CN111978168A - Preparation method of novel aromatic ketone compound - Google Patents
Preparation method of novel aromatic ketone compound Download PDFInfo
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- CN111978168A CN111978168A CN202010839241.0A CN202010839241A CN111978168A CN 111978168 A CN111978168 A CN 111978168A CN 202010839241 A CN202010839241 A CN 202010839241A CN 111978168 A CN111978168 A CN 111978168A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
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- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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Abstract
The invention discloses a preparation method of a novel aromatic ketone compound, which takes an aromatic carboxylic acid compound and an aromatic olefin compound as reaction raw materials, takes triphenylphosphine as a deoxidizing reagent, takes methyl blue as a photocatalyst, and is stirred and reacted in an N, N-dimethylacetamide solvent at room temperature under the irradiation of a white light lamp and under the conditions of nitrogen atmosphere and 2,4, 6-trimethylpyridine as alkali to prepare the target product aromatic ketone compound. The method has the advantages of mild reaction conditions, simple operation, low cost, convenient purification, environmental friendliness and the like.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and pharmaceutical chemistry, and particularly relates to a preparation method of a novel aromatic ketone compound.
Background
The aromatic ketone compound is a very important organic compound, and has the structure of aromatic ketone in important medicine molecules, natural products and pesticide chemistry, so that the development of a new methodology for synthesizing aromatic ketone has very important significance. The most classical construction of aryl ketone backbones is coupling via a C-C bond (chem. soc. rev.24, 89-95); or by activating the carboxylic acid to form an acid chloride, ester or amide, etc., which is then coupled via a C-C bond (org. Lett.14, 3044-3047; Angew. chem. int. Ed.55, 2810-2814). However, the acylation process requires a large amount of acylation reagent, and the reaction conditions are harsh and complicated, which further restrict the synthetic application and process scale-up. However, aromatic carboxylic acids and aromatic olefin compounds are inexpensive and readily available, and it is highly desirable to synthesize ketone compounds by selecting them as raw materials. The invention adopts a photocatalysis method, takes cheap and easily obtained aromatic carboxylic acid and aromatic olefin as raw materials, can efficiently prepare various types of aromatic ketone compounds, and has important application prospect in the development of pharmaceutical chemistry, material chemistry and process.
Disclosure of Invention
The invention solves the technical problem of providing a preparation method of novel aromatic ketone compounds with simple process, low raw material cost and mild reaction conditions.
The invention adopts the following technical scheme for solving the technical problems, and the preparation method of the novel aromatic ketone compound is characterized by comprising the following specific processes: taking an aromatic carboxylic acid compound and an aromatic olefin compound as reaction raw materials, taking triphenylphosphine as a deoxidizing reagent, taking methyl blue as a photocatalyst, stirring and reacting in an N, N-dimethylacetamide solvent at room temperature under the irradiation of a white light lamp and under the conditions of a nitrogen atmosphere and 2,4, 6-trimethylpyridine as an alkali to obtain a target product, namely an aromatic ketone compound, wherein the reaction equation in the preparation process is as follows:
wherein Ar is phenyl, substituted phenyl or naphthalene ring group, the substituent on the benzene ring of the substituted phenyl is methoxy, fluorine, chlorine, bromine, methyl, nitro, isopropyl or trifluoromethyl, and the substituent is positioned at ortho-position, meta-position or para-position on the benzene ring;
r is phenyl, substituted phenyl,
Or naphthyl group, the substituent on the benzene ring of the substituted phenyl is methoxy, methyl, isopropyl, fluorine, chlorine, bromine, nitro or trifluoromethyl, and the substituent is positioned at ortho-position, meta-position or para-position on the benzene ring;
the structure of the photocatalyst is as follows:
further, the feeding molar ratio of the aromatic carboxylic acid compounds to the aromatic olefin compounds is 1: 1-3.
Further limiting, the dosage of the photocatalyst is 1 to 10 percent of the molar weight of the aromatic carboxylic acid compounds, and is preferably 2 percent.
Further, the 2,4, 6-trimethylpyridine is used in an amount of 1 to 3 times the equivalent of the aromatic carboxylic acid compound.
Compared with the prior art, the invention has the following advantages: the method has the advantages of mild reaction conditions, simple operation, low cost, convenient purification, environmental friendliness and the like.
Detailed Description
The present invention is described in further detail below with reference to examples, but it should not be construed that the scope of the above subject matter of the present invention is limited to the following examples, and that all the technologies realized based on the above subject matter of the present invention belong to the scope of the present invention.
Example 1
Weighing
(30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 36mg of the objective product
The yield was 75%.
Example 2
Weighing
(24mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 31mg of the objective product
The yield was 73%.
Example 3
Weighing
(28mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 30mg of the objective product
The yield was 65%.
Example 4
Weighing
(31mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 30mg of the objective product
The yield was 62%.
Example 5
Weighing
(40mg, 0.2mmol), photocatalyst methyl blue (5).6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 43mg of the objective product
The yield was 75%.
Example 6
Weighing
(27mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 36mg of the objective product
The yield was 80%.
Example 7
Weighing
(33mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to the reaction flask and replacedAnd 3, dissolving styrene (31mg, 0.3mmol) in 2mL of N, N-dimethylacetamide solvent for three times under nitrogen, slowly adding the solution into a reaction flask under the nitrogen atmosphere, placing the reaction flask under white light LEDs, and reacting for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 34mg of the objective product
The yield was 67%.
Example 8
Weighing
(35.6mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-collidine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 44mg of the objective product
The yield was 83%.
Example 9
Weighing
(27mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were charged into a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent under a nitrogen atmosphere,slowly adding the mixture into a reaction bottle, placing the reaction bottle under white light LEDs, and reacting for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 31mg of the objective product
The yield was 70%.
Example 10
Weighing
(28mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 33mg of the objective product
The yield was 72%.
Example 11
Weighing
(31mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction is finished, 15 is addedExtracting with ethyl acetate (3 × 10mL), standing, separating layers, pouring out lower water phase, mixing organic phases, drying the organic phase with anhydrous sodium sulfate, evaporating to dryness, loading, and performing column chromatography (petroleum ether: ethyl acetate) to obtain 34mg of target product
The yield was 73%.
Example 12
Weighing
(28mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 43mg of the objective product
The yield was 75%.
Example 13
Weighing
(33mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction was complete, 15mL of water was added, extracted with ethyl acetate (3X10mL), allowed to stand, the layers separated, the lower aqueous phase decanted, the organic phases combined and the organic phase usedDrying with anhydrous sodium sulfate, evaporating to remove organic phase, loading, and performing column chromatography (petroleum ether: ethyl acetate) to obtain 32mg of target product
The yield was 62%.
Example 14
Weighing
(38mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 39mg of the objective product
The yield was 70%.
Example 15
Weighing
(35.6mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-collidine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 40mg of the targetProduct of
The yield was 75%.
Example 16
Weighing
(30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 36mg of the objective product
The yield was 75%.
Example 17
Weighing
(30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 34mg of the objective product
The yield was 70%.
Example 18
Weighing
(30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 34mg of the objective product
The yield was 70%.
Example 19
Weighing
(28mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 31mg of the objective product
The yield was 68%.
Example 20
Weighing
(31mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 31mg of the objective product
The yield was 63%.
Example 21
Weighing
(28mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 41mg of the objective product
The yield was 71%.
Example 22
Weighing
(33mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 31mg of the objective product
The yield was 60%.
Example 23
Weighing
(38mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction is finished, 15mL of water is added, ethyl acetate (3x10mL) is used for extraction, standing is carried out, layers are separated, the lower water phase is poured out, the organic phase is combined, the organic phase is dried by anhydrous sodium sulfate, the organic phase is evaporated to dryness, the dry sample loading is carried out, and the column chromatography (petroleum ether: ethyl acetate) is carried out to obtain 32mg of target product
The yield was 58%.
Example 24
Weighing
(35.6mg, 0.2mmol), photocatalyst methyl blue (5).6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were added to a reaction flask, nitrogen was replaced three times, styrene (31mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs and reacted at room temperature for 24-36 h. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 33.5mg of the objective product
The yield was 63%.
Example 25
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(40mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white light LEDs for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 40.5mg of the objective product
The yield was 75%.
Example 26
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(35.4mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 40mg of the objective product
The yield was 78%.
Example 27
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(48mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white light LEDs for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 45mg of the objective product
The yield was 76%.
Example 28
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(36mg, 0.3mmol) was dissolved in 2mAnd (3) slowly adding the L N, N-dimethylacetamide solvent into a reaction bottle in a nitrogen atmosphere, placing the reaction bottle under white light LEDs, and reacting for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 38mg of the objective product
The yield was 74%.
Example 29
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(41.4mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 39mg of the objective product
The yield was 71%.
Example 30
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(54.3mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, and slowly added to a reaction flask under a nitrogen atmosphereAnd (4) placing the reaction flask under white light LEDs, and reacting for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 47mg of the objective product
The yield was 75%.
Example 31
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(44.7mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 44mg of the objective product
The yield was 78%.
Example 32
P-methoxybenzoic acid (30mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed out into a reaction flask, nitrogen was replaced three times, and the mixture was poured into a flask
(51.6mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs for 24-36h at room temperature. After the reaction is finished, addingAdding 15mL of water, extracting with ethyl acetate (3X10mL), standing, separating layers, pouring out the lower aqueous phase, combining the organic phases, drying the organic phase with anhydrous sodium sulfate, evaporating to dryness, loading by dry method, and performing column chromatography (petroleum ether: ethyl acetate) to obtain 44mg of target product
The yield was 72%.
Example 33
Naphthoic acid (34.4mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed into a reaction flask, nitrogen was replaced three times, and the mixture was poured into the flask
(35.7mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 37mg of the objective product
The yield was 68%.
Example 34
Naphthoic acid (34.4mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed into a reaction flask, nitrogen was replaced three times, and the mixture was poured into the flask
(40.5mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs for 24-36h at room temperature. After the reaction was complete, 15mL of water was added, extracted with ethyl acetate (3 × 10mL), allowed to stand, the layers separated, the lower aqueous phase was decanted, the organic phases were combined,drying the organic phase with anhydrous sodium sulfate, evaporating to dryness, loading, and performing column chromatography (petroleum ether: ethyl acetate) to obtain 44mg of target product
The yield was 75%.
Example 35
Naphthoic acid (34.4mg, 0.2mmol), photocatalyst methyl blue (5.6mg, 2%), 2,4, 6-trimethylpyridine (24mg, 0.2mmol) and triphenylphosphine (78.6mg, 0.3mmol) were weighed into a reaction flask, nitrogen was replaced three times, and the mixture was poured into the flask
(46.2mg, 0.3mmol) was dissolved in 2mL of N, N-dimethylacetamide solvent, slowly added to the reaction flask under nitrogen atmosphere, and the reaction flask was placed under white LEDs for 24-36h at room temperature. After the reaction, 15mL of water was added, extraction was performed with ethyl acetate (3X10mL), standing was performed, layers were separated, the lower aqueous phase was poured out, the organic phase was combined, the organic phase was dried with anhydrous sodium sulfate, the organic phase was evaporated to dryness, dry-loading was performed, and column chromatography (petroleum ether: ethyl acetate) was performed to obtain 48mg of the objective product
The yield was 78%.
The foregoing embodiments illustrate the principles, principal features and advantages of the invention, and it will be understood by those skilled in the art that the invention is not limited to the foregoing embodiments, which are merely illustrative of the principles of the invention, and that various changes and modifications may be made therein without departing from the scope of the principles of the invention.
Claims (5)
1. A preparation method of novel aromatic ketone compounds is characterized by comprising the following specific steps: taking an aromatic carboxylic acid compound and an aromatic olefin compound as reaction raw materials, taking triphenylphosphine as a deoxidizing reagent, taking methyl blue as a photocatalyst, stirring and reacting in an N, N-dimethylacetamide solvent at room temperature under the irradiation of a white light lamp and under the conditions of a nitrogen atmosphere and 2,4, 6-trimethylpyridine as an alkali to obtain a target product, namely an aromatic ketone compound, wherein the reaction equation in the preparation process is as follows:
wherein Ar is phenyl, substituted phenyl or naphthalene ring group, the substituent on the benzene ring of the substituted phenyl is methoxy, fluorine, chlorine, bromine, methyl, nitro, isopropyl or trifluoromethyl, and the substituent is positioned at ortho-position, meta-position or para-position on the benzene ring;
r is phenyl, substituted phenyl,
Or naphthyl group, the substituent on the benzene ring of the substituted phenyl is methoxy, methyl, isopropyl, fluorine, chlorine, bromine, nitro or trifluoromethyl, and the substituent is positioned at ortho-position, meta-position or para-position on the benzene ring;
the structure of the photocatalyst is as follows:
2. the process for producing the novel aromatic ketone compound according to claim 1, wherein: the feeding molar ratio of the aromatic carboxylic acid compounds to the aromatic olefin compounds is 1: 1-3.
3. The process for producing the novel aromatic ketone compound according to claim 1, wherein: the dosage of the photocatalyst is 1 to 10 percent of the molar weight of the aromatic carboxylic acid compounds.
4. The process for producing the novel aromatic ketone compound according to claim 1, wherein: the dosage of the photocatalyst is 2 percent of the molar weight of the aromatic carboxylic acid compounds.
5. The process for producing the novel aromatic ketone compound according to claim 1, wherein: the dosage of the 2,4, 6-trimethylpyridine is 1-3 times of the equivalent of the aromatic carboxylic acid compounds.
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