Method for preparing aldehyde/ketone by breaking C-C bond

A bond breaking and C-C technology, which is applied in the field of C-C bond breaking to prepare aldehydes/ketones, can solve the problems of difficult large-scale application in industrial production, industrial application restrictions, and high price.

Active Publication Date: 2021-11-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this reaction needs to use expensive iridium metal as a catalyst, which is difficult to be applied in industrial production on a large scale.
In addition, noble metal complex catalysts such as ruthenium and palladium have been developed in the related art for the aerobic oxid

Method used

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  • Method for preparing aldehyde/ketone by breaking C-C bond
  • Method for preparing aldehyde/ketone by breaking C-C bond
  • Method for preparing aldehyde/ketone by breaking C-C bond

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The present embodiment has prepared a kind of phenhexanone, and concrete process is:

[0052]

[0053] At room temperature, 1-phenylcyclohexanol (0.2mmol, 1equiv), ferric chloride (0.02mmol, 0.1equiv), tetrabutylammonium chloride (0.04mmol, 0.2equiv), bis(2,4 , 6-triisopropylphenyl) disulfide (0.04mmol, 0.2equiv), 2,4,6-collidine (0.2mmol, 1equiv) and 2mL dichloroethane were added to the reaction tube, and the replacement Protective gas three times, stirring reaction 60h under the illumination of 450nm blue light, after monitoring the reaction by thin-layer chromatography, the reaction mixture was cooled, then added ethyl acetate to filter, then spin off the solvent, and obtain the product after column chromatography separation (washing Removal agent: petroleum ether: ethyl acetate = 20:1), the product is a yellow liquid with a yield of 81%.

[0054] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0055] 1 H NMR (400M...

Embodiment 2

[0060] The present embodiment has prepared a kind of phenhexanone, and concrete process is:

[0061]

[0062] At room temperature, 1-phenylcyclohexanol (0.2mmol, 1equiv), iron trichloride (0.02mmol, 0.1equiv), tetrabutylammonium chloride (0.04mmol, 0.2equiv), diphenyl disulfide Add ether (0.04mmol, 0.2equiv), 2,4,6-collidine (0.2mmol, 1equiv) and 2mL dichloroethane into the reaction tube, replace the protective gas three times, and stir the reaction under the light of 450nm blue light After 24h, after the end of the reaction was monitored by thin layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was obtained after column chromatography separation (eluent: petroleum ether: ethyl acetate=20: 1), the product is a yellow liquid, and the yield is 25%.

[0063] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0064] 1 H NMR (400MHz, Chlorofo...

Embodiment 3

[0066] The present embodiment has prepared a kind of 4-trifluoromethyl acetohexanone, and concrete process is:

[0067]

[0068] At room temperature, 1-(4-trifluoromethylphenyl)cyclohexanol (0.2mmol, 1equiv), ferric chloride (0.02mmol, 0.1equiv), tetrabutylammonium chloride (0.04mmol, 0.2 equiv), bis(2,4,6-triisopropylphenyl) disulfide (0.04mmol, 0.2equiv), 2,4,6-collidine (0.2mmol, 1equiv) and 2mL dichloroethyl Add alkane into the reaction tube, replace the protective gas three times, stir the reaction under the light of 450nm blue light for 60h, monitor the end of the reaction by thin layer chromatography, cool the reaction mixture, then add ethyl acetate to filter, then spin off the solvent, pass through the column The product was obtained after chromatographic separation (eluent: petroleum ether: ethyl acetate = 20:1), and the product was a yellow liquid with a yield of 86%.

[0069] The data of the proton nuclear magnetic resonance spectrum of gained product are as fo...

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Abstract

The invention discloses a method for preparing aldehyde/ketone by breaking a C-C bond, which comprises the following step of: in an organic solvent system under an anaerobic condition, by taking alcohol as a reaction raw material, selectively breaking a C-C bond under the combined action of an iron catalyst, organic alkali and an additive to obtain aldehyde/ketone. According to the method, the alcohol and the iron catalyst are cheap and easy to obtain, the substrate range is wide, post-treatment is simple, the yield and purity of the product are high, a new synthesis route and method are developed for aldehyde and ketone compounds, and the method has good application potential and research value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing aldehyde / ketone by C-C bond breaking. Background technique [0002] Aldehydes / ketones are a class of important biologically active molecules, which not only widely exist in pharmaceutical molecules and natural products, but also are common intermediates in organic synthesis and industry. Selective oxidation of alcohols to carbonyl compounds is an extremely important class of reactions in modern organic synthesis. The traditional method of oxidizing alcohols to aldehydes and ketones mainly uses transition metal chromium oxides, but chromium is highly toxic and expensive, and the oxidation process is difficult to control during the reaction process, prone to over-oxidation, resulting in incompatibility of sensitive groups, difficult to Large-scale use in the pharmaceutical industry. [0003] In 1978, American chemist Dainel Swern disco...

Claims

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Application Information

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IPC IPC(8): C07C45/51C07C45/54C07C67/475C07B41/06C07C49/76C07C49/80C07C49/643C07C47/225C07C47/228C07C47/54C07C49/403C07C69/04C07C47/04
CPCC07C45/512C07C45/54C07C67/475C07B41/06C07C2603/16C07C2603/26C07C49/76C07C49/80C07C49/643C07C47/225C07C47/228C07C47/54C07C49/403C07C69/04C07C47/04
Inventor 胡鹏刘玮
Owner SUN YAT SEN UNIV
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