CN111533717B - Method for synthesizing 3-arylmethylbenzo [ b ] furan compound under blue light excitation - Google Patents
Method for synthesizing 3-arylmethylbenzo [ b ] furan compound under blue light excitation Download PDFInfo
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Abstract
The invention provides a method for synthesizing a 3-arylmethylbenzofuran compound under blue light excitation, belonging to the technical field of organic synthesis. The invention uses photocatalyst to catalyze decarboxylation cyclization of o-alkynyl phenoxyacetic acid to prepare the 3-arylmethyl benzo [ b ] furan compound. Compared with the existing method for synthesizing the compound, the method has the following advantages: 1) The whole reaction process does not need metal catalysts and dangerous peroxide compounds, so that the reaction safety is high, and the cost is low; 2) The whole reaction process can be finished at room temperature without heating, and the reaction condition is mild; 3) Strong acid and strong alkali are not needed in the whole reaction process; 4) The by-product of the reaction is only carbon dioxide, which meets the requirement of green chemical development.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing a 3-arylmethylbenzofuran compound under the excitation of blue light.
Background
3-arylmethylbenzofuran compounds widely exist in nature, a plurality of natural products, drug intermediates, bioactive molecules and organic materials contain 3-arylmethylbenzofuran compound structural units, and the synthesis of the compounds is a hotspot of organic synthesis research. The research on the synthesis of 3-arylmethylbenzo [ b ] furan compounds is also a research focus of attention of chemists, and the synthesis method comprises the classical condensation reaction catalyzed by Lewis acid, the oxidative cyclization reaction of ortho-disubstituted aryl catalyzed by transition metal, the C-H bond activation reaction catalyzed by transition metal and the like. However, these processes typically yield benzo [ b ] furans disubstituted 2,3-positions. Moreover, from literature reports, the catalytic systems for the synthesis of 3-arylmethylbenzo [ b ] furan compounds have focused mainly on transition metal catalysis. An Ohmura subject group (chem.Eur.J.2016, 22,10415) utilizes iridium to catalyze a tandem reaction of C-H bond addition in an o-methoxy aryne molecule to obtain a 3-aryl substituted benzo [ b ] furan compound; wang Wei and the like (Chin.J.org.chem.2019, 39, 456-462) utilize a palladium catalytic system to catalyze the intramolecular Heck reaction of o-bromoaryl phenyl allyl ether to synthesize the 3-aryl substituted benzo [ b ] furan compound. In the methods, reaction catalysts belong to noble metal catalysts, the price is high, and the reaction conditions are harsh, so that the popularization and application of the existing method for synthesizing the 3-arylmethylbenzofuran compound in industrial production are limited.
Therefore, how to synthesize the 3-arylmethyl benzo [ b ] furan compound in a green way under the condition of no metal has important significance.
Disclosure of Invention
The invention aims to provide a method for synthesizing a 3-arylmethylbenzofuran compound under blue light excitation, which does not need a metal catalyst or heating, has mild reaction conditions, and is green and environment-friendly in synthesis process.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a method for synthesizing a 3-arylmethylbenzofuran compound under the excitation of blue light, which comprises the following steps:
mixing an o-alkynyl phenoxyacetic acid compound, a photocatalyst, a free radical regulator, alkali and a reaction solvent, and carrying out cyclization reaction under the condition of blue light irradiation to obtain a 3-arylmethylbenzofuran compound;
the temperature of the cyclization reaction is room temperature; the alkali is diisopropylethylamine, pyridine or triethylamine;
the o-alkynyl phenoxyacetic acid compound has a structure shown in a formula I:
the 3-arylmethylbenzo [ b ] furan compound has a structure shown in a formula II:
in the formulas I and II, R is independently-H, -Me, -OMe, -F or-Cl; r 1 independently-H, -Me, -OMe, -F, -Cl or-CN.
Preferably, the photocatalyst comprises 9-mesityl-10-phenylacridine tetrafluoroborate, ir (dtbbpy) (ppy) 2 ]PF 6 Or IrdF (CF) 3 )ppy] 2 (dtbbpy)PF 6 。
Preferably, the free radical regulator comprises (PhS) 2 PhSH or azobisisobutyronitrile.
Preferably, the reaction solvent comprises trifluoroethanol, acetonitrile, methanol or dimethyl sulfoxide.
Preferably, the molar ratio of the o-alkynyl phenoxyacetic acid compound to the photocatalyst to the free radical regulator to the alkali is 1 (0.05-0.2) to (0.15-0.4) to (0.5-2).
Preferably, the dosage ratio of the o-alkynyl phenoxyacetic acid compound to the reaction solvent is 0.2mmol (2-10) mL.
Preferably, the power of the blue light irradiation is 20-30W, and the blue light irradiation is realized by blue LED illumination.
Preferably, the cyclization reaction is carried out in a helium atmosphere, and the time of the cyclization reaction is 24-36 h.
Preferably, after the cyclization reaction is completed, the method further comprises: and (3) sequentially carrying out reduced pressure concentration and silica gel column chromatography separation on the mixed solution obtained by the reaction to obtain the 3-arylmethylbenzofuran compound.
The invention provides a method for synthesizing a 3-arylmethylbenzofuran compound under the excitation of blue light, which comprises the following steps: mixing an o-alkynyl phenoxyacetic acid compound, a photocatalyst, a free radical regulator, alkali and a reaction solvent, and carrying out cyclization reaction under the condition of blue light irradiation to obtain a 3-arylmethylbenzofuran compound; the temperature of the cyclization reaction is room temperature; the base is diisopropylethylamine, pyridine or triethylamine.
Under the condition of blue light irradiation, the photocatalyst absorbs blue light, and promotes the photocatalyst to catalyze the decarboxylation and cyclization of the o-alkynyl phenoxyacetic acid, so that the 3-arylmethylbenzofuran compound is prepared. Compared with the existing method for synthesizing the compound, the method has the following advantages: 1) The whole reaction process does not need a metal catalyst and a dangerous peroxide compound, so that the reaction safety is high, and the cost is low; 2) The whole reaction process can be finished at room temperature without heating, and the reaction condition is mild; 3) Strong acid and strong alkali are not needed in the whole reaction process; 4) The by-product of the reaction is only carbon dioxide, which meets the requirement of green chemical development.
Drawings
FIG. 1 is a hydrogen spectrum of the product prepared in example 1;
FIG. 2 is a carbon spectrum of the product prepared in example 1;
FIG. 3 is a hydrogen spectrum of the product prepared in example 2;
FIG. 4 is a carbon spectrum of the product prepared in example 2;
FIG. 5 is a hydrogen spectrum of the product prepared in example 3;
FIG. 6 is a carbon spectrum of the product prepared in example 3.
Detailed Description
The invention provides a method for synthesizing a 3-arylmethylbenzofuran compound under the excitation of blue light, which comprises the following steps:
mixing an o-alkynyl phenoxyacetic acid compound, a photocatalyst, a free radical regulator, alkali and a reaction solvent, and carrying out cyclization reaction under the condition of blue light irradiation to obtain a 3-arylmethylbenzofuran compound;
the temperature of the cyclization reaction is room temperature; the alkali is diisopropylethylamine, pyridine or triethylamine;
the o-alkynyl phenoxyacetic acid compound has a structure shown in a formula I:
the 3-arylmethylbenzo [ b ] furan compound has a structure shown in formula II:
in the formulas I and II, R is independently-H, -Me, -OMe, -F or-Cl; r 1 independently-H, -Me, -OMe, -F, -Cl or-CN.
In the present invention, unless otherwise specified, all the starting materials required for the preparation are commercially available products well known to those skilled in the art.
The invention mixes the o-alkynyl phenoxyacetic acid compound, the photocatalyst, the free radical regulator, the alkali and the reaction solvent. In the invention, the o-alkynyl phenoxyacetic acid compound has a structure shown in a formula I:
wherein R is independently-H, -Me, -OMe, -F or-Cl; r 1 independently-H, -Me, -OMe, -F, -Cl or-CN. In the invention, the o-alkynyl phenoxyacetic acid compound specifically comprises 2- (2- (2-phenylacetylene) phenoxy) -acetic acid, 2- (2- (2-p-methylphenylacetylene) phenoxy) -acetic acid or 2- (2- (2-p-methoxyphenylacetylene) phenoxy) -acetic acid.
In the present invention, the photocatalyst preferably comprises 9-mesityl-10-phenylacridine tetrafluoroborate, ir (dtbbpy) (ppy) 2 ]PF 6 (CASNO. 676525-77-2) or IrdF (CF) 3 )ppy] 2 (dtbb py)PF 6 (CASNO.870987-63-6). In the present invention, the purity of the photocatalyst is preferably 99.99% or more.
In the present invention, the radical regulator preferably comprises (PhS) 2 PhSH or azobisisobutyronitrile. The invention uses the free radical regulator as an electron acceptor of cyclization reaction to promote the cyclization reaction.
In the present invention, the base is diisopropylethylamine, pyridine or triethylamine; the invention uses alkali to abstract the proton of acid.
In the present invention, the reaction solvent preferably includes trifluoroethanol, acetonitrile, methanol or dimethyl sulfoxide.
In the invention, the molar ratio of the o-alkynyl phenoxyacetic acid compound, the photocatalyst, the free radical regulator and the alkali is preferably 1 (0.05-0.2): (0.15-0.4): 0.5-2), more preferably 1 (0.08-0.15): 0.2-0.35): 1.0-1.8, and still more preferably 1 (0.1-0.12): 0.25-0.3): 1.2-1.5.
In the invention, the dosage ratio of the o-alkynyl phenoxyacetic acid compound to the reaction solvent is preferably 0.2mmol (2-10) mL, and more preferably 0.2mmol (5-8) mL.
In the invention, the o-alkynyl phenoxyacetic acid compound, the photocatalyst, the free radical regulator, the base and the reaction solvent are all commercial products from sources well known in the field, and the purity of the raw materials is preferably more than or equal to 99.99%; the reaction solvent is preferably a chromatographically pure reagent.
The mixing process is not particularly limited in the present invention, and the raw materials can be uniformly mixed according to a process well known in the art.
After the mixing is completed, the obtained mixture is subjected to cyclization reaction under the condition of blue light irradiation, so that the 3-arylmethylbenzo [ b ] furan compound is obtained. In the present invention, the power of the blue light irradiation is preferably 20 to 30W, more preferably 22 to 26W, and further preferably 23 to 25W, and the blue light irradiation is preferably performed by blue LED irradiation. The invention provides reaction energy by blue light irradiation, promotes decarboxylation and cyclization of o-alkynyl phenoxyacetic acid, and generates a 3-arylmethylbenzo [ b ] furan compound.
In the present invention, the cyclization reaction is preferably carried out under a helium atmosphere, and the present invention prevents air from entering the reaction by the helium atmosphere; in the present invention, the temperature of the cyclization reaction is room temperature, and the time of the cyclization reaction is preferably 24 to 36 hours, more preferably 28 to 32 hours, and still more preferably 30 hours. In the present invention, the cyclization reaction is preferably carried out under stirring conditions, and the stirring rate is not particularly limited in the present invention, and the reaction can be sufficiently carried out. In the present invention, the cyclization reaction is preferably carried out in a Schlenk closed tube reactor.
In the present invention, the process of the cyclization reaction is as follows:
according to the invention, after the cyclization reaction is completely detected by TLC, the mixed solution obtained by the reaction is subjected to reduced pressure concentration and silica gel column chromatography separation in sequence to obtain the 3-arylmethylbenzofuran compound. The process of the present invention for the concentration under reduced pressure and the separation by silica gel column chromatography is not particularly limited, and may be performed according to a process well known in the art. In the embodiment of the invention, the eluent separated by the silica gel column chromatography is specifically a mixed solution of n-hexane and ethyl acetate, and the volume ratio of the n-hexane and the ethyl acetate is not particularly limited and can be adjusted according to actual requirements.
In the present invention, the 3-arylmethylbenzo [ b ] furan compound is preferably:
the technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
2- (2- (2-phenylacetylene) phenoxy) acetic acid (0.2 mmol, purity 99.99%) and a photocatalyst, 9-mesityl-10-phenylacridine tetrafluoroborate (0.01 mmol, purity 99.99%) were added to a Schlenk closed-loop reactor%), trifluoroethanol (2 mL, chromatographically pure), (PhS) 2 (0.03 mmol, purity 99.99%) and diisopropylethylamine (0.1 mmol, purity 99.99%), stirring and reacting for 24 hours at room temperature under 30W blue LED illumination and helium atmosphere, detecting complete reaction by TLC, concentrating the mixed solution after reaction under reduced pressure to obtain a residue, and separating the residue by silica gel column chromatography, wherein the eluent of the silica gel column chromatography is a mixed solution of n-hexane and ethyl acetate (the volume ratio of n-hexane to ethyl acetate is 100)]And (3) furan.
The nuclear magnetic characterization of the product prepared in this example is shown in fig. 1-2, and the nuclear magnetic data is: 1 H NMR(400MHz,CDCl 3 )δ:7.45(d,J＝8.0Hz,1H),7.40(d,J＝8.0Hz,1H),7.36(s,1H),7.30-7.17(m,6H),7.16-7.12(m,1H),4.02(s,2H)； 13 CNMR(100MHz,CDCl 3 )δ:155.4,142.1,139.1,128.6,128.4,128.0,126.4,124.1,122.2,120.0,119.6,111.3,29.9。
from the nuclear magnetic data, the 3-arylmethylbenzo [ b ] furan compound having the target structure was prepared in this example.
Example 2
To a Schlenk closed tube reactor were added 2- (2- (2-p-methylphenylacetylene) phenoxy) acetic acid (0.2 mmol, purity 99.99%), 9-mesityl-10-phenylacridine tetrafluoroborate (0.03 mmol, purity 99.99%), trifluoroethanol (3 mL, chromatographically pure), (PhS) 2 (0.05 mmol, purity 99.99%) and diisopropylethylamine (0.2 mmol, purity 99.99%), stirring and reacting for 24 hours at room temperature under 30W of blue LED illumination and helium atmosphere, detecting complete reaction by TLC, concentrating the mixed solution after reaction under reduced pressure to obtain residue, and separating the residue by silica gel column chromatography, wherein the eluent of the silica gel column chromatography is mixed solution of n-hexane and ethyl acetate (the volume ratio of n-hexane to ethyl acetate is 100)]Furan p-tolylmethane.
To the bookThe products prepared in the examples were subjected to nuclear magnetic characterization, and the results are shown in fig. 3-4, and the nuclear magnetic data are as follows: 1 H NMR(400MHz,CDCl 3 )δ:7.45(d,J＝8.4Hz,1H),7.41-7.37(m,1H),7.30-7.27(m,1H),7.20(d,J＝8.0Hz,2H),7.16-7.13(m,1H),7.10(d,J＝8.0Hz,2H),4.01(s,2H),2.31(s,3H)； 13 CNMR(100MHz,CDCl 3 )δ:155.6,142.0,136.1,135.7,129.2,128.6,128.0,124.2,122.2,120.0,119.8,111.4,29.6,21.1。
from the nuclear magnetic data, the 3-arylmethylbenzo [ b ] furan compound having the target structure was prepared in this example.
Example 3
To a Schlenk closed tube reactor was added 2- (2- (2-p-methoxyphenylacetylene) phenoxy) -acetic acid (0.2 mmol, purity 99.99%), 9-mesityl-10-phenylacridine tetrafluoroborate (0.02 mmol, purity 99.99%), trifluoroethanol (5 mL, chromatographically pure), (PhS) 2 (0.05 mmol, 99.99% purity)) and diisopropylethylamine (0.2 mmol, 99.99% purity), under 30W of blue LED illumination and helium atmosphere, stirring at room temperature for 30h, detecting complete reaction by TLC, concentrating the mixed solution after reaction under reduced pressure to obtain residue, and separating the residue by silica gel column chromatography, wherein the eluent of the silica gel column chromatography is a mixed solution of n-hexane and ethyl acetate (the volume ratio of n-hexane to ethyl acetate is 100]Furan p-methoxyphenyl methane.
The nuclear magnetic characterization of the product prepared in this example is shown in fig. 5-6, and the nuclear magnetic data is: 1 H NMR(400MHz,CDCl 3 )δ:7.47(d,J＝8.4Hz,1H),7.42-7.39(m,1H),7.36(s,1H),7.30-7.26(m,1H),7.22-7.15(m,3H),6.86-6.81(m,2H),4.00(s,2H),3.82(s,3H)； 13 C NMR(100MHz,CDCl 3 )δ:158.0,155.4,142.1,131.2,129.5,128.1,124.1,122.2,120.1,119.9,113.9,111.4,55.2,29.3。
from the nuclear magnetic data, the 3-arylmethylbenzo [ b ] furan compound having the target structure was prepared in this example.
Comparative example 1
O-haloaryl ether compound (0.5 mmol), K 3 PO 4 (1 mmol), tetrabutylammonium bromide (0.5 mmol) and [ Pd (COD) Cl 2 ](2 mol%) into a dry Schlenk reaction tube with a stirrer, adding 1.5mL of freshly distilled dimethylacetamide under the protection of nitrogen, and then heating to 120 ℃ for 24 hours; after the reaction is finished, cooling to room temperature, adding 3mL of water to quench the reaction, extracting with ethyl acetate, drying an organic layer with anhydrous sodium sulfate, filtering, removing the solvent under reduced pressure, and separating the obtained crude product by column chromatography to obtain the 3-benzyl benzo [ b ] b]And (3) furan.
From the above embodiments, the invention provides a method for synthesizing a 3-arylmethylbenzo [ b ] furan compound under blue light excitation, compared with the comparative example 1 (existing synthesis method), the method provided by the invention uses a photocatalyst to catalyze decarboxylation cyclization of ortho-alkynyl phenoxyacetic acid, and the whole reaction process does not need a metal catalyst and a dangerous peroxy compound, so that the reaction safety is high, and the cost is low; the whole reaction process can be finished at room temperature without heating, and the reaction condition is mild; the whole reaction process does not need strong acid and strong base.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (7)
1. A method for synthesizing a 3-arylmethylbenzo [ b ] furan compound under blue light excitation comprises the following steps:
mixing an o-alkynyl phenoxyacetic acid compound, a photocatalyst, a free radical regulator, alkali and a reaction solvent, and carrying out cyclization reaction under the condition of blue light irradiation to obtain a 3-arylmethylbenzofuran compound;
the temperature of the cyclization reaction is room temperature; the alkali is diisopropylethylamine, pyridine or triethylamine;
the o-alkynyl phenoxyacetic acid compound has a structure shown in a formula I:
the 3-arylmethylbenzo [ b ] furan compound has a structure shown in formula II:
in the formulas I and II, R is-H; r 1 independently-H, -Me or-OMe;
the photocatalyst is 9-mesityl-10-phenylacridine tetrafluoroborate;
the free radical regulator is (PhS) 2 ；
The cyclization reaction was carried out under a helium atmosphere.
2. The method of claim 1, wherein the reaction solvent comprises trifluoroethanol, acetonitrile, methanol, or dimethyl sulfoxide.
3. The method according to claim 1 or 2, wherein the molar ratio of the o-alkynyl phenoxyacetic acid compound to the photocatalyst to the free radical regulator to the base is 1 (0.05-0.2) to (0.15-0.4) to (0.5-2).
4. The method of claim 3, wherein the dosage ratio of the o-alkynyl phenoxyacetic acid compound to the reaction solvent is 0.2mmol (2-10) mL.
5. The method of claim 1, wherein the blue light illumination is at a power of 20W to 30W, and wherein the blue light illumination is achieved by blue LED illumination.
6. The process according to claim 1, wherein the cyclization reaction is carried out for 24 to 36 hours.
7. The method of claim 1, further comprising, after completing the cyclization reaction: and (3) sequentially carrying out reduced pressure concentration and silica gel column chromatography separation on the mixed solution obtained by the reaction to obtain the 3-arylmethylbenzofuran compound.
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| WO2016196931A1 (en) * | 2015-06-05 | 2016-12-08 | The Trustees Of Princeton University | Decarboxylative conjugate additions and applications thereof |
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| CN106242934A (en) * | 2016-07-26 | 2016-12-21 | 云南民族大学 | A kind of β position C H key acetoxylation synthetic method of ketone |
| CN106831530A (en) * | 2016-12-29 | 2017-06-13 | 兰州大学 | A kind of method that generation based on acyl group free radical prepares disubstituted Oxoindole |
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