CN111269098A - Method for synthesizing polyaryl substituted aldehyde compound by polyoxometalate catalytic dehydration coupling reaction - Google Patents
Method for synthesizing polyaryl substituted aldehyde compound by polyoxometalate catalytic dehydration coupling reaction Download PDFInfo
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Abstract
The invention discloses a method for synthesizing polyaryl substituted aldehyde compounds by a polyoxometalate catalytic dehydration coupling reaction, which comprises the following steps: (1) weighing reaction substrates: putting a diphenyl methanol compound and a phenylacetaldehyde compound into a reaction bottle in a ratio of 1: 1-1: 1.5, adding a catalyst polyoxometalate, adding a solvent, stirring magnetons, sealing the reaction bottle, and stirring for reaction; (2) after the reaction is finished, the product is obtained: polyaryl substituted aldehyde compounds. The method has the advantages of high-efficiency, green and cheap catalyst, low catalyst consumption, mild reaction conditions, high yield and water as the only byproduct, and lays a foundation for synthesizing the polyaryl substituted aldehyde compound simply, efficiently and environmentally friendly.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing polyaryl substituted aldehyde compounds through catalytic dehydration coupling reaction of a polyoxometalate.
Background
Aldehyde compounds (i.e. organic compounds containing aldehyde-CHO in molecules) are a very important class of compounds, have various special reactivity, biological activity and pharmaceutical activity, are widely distributed in nature, and not only exist in various natural products and medicines with physiological activity, but also are important components of chemical materials. Particularly, the aryl aldehyde compounds are widely applied to chemical and pharmaceutical industries and play a vital role in the aspects of production, life and the like of human beings.
The key point of the synthesis of the aldehyde compound is to construct a new C-C bond. Although many methods for synthesizing aldehyde compounds have been developed, such as selective oxidation of alcohol or alkane compounds, photocatalytic benzidine and vinyl ether, and reduction of aryl halide aldehyde group catalyzed by Pd/Rh, etc., due to the high reactivity of the aldehyde compounds, the synthesis of polysubstituted aryl aldehyde compounds still faces huge challenges, the selective oxidation of alcohol or alkane is often difficult to control and the number of byproducts is large, and the reduction of aldehyde group catalyzed by photocatalytic coupling synthesis of aldehyde and aryl halide aldehyde group catalyzed by noble metal often faces problems of expensive catalyst, etc.
Disclosure of Invention
The application provides a method for synthesizing polyaryl substituted aldehyde compounds by Polyoxometalates (POMs) catalytic dehydration coupling reaction, which solves the problems of long reaction time, low yield, poor catalytic performance of a catalyst and more byproducts in the existing method.
The purpose of the invention is realized by the following technical scheme:
a method for synthesizing polyaryl substituted aldehyde compounds by a polyoxometalate catalytic dehydration coupling reaction comprises the following steps:
(1) weighing reaction substrates: putting a diphenyl methanol compound and a phenylacetaldehyde compound into a reaction bottle in a ratio of 1: 1-1: 1.5, adding a catalyst polyoxometalate, adding a solvent, stirring magnetons, sealing the reaction bottle, and stirring for reaction;
(2) after the reaction is finished, the product is obtained: polyaryl substituted aldehyde compounds.
Wherein the reaction temperature in the step (1) is 70-120 ℃, and the reaction time is 0-3 h. The dosage of the catalyst is 2-5% of the dosage of the reaction substrate.
The reaction formula of the product polyaryl substituted aldehyde compound is as follows:
the reaction mechanism of the method for synthesizing the polyaryl substituted aldehyde compound by the polyoxometalate catalytic dehydration coupling reaction is as follows:
the reaction substrate phenylacetaldehyde compound 2 undergoes enol tautomerization to become 2', and reacts with the benzhydrol compound 1 to form carbenium ion 4 under the action of a catalyst to form enol 5, and finally the enol 5 generates the polyaryl substituted aldehyde compound 3 through tautomerization.
Aiming at the problems of low yield, more byproducts, expensive catalyst and the like in the existing method, the invention uses the cheap, high-efficiency and green catalyst, namely Keggin type polyoxometalate to catalyze the diphenyl methanol compound and the phenylacetaldehyde compound to synthesize the polysubstituted aryl aldehyde compound, the used catalyst is efficient, green, low-cost, mild in reaction condition and high in yield, and the only byproduct is water. The reaction is synthesized in one step by adopting a one-pot method, the operation is simple, the catalyst is green, environment-friendly and cheap, the pollution to the environment is reduced, and the method is a green and environment-friendly synthesis method and has good industrial production prospect.
Further, the solvent is at least one of the following substances: water, propylene carbonate, hexafluoroisopropanol, N-dimethylformamide, 1, 2-dichloroethane, a dibasic ester mixture, toluene, chlorobenzene, cyclohexane, nitromethane, 1, 4-dioxane, tetrahydrofuran, acetonitrile and the like;
further, the reaction substrate diphenyl carbinol compound is diphenyl carbinol containing substituent on benzene ring, and the substituent R is1And R2Including but not limited to H, methyl (-CH)3) Methoxy (-OCH)3) Fluorine, chlorine, bromine, and the like.
Further, the reaction substrate phenylacetaldehyde compound is phenylacetaldehyde containing substituent groups on a benzene ring, and the substituent groups R comprise H, fluorine, chlorine, bromine and the like without limitation;
furthermore, the usage amount (amount of substances) of the reaction substrate diphenyl carbinol compound and the phenylacetaldehyde compound is 1: 1-1: 1.5.
Further, the catalyst polyoxometalate is Keggin type heteropoly acid with a general formula of [ XM12O40]n-(X ═ P, Si, Ge, As ·, M ═ Mo, W, V), and the amount is 2-5% of the amount of the reaction substrate.
Drawings
FIG. 1 shows a general structural formula (R) of a reaction substrate benzhydrol compound1/R2＝H,CH3,OCH3F, Cl, Br, etc.);
fig. 2 shows a general structural formula of a phenylacetaldehyde-based compound as a reaction substrate (R ═ H, F, Cl, Br, etc.);
FIG. 3 is a reaction scheme.
Detailed Description
The invention will be described in detail with reference to specific examples.
The method for synthesizing the polyaryl substituted aldehyde compound by the catalytic dehydration coupling reaction of the polyoxometalate comprises the following steps:
(1) weighing reaction substrates: putting a benzhydrol compound (the structural general formula is shown in figure 1) and a phenylacetaldehyde compound (the structural general formula is shown in figure 2) into a reaction bottle in a ratio of 1: 1-1: 1.5, adding a catalyst polyoxometalate cluster, adding a solvent, stirring magnetons, sealing the reaction bottle, and stirring for reaction (the reaction schematic diagram is shown in figure 3);
(2) after the reaction is finished, the product is obtained: polyaryl substituted aldehyde compounds.
Wherein the reaction temperature in the step (1) is 70-120 ℃, and the reaction time is 0-3 h. The dosage of the catalyst is 2-5% of the dosage of the reaction substrate.
The reaction formula of the product polyaryl substituted aldehyde compound is as follows:
the reaction mechanism of the method for synthesizing the polyaryl substituted aldehyde compound by the polyoxometalate catalytic dehydration coupling reaction is as follows:
the reaction substrate phenylacetaldehyde compound 2 undergoes enol tautomerization to become 2', and reacts with the benzhydrol compound 1 to form carbenium ion 4 under the action of a catalyst to form enol 5, and finally the enol 5 generates the polyaryl substituted aldehyde compound 3 through tautomerization.
Example 1
0.2mmol of benzhydrol, 0.24mmol of phenylacetaldehyde and 3 mol% of H are weighed out3PW12O40Adding 1mL of nitromethane solvent into a 4mL reaction bottle, adding a stirring magneton, sealing, and reacting for 2 hours at 90 ℃. After the reaction is finished, the target product is obtained by column chromatography separation, and the yield is 91%. The target product is characterized by a nuclear magnetic resonance spectrometer, and the specific result is as follows:
1HNMR(400MHz,CDCl3):δ(ppm)9.69(s,1H),7.37-7.39(m,2H),7.30(t,J＝14.4,7.2Hz,2H),7.08-7.24(m,10H),6.99-7.02(m,1H),4.77(d,J＝12Hz,1H),4.51(d,J＝12Hz,1H)；13CNMR(100.6MHz,CDCl3):δ(ppm)198.85,142.13,141.51,134.41,129.44,128.91,128.89,128.35,128.28,128.13,127.62,126.91,126.34,63.38,52.09。
example 2
A4 mL reaction flask was charged with 1- (2-methylphenyl) -1-phenylmethanol (0.2mmol), phenylacetaldehyde (0.24mmol), and H3PMo12O40(3 mol%) and nitromethane (1 mL). Then reacted at 90 ℃ for 2 hours. After the reaction is finished, the target product is obtained by column chromatography separation, and the yield is 78%. The target product is characterized by a nuclear magnetic resonance spectrometer, and the specific result is as follows:
1H NMR(400MHz,CDCl3):δ(ppm)9.69(s,1H),7.34-7.36(m,2H),7.28-7.29(m,2H),7.15-7.25(m,8H),7.03-7.04(m,1H),6.95(s,1H),5.08(d,J＝12Hz,1H),4.52(d,J＝12Hz,1H),2.26(s,3H)；13C NMR(100.6MHz,CDCl3):δ(ppm)198.97,141.51,139.27,136.09,134.38,130.58,129.20,128.87,128.77,128.58,127.59,127.45,126.80,126.24,125.94,63.76,46.57,20.01。
example 3
A4 mL reaction flask was charged with 1- (4-chlorophenyl) -1-phenylmethanol (0.2mmol), phenylacetaldehyde (0.24mmol), and H3PMo12O40(3 mol%) and nitromethane (1 mL). Then reacted at 90 ℃ for 2 hours. After the reaction is finished, the target product is obtained by column chromatography separation, and the yield is 92%. The target product is characterized by a nuclear magnetic resonance spectrometer, and the specific result is as follows:
1H NMR(400MHz,CDCl3):δ(ppm)9.68(s,1H),7.28-7.35(m,4H),7.17-7.25(m,6H),7.04-7.10(m,3H),6.99-7.01(m,1H),4.75(d,J＝12Hz,1H),4.47(d,J＝12Hz,1H)；13C NMR(100.6MHz,CDCl3):δ(ppm)198.44,141.06,140.88,133.92,132.66,129.48,129.45,129.00,128.47,128.22,127.77,126.56,63.40,51.37。
example 4
In a 4mL reaction flask were added bis (4-chlorophenyl) methanol (0.2mmol), phenylacetaldehyde (0.24mmol), and H3PMo12O40(3 mol%) and nitromethane (1)mL). Then reacted at 90 ℃ for 2 hours. After the reaction is finished, the target product is obtained by column chromatography separation, and the yield is 91%. The target product is characterized by a nuclear magnetic resonance spectrometer, and the specific result is as follows:
1H NMR(400MHz,CDCl3) Delta (ppm)9.68(s,1H),7.26-7.28(m,6H, comprising CDCl)3Peak), 7.18-7.24(m,2H),7.14(d, J ═ 7.2Hz,2H),7.07(d, J ═ 8Hz,2H),6.96(d, J ═ 8Hz,2H),4.73(d, J ═ 12Hz,1H),4.43(d, J ═ 12Hz, 1H);13C NMR(100.6MHz,CDCl3):δ(ppm)197.98,140.39,139.71,133.54,132.88,132.34,129.54,129.46,129.34,129.15,129.11,128.62,127.98,63.28,50.71。
comparative example
The data obtained by screening the catalyst by controlled variables, represented by benzhydrol (0.2mmol) and phenylacetaldehyde (0.24mmol), under otherwise unchanged conditions, are shown in table 1, wherein TfOH ═ trifluoromethanesulfonic acid and p-TSA ═ p-methylbenzenesulfonic acid. Almost no reaction without catalyst, generally higher yield with POMs, and addition of H3PW12O40The catalytic effect is best. Since POMs are more acidic than conventional mineral acids, they act as more efficient proton donors, are better than conventional mineral acids in terms of catalytic activity, and have superior catalytic effects in terms of building C — C bonds.
TABLE 1
| Serial number | Catalyst and process for preparing same | Conversion (%) | Yield (%) |
| 1 | ------- | 9 | 0 |
| 2 | TfOH | 96 | 41 |
| 3 | p-TSA | 45 | 3 |
| 4 | H3PW12O40 | 99 | 68 |
| 5 | H4SiW12O40 | 99 | 83 |
| 6 | H3PMo12O40 | 99 | 91 |
| 7 | H6TeO6 | 9 | 0 |
| 8 | FeCl3 | 14 | 0 |
| 9 | CuCl2 | 22 | 0 |
| 10 | Cu(OTf)2 | 83 | 8 |
| 11 | Sc(OTf)3 | 82 | 15 |
| 12 | Co(CH3COO)2 | 16 | 0 |
| 13 | ZnCl2 | 36 | 1 |
| 14 | Ni(CH3COO)2 | 13 | 0 |
| 15 | AlCl3 | 14 | 0 |
The present invention includes, but is not limited to, the above examples, and any equivalent substitutions or partial modifications made under the principle of the spirit of the present invention are considered to be within the scope of the present invention.
Claims (10)
1. A method for synthesizing polyaryl substituted aldehyde compounds by polyoxometalate catalytic dehydration coupling reaction is characterized by comprising the following steps:
(1) weighing reaction substrates: putting a diphenyl methanol compound and a phenylacetaldehyde compound into a reaction bottle in a ratio of 1: 1-1: 1.5, adding a catalyst polyoxometalate, adding a solvent, stirring magnetons, sealing the reaction bottle, and stirring for reaction;
(2) after the reaction is finished, the product is obtained: polyaryl substituted aldehyde compounds.
2. The method for synthesizing the polyaryl substituted aldehyde compound through the polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the catalyst in the step (1) is Keggin type heteropoly acid with the polyoxometalate as a general formula [ XM ]12O40]n-(X＝P、Si、Ge、As……，M＝Mo、W、V)。
3. The method for synthesizing polyarylation substituted aldehyde compound by polyoxometalate catalyzed dehydration coupling reaction according to claim 1, wherein the solvent added in step (1) is at least one of the following substances: water, propylene carbonate, hexafluoroisopropanol, N-dimethylformamide, 1, 2-dichloroethane, a mixture of dibasic esters, toluene, chlorobenzene, cyclohexane, nitromethane, 1, 4-dioxane, tetrahydrofuran and acetonitrile.
4. The method for synthesizing the polyaryl substituted aldehyde compound through the polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the reaction temperature in the step (1) is 70-120 ℃.
5. The method for synthesizing the polyaryl substituted aldehyde compound through the polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the reaction time in the step (1) is 0-3 hours.
6. The method for synthesizing the polyaryl substituted aldehyde compound through the polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the amount of the catalyst used in the step (1) is 2-5% of the amount of the reaction substrate.
7. The method for synthesizing polyaryl substituted aldehyde compound by polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the benzhydrol compound selected in step (1) has substituents on benzene rings, and the substituents on two benzene rings are R respectively1And R2Including but not limited to H, methyl (-CH)3) Methoxy (-OCH)3) Fluorine, chlorine, bromine and the like, the position of the substituent group is not limited, and the specific structural general formula is as follows:
8. the method for synthesizing the polyaryl substituted aldehyde compound through the polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the benzene ring of the phenylacetaldehyde compound selected in the step (1) contains a substituent, the substituent R includes but is not limited to H, fluorine, chlorine, bromine, etc., the position of the substituent is not limited, and the specific structural formula is as follows:
9. the method for synthesizing the polyaryl substituted aldehyde compound through the polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the dosage ratio of the diaryl methanol to the aryl acetaldehyde selected as the reaction substrate in the step (1) is 1:1.2, and the dosage is the amount of the substance.
10. The method for synthesizing the polyaryl substituted aldehyde compound through the polyoxometalate catalytic dehydration coupling reaction according to claim 1, wherein the aryl group in the reaction product polyaryl substituted aldehyde compound in the step (2) is a substituted phenyl group, and the specific structural formula is as follows:
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| CN113004236A (en) * | 2021-02-04 | 2021-06-22 | 东华理工大学 | Method for synthesizing 3-methylene benzofuran-1 (3H) -ketone compound |
| CN114345370A (en) * | 2021-12-03 | 2022-04-15 | 陕西师范大学 | Method for reducing and cross-coupling aromatic olefin and halogenated hydrocarbon through photocatalysis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113004236A (en) * | 2021-02-04 | 2021-06-22 | 东华理工大学 | Method for synthesizing 3-methylene benzofuran-1 (3H) -ketone compound |
| CN113004236B (en) * | 2021-02-04 | 2023-05-19 | 东华理工大学 | Method for synthesizing 3-methylenebenzofuran-1 (3H) -one compound |
| CN114345370A (en) * | 2021-12-03 | 2022-04-15 | 陕西师范大学 | Method for reducing and cross-coupling aromatic olefin and halogenated hydrocarbon through photocatalysis |
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