Quinone-catalyzed trifluoromethylation photocatalytic synthesis method

A technology of trifluoromethylated photo-synthesis method, which is applied in the field of photocatalytic organic synthesis, can solve the problems of high pollution and high cost, achieve low environmental pollution, overcome consumption, and be beneficial to large-scale industrial production

Active Publication Date: 2016-04-20
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a photocatalytic synthesis method of a trifluoromethylation product with simple system, mild reaction conditions, low cost and mass production, and to solve the high pollution and high cost problems of industrial trifluoromethylation reaction

Method used

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  • Quinone-catalyzed trifluoromethylation photocatalytic synthesis method
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  • Quinone-catalyzed trifluoromethylation photocatalytic synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Mix monocyclic quinones (different quinones) and sodium trifluoromethanesulfinate with a molar ratio of 100:200; take the mixed sample in a manganese dioxide fixed-bed reactor, and then mix 15ml of acetonitrile and 10ml of benzene Pour in the reactor, under air atmosphere, 800mW visible light irradiation 12h, obtain the product liquid of uniform transparency; Figure 4 Shown; The mass spectrometry and nuclear magnetic resonance spectra of the product liquid are as figure 1 , 2 shown).

Embodiment 2

[0033] Mix benzoquinone and sodium trifluoromethyl sulfinate with a molar ratio of 100:200; take the mixed sample in a manganese dioxide fixed-bed reactor, then pour 15ml of acetonitrile and 10ml of benzene into the reactor, in an air atmosphere Under the condition of light intensity ranging from 200-800mW, visible light ranging from light wavelength 420-780nm was irradiated for 10h to obtain a uniform and transparent product liquid. (it records reaction light intensity by light meter, records the ultraviolet absorption diffuse reflectance spectrum of quinone catalyst by DRS. The relation of reaction light intensity, reaction wavelength and product yield is as follows Figure 5 Shown; The mass spectrometry and nuclear magnetic resonance spectra of the product liquid are as figure 1 , 2 shown).

Embodiment 3

[0035] Mix monocyclic quinones and sodium trifluoromethanesulfinate with a molar ratio of 100:200; take the mixed sample in a manganese dioxide fixed-bed reactor, then mix 15ml of acetonitrile and 10ml of 5,6-dimethoxy Base-1-indanone (Aricept drug precursor) was poured into the reactor, and 800mW of visible light of different wavelengths was irradiated for 15 hours under an air atmosphere to obtain a uniform and transparent product liquid. (mass spectrum, nuclear magnetic resonance spectrum of product liquid such as Figure 6 , 7 shown).

[0036] The GC-MS spectrogram of the trifluorotoluene that the present invention reacts obtains ( figure 1 ) The peak at 2.5 min was matched to trifluorotoluene. After repeating the experiment, by nuclear magnetic resonance, 19 F spectrum ( figure 2 ) Analysis 62.68ppm place is the standard trifluorotoluene peak. Trifluoromethylation reaction with 5,6-dimethoxy-1-indanone (Aricept drug precursor) as substrate, we obtained a variety of...

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Abstract

The invention discloses a quinone-catalyzed trifluoromethylation photocatalytic synthesis method. According to the method, the using problem of highly-corrosive and highly-toxic fluorinating reagents such as hydrogen fluoride and sulfur tetrafluoride in an existing industrial trifluoromethylation reaction is solved, the heavy metal pollution problem of a catalyst in industry is avoided, and the good actual application prospect is achieved. The metal-free photocatalytic trifluoromethylation reaction is achieved by taking simplest and cheapest benzoquinone and derivatives thereof as a photocatalyst and taking a Langlois reagent-sodium trifluoromethanesulfinate (CF3SO2Na) as a trifluoromethyl source under the mild visible light condition, and a complete full-cycle reaction is achieved through a homemade fixed bed reactor. Trifluoromethyl modification can be further performed on organic molecules with the bioactivity and the pharmaceutical activity according to the actual needs. The method has the advantages that the synthesis condition is mild, the raw materials are cheap and easy to obtain, the environmental pollution is low, large-scale industrial production is facilitated, and the significant economic and social benefit is achieved.

Description

technical field [0001] The invention belongs to the technical field of photocatalytic organic synthesis, and in particular relates to a quinone-catalyzed trifluoromethylated photocatalytic organic synthesis method. Background technique [0002] In recent years, with the continuous development of organic fluorine chemistry, fluorine-containing organic compounds have been widely studied and applied in the fields of medicine, pesticides, and functional materials. The introduction of fluorine-containing groups into drug molecules will change its charge distribution, enhance its fat solubility and the acidity of adjacent groups, and then enhance the metabolic stability, affinity binding and membrane permeability of drugs (Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886). Therefore, the development of novel and efficient organofluorine chemical reactions, especially trifluoromethylation reactions, has long attracted the interest of chemical researchers. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/00C07C25/13B01J31/02
CPCB01J31/0205B01J35/004B01J2231/40C07C17/00C07C25/13
Inventor 员汝胜常彬邱文朝邵鸿鸽王乐乐陈旬
Owner FUZHOU UNIV
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