1
Take quartz reaction tube, add one of magnetic stirrers to it, then add 0.4mmol of p-toluic acid, 2mL of Tetrahydrofuran (THF), and finally add 0.8mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The product was 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoic acid butyl ester. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 93% yield. The reaction equation is as follows:
Figure BDA0003662356120000031
the NMR spectrum of butyl 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoate is characterized as follows: 1 H NMR(300MHz,CDCl 3 )δ7.91(d,J＝8.2Hz,2H),7.22(d,J＝8.0Hz,2H),4.33(t,J＝6.2Hz,2H),4.21(q,J＝7.2Hz,2H),4.07(s,2H)3.59(t,J＝6.1Hz,2H),2.40(s,3H),1.94–1.72(m,4H),1.28(t,J＝7.1Hz,3H).
the NMR spectrum of butyl 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoate is characterized as follows: 13 C NMR(75MHz,CDCl 3 )δ170.4,166.6,143.4,129.5,129.0,127.6,71.2,68.3,64.4,60.8,26.2,25.4,21.6,14.2。
example 2
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of p-toluic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 0.8mmol of 2-diazoacetic acid allyl ester.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light to react for 12h, and the reaction is finished. The product was butyl 4- (2- (allyloxy) -2-oxoethoxy) -4-methylbenzoate. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 53% yield. The reaction equation is as follows:
Figure BDA0003662356120000041
the NMR spectrum of butyl 4- (2- (allyloxy) -2-oxoethoxy) -4-methylbenzoate is characterized as follows: 1 H NMR(300MHz,CDCl 3 )δ7.92(d,J＝8.2Hz,2H),7.23(d,J＝8.0Hz,2H),5.92(ddt,J＝16.5,10.2,5.8Hz,1H),5.38–5.22(m,2H),4.65(d,J＝5.9Hz,2H),4.33(t,J＝6.2Hz,2H),4.11(s,2H),3.60(t,J＝6.1Hz,2H),2.40(s,3H),1.95–1.72(m,4H).
the NMR spectrum of butyl 4- (2- (allyloxy) -2-oxoethoxy) -4-methylbenzoate is characterized as follows: 13 C NMR(75MHz,CDCl 3 )δ170.1,166.6,143.5,131.6,129.5,129.0,127.6,118.8,71.2,68.2,65.4,64.4,26.2,25.4,21.3。
example 3
A quartz reaction tube was taken, to which one magnetic stirrer was added, then 0.4mmol of p-toluic acid, 2mL of Tetrahydrofuran (THF), and finally 0.8mmol of 2-diazo-1- (pyrrolidin-1-yl) ethan-1-one were added.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The product was 4- (2-oxo-2- (pyrrolidin-1-yl) ethoxy) -4-methylbenzoic acid butyl ester. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 69% yield. The reaction equation is as follows:
Figure BDA0003662356120000042
the NMR spectrum of butyl 4- (2-oxo-2- (pyrrolidin-1-yl) ethoxy) -4-methylbenzoate is characterized as follows: 1 H NMR(300MHz,CDCl 3 )δ7.91(d,J＝8.2Hz,2H),7.22(d,J＝8.0Hz,2H),4.32(t,J＝6.2Hz,2H),4.08(s,2H),3.59(t,J＝6.1Hz,2H),3.46(s,4H),2.40(s,3H),1.91-1.75(m,8H).
the NMR spectrum of butyl 4- (2-oxo-2- (pyrrolidin-1-yl) ethoxy) -4-methylbenzoate is characterized as follows: 13 C NMR(75MHz,CDCl 3 )δ167.8,166.5,143.3,129.4,128.9,127.5,70.8,70.4,64.4,45.7,45.5,26.1,26.1,25.4,23.7,21.5。
example 4
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of o-hydroxybenzoic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The product was butyl 4- (2-ethoxy-2-oxoethoxy) -2-hydroxybenzoate. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 98% yield. The reaction equation is as follows:
Figure BDA0003662356120000051
the NMR spectrum of butyl 4- (2-ethoxy-2-oxyethoxy) -2-hydroxybenzoate was characterized as follows: 1 H NMR(300MHz,CDCl 3 )δ10.81(s,1H),7.82(dd,J＝8.0,1.8Hz,1H),7.43(ddd,J＝8.7,7.2,1.8Hz,1H),6.96(dd,J＝8.4,1.1Hz,1H),6.86(ddd,J＝8.2,7.2,1.1Hz,1H),4.38(t,J＝6.4Hz,2H),4.20(q,J＝7.1Hz,2H),4.06(s,2H),3.59(t,J＝6.1Hz,2H),1.96–1.71(m,4H),1.27(t,J＝7.1Hz,3H).
the NMR spectrum of butyl 4- (2-ethoxy-2-oxyethoxy) -2-hydroxybenzoate was characterized as follows: 13 C NMR(75MHz,CDCl 3 )δ170.3,170.0,161.5,135.5,129.7,119.0,117.4,112.4,70.9,68.2,64.9,60.7,26.0,25.2,14.1。
example 5
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of 2-iodobenzoic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The product was 4- (2-ethoxy-2-oxoethoxy) -2-iodobenzoic acid butyl ester. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 90% yield. The reaction equation is as follows:
Figure BDA0003662356120000061
the NMR spectrum of butyl 4- (2-ethoxy-2-oxyethoxy) -2-iodobenzoate was characterized as follows: 1 H NMR(300MHz,CDCl 3 )δ7.96(dd,J＝8.0,1.1Hz,1H),7.77(dd,J＝7.8,1.7Hz,1H),7.38(td,J＝7.6,1.2Hz,1H),7.12(td,J＝7.7,1.7Hz,1H),4.36(t,J＝6.3Hz,2H),4.20(q,J＝7.1Hz,2H),4.05(s,2H),3.58(t,J＝6.1Hz,2H),1.97–1.72(m,4H),1.26(t,J＝7.1Hz,3H).
the NMR spectrum of butyl 4- (2-ethoxy-2-oxyethoxy) -2-iodobenzoate was characterized as follows: 13 C NMR(75MHz,CDCl 3 )δ170.3,166.4,141.0,135.1,132.4,130.7,127.7,93.8,70.9,68.1,65.2,60.6,26.1,25.1,14.1。
example 6
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by 0.4mmol of 4-bromobenzoic acid, 2mL of Tetrahydrofuran (THF), and finally 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The product was 4- (2-ethoxy-2-oxoethoxy) -4-bromobenzoic acid butyl ester. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 98% yield. The reaction equation is as follows:
Figure BDA0003662356120000062
NMR spectra of 4- (2-ethoxy-2-oxyethoxy) -4-bromobenzoate were characterized as follows: 1 H NMR(300MHz,CDCl 3 )δ7.89(d,J＝8.6Hz,2H),7.56(d,J＝8.5Hz,2H),4.35(t,J＝6.3Hz,2H),4.21(q,J＝7.1Hz,2H),4.07(s,2H),3.59(t,J＝6.1Hz,2H),1.94–1.70(m,4H),1.28(t,J＝7.1Hz,3H).
the NMR spectrum of 4- (2-ethoxy-2-oxyethoxy) -4-bromobenzoate was characterized as follows: 13 C NMR(75MHz,CDCl 3 )δ170.3,165.7,131.5,131.0,129.1,127.8,71.0,68.2,64.8,60.7,26.1,25.3,14.1。
example 7
Take quartz reaction tube, add one of magnetic stirrers to it, then add 0.4mmol of p-toluic acid, 2mL Tetrahydrofuran (THF), and finally add 0.8mmol of cyclohexyl 2-diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light to react for 12h, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 81% yield. The reaction equation is as follows:
Figure BDA0003662356120000071
example 8
Take quartz reaction tube, add one of magnetic stirrers to it, then add 0.4mmol of p-toluic acid, 2mL of Tetrahydrofuran (THF), and finally add 0.8mmol of benzyl 2-diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography in 76% yield. The reaction equation is as follows:
Figure BDA0003662356120000072
example 9
Take quartz reaction tube, add one of magnetic stirrers to it, then add 0.4mmol of p-toluic acid, 2mL Tetrahydrofuran (THF), and finally add 0.8mmol of (E) -3, 7-dimethyl-2, 6-dien-1-yl 2-diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 95% yield. The reaction equation is as follows:
Figure BDA0003662356120000073
example 10
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of p-toluic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 0.8mmol of 3-phenylpropyl 2-diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 73% yield. The reaction equation is as follows:
Figure BDA0003662356120000081
example 11
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of p-toluic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 0.8mmol of ethyl 2- (thien-2-yl) -2-diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 97% yield. The reaction equation is as follows:
Figure BDA0003662356120000082
example 12
Take quartz reaction tube, add one of magnetic stirrers to it, then add 0.4mmol of p-toluic acid, 2mL Tetrahydrofuran (THF), and finally add 0.8mmol of cinnamyl 2-diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 64% yield. The reaction equation is as follows:
Figure BDA0003662356120000083
example 13
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of 2-naphthoic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography in 96% yield. The reaction equation is as follows:
Figure BDA0003662356120000084
example 14
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of 2-pyridinecarboxylic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography in 92% yield. The reaction equation is as follows:
Figure BDA0003662356120000091
example 15
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of nicotinic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 98% yield. The reaction equation is as follows:
Figure BDA0003662356120000092
example 16
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of 4-cyanobenzoic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light for reaction for 12 hours, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 97% yield. The reaction equation is as follows:
Figure BDA0003662356120000093
preparation of example 17
A quartz reaction tube was taken, and one magnetic stirrer was added thereto, followed by addition of 0.4mmol of 4-cyanobenzoic acid, 2mL of Tetrahydrofuran (THF), and finally addition of 1.2mmol of ethyl diazoacetate.
Then the mixture is heated to 60 ℃ under the light of 455nm ultraviolet light to react for 12h, and the reaction is finished. The final product was checked by TLC and finally isolated by column chromatography to give the final product in 85% yield. The reaction equation is as follows:
Figure BDA0003662356120000094
example 18 reaction condition optimization
1. Solvent optimization
The solvent was screened according to the reaction substrate and reaction conditions of example 1, and the remaining conditions were the same except that the solvent was different. The reaction equation is as follows:
Figure BDA0003662356120000101
the yields of the product under different solvent conditions are shown in table 1:
TABLE 1 yield of butyl 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoate under different solvent conditions
Serial number Light source Temperature of Solvent(s) Yield of
1 455nm 60℃ Tetrahydrofuran (THF) 93％
2 455nm 60℃ Acetonitrile 51％
3 455nm 60℃ Methanol 46％
4 455nm 60℃ Toluene 35％
5 455nm 60℃ Trichloromethane 42％
6 455nm 60℃ Ethyl acetate 28％
7 455nm 60℃ N, N-dimethylformamide 26％
The above results show that the product can be obtained under different solvent conditions, and tetrahydrofuran is the best solvent for the substrates of p-toluic acid and ethyl diazoacetate.
2. Optimization of light sources
The solvent was screened according to the reaction substrate and reaction conditions of example 1, and all the conditions were the same except that the wavelength of the light source was different. The reaction equation is as follows:
Figure BDA0003662356120000102
the yields of the product under different wavelengths of blue light are shown in table 2:
TABLE 2 yield of butyl 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoate under blue light of different wavelengths
Figure BDA0003662356120000103
Figure BDA0003662356120000111
The results show that the product can be obtained under the condition of blue light with different wavelengths, and the blue light with the wavelength of 455nm is the best light source for the substrates of methylbenzoic acid and ethyl diazoacetate.
3. Optimization of temperature
The solvent was screened according to the reaction substrate and reaction conditions of example 1, and the remaining conditions were the same, with only a temperature difference. The reaction equation is as follows:
Figure BDA0003662356120000112
the yields of the product under different temperature conditions are shown in table 3:
TABLE 3 yield of butyl 4- (2-ethoxy-2-oxoethoxy) -4-methylbenzoate under different temperature conditions
Serial number Light source Temperature of Solvent(s) Yield of
1 455nm 20℃ Tetrahydrofuran (THF) 67％
2 455nm 30℃ Tetrahydrofuran (THF) 70％
3 455nm 40℃ Tetrahydrofuran (THF) 73％
4 455nm 50℃ Tetrahydrofuran (THF) 82％
5 455nm 60℃ Tetrahydrofuran (THF) 93％
6 455nm 70℃ Tetrahydrofuran (THF) 80％
7 455nm 80℃ Tetrahydrofuran (THF) 76％
The results show that under different temperature conditions, the product can be obtained, and the temperature of 60 ℃ is the optimal temperature for the substrates of p-toluic acid and ethyl diazoacetate.
The above-mentioned embodiments are only preferred embodiments of the present invention, and are not intended to limit the scope of the present invention, and it is obvious to those skilled in the art that other embodiments can be easily made by replacing or changing the technical contents disclosed in the present specification, and therefore, the changes and modifications made by the principles and process conditions of the present invention should be included in the claims of the present invention.

Claims (8)

1. A method for synthesizing ester compounds under the condition of photocatalysis is characterized by comprising the following steps:
taking carboxylic acid shown in a formula I and diazo ester shown in a formula II as raw materials, adding a solvent, and reacting under the action of illumination and heating to synthesize an ester compound shown in a formula III; the reaction equation is as follows:
Figure FDA0003662356110000011
wherein: r is 1 Selected from alkyl, aryl or substituted aryl; r is 2 Selected from alkyl or benzyl.
2. The method for synthesizing the ester compound under the photocatalytic condition according to claim 1, wherein the molar ratio of the carboxylic acid shown in the formula I to the diazo ester shown in the formula II is 1 (2-3).
3. The method for synthesizing ester compounds under the photocatalytic condition according to claim 1, wherein the ratio of the carboxylic acid represented by the formula I to the solvent is 1 mmol: 5 mL.
4. The method for synthesizing ester compounds under photocatalytic conditions according to claim 1, wherein the solvent is one or more of tetrahydrofuran, acetonitrile, methanol, toluene, chloroform, ethyl acetate, and N, N-dimethylformamide.
5. The method of claim 1, wherein the light is blue light.
6. The method for synthesizing ester compounds under photocatalytic conditions as claimed in claim 1, wherein the illumination is blue light with a wavelength ranging from 405nm to 470 nm.
7. The method for synthesizing ester compounds under the photocatalytic condition according to claim 1, wherein the temperature is 20-80 ℃.
8. The method for synthesizing ester compounds under the photocatalytic condition as recited in claim 1, wherein the reaction time is 12 hours.
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