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Method for photocatalytic reduction cross-coupling of aromatic olefin and halogenated hydrocarbon

A cross-coupling and aromatic technology, applied in the field of photocatalytic organic synthesis, can solve the problems that have not yet been reported, and achieve good yield, high photocatalytic conversion efficiency, and simple and easy-to-operate reaction conditions

Pending Publication Date: 2022-04-15
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These reports only achieved the reduction of aromatic olefins, but there is no related report on the reduction of aromatic olefins and coupling with halogenated hydrocarbons by photocatalysis.

Method used

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  • Method for photocatalytic reduction cross-coupling of aromatic olefin and halogenated hydrocarbon
  • Method for photocatalytic reduction cross-coupling of aromatic olefin and halogenated hydrocarbon
  • Method for photocatalytic reduction cross-coupling of aromatic olefin and halogenated hydrocarbon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Add 10 mg of 15% Cu with an average particle size of 4 nm to the pyrex tube 2+ -MPA-CdS photocatalyst, 115μL (1mmol) styrene, 105μL (1mmol) bromobenzene, 224mg (4mmol) potassium hydroxide, 5mL methanol and deionized water volume ratio of 1:1 mixed solvent, mix well, make the system In a sealed nitrogen atmosphere, irradiate with a 420nm LED lamp for 12 hours to obtain 1,2-diphenylethane with a yield of 62%, and the structural characterization data are: 1 H NMR (400MHz, CDCl 3 ): δ7.34-7.24(m,4H), 7.20(dd,6H), 2.92(s,4H), see figure 1 ; 13 C NMR (400MHz, CDCl 3 ): δ141.8, 128.4, 128.3, 125.9, 37.9, see figure 2 .

Embodiment 2

[0025]

[0026] In this example, the styrene in Example 1 was replaced with 133 μL (1 mmol) 4-methoxystyrene, and the other steps were the same as in Example 1 to obtain 1-methoxy-4-(2-phenylethyl) Benzene, its yield is 87%, and the structural characterization data is: 1 H NMR (400MHz, CDCl 3 ):δ7.34-7.28(m,2H),7.22(ddd,,3H),7.15-7.07(m,2H),6.89-6.82(m,2H),3.81(s,3H),2.91(d, 4H); 13 C NMR (400MHz, CDCl 3 ): δ157.8, 141.8, 133.9, 129.3, 128.4, 128.3, 125.8, 113.7, 55.2, 38.2, 37.0.

Embodiment 3

[0028]

[0029] In this example, 131 μL (1 mmol) of 4-chlorostyrene was used to replace the styrene in Example 1, and the other steps were the same as in Example 1 to obtain 1-chloro-4-(2-phenylethyl)benzene, which produced The ratio is 40%, and the structural characterization data are: 1 H NMR (400MHz, CDCl 3 ):δ7.30-7.17(m,5H),7.16-7.11(m,2H),7.10-7.03(m,2H),2.88(s,4H); 13 C NMR (400MHz, CDCl 3 ): δ141.2, 140.1, 131.6, 129.8, 128.4, 128.4, 128.3, 126.0, 37.7, 37.2.

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Abstract

According to the method, a water-soluble copper ion-doped cadmium sulfide quantum dot is used as a photocatalyst, water is used as a proton source in a system, the aromatic olefin and the halogenated hydrocarbon are used as substrates, and the reduction cross-coupling of the aromatic olefin and the halogenated hydrocarbon is realized. The invention aims to realize visible light driven aromatic olefin reduction of a water phase system and realize cross coupling with halogenated hydrocarbon to construct a C-C bond. The photocatalyst disclosed by the invention is synthesized by utilizing cheap and easily available raw materials and adopting a simple and easy-to-operate experimental method, the photocatalytic reaction does not need to use a noble metal material as a cocatalyst, the construction of a C-C bond can be realized under a mild condition, and the photocatalyst can be applied to synthesis of drugs and production of chemical value-added products.

Description

technical field [0001] The invention belongs to photocatalytic organic synthesis, and in particular relates to a quantum dot used as a photocatalyst to realize the reductive cross-coupling reaction of aromatic olefins and halogenated hydrocarbons. Background technique [0002] Organic synthesis plays a vital role in human production and life. Using organic synthesis, we can obtain the medicines, food preservatives, pesticides, fertilizers, etc. we need every day. However, traditional organic synthesis reactions not only involve multi-step synthetic routes, but also usually require some toxic and strong oxidizing agents or reducing agents. In recent years, researchers have discovered that photocatalysis can be used to catalyze substrate reactions at room temperature without the need for high temperature and high pressure experimental conditions, reducing energy consumption; the highlight of photocatalytic organic reactions is that the reaction only needs to add photocatalysts...

Claims

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Application Information

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IPC IPC(8): B01J27/04C07C2/86C07C15/16C07C41/24C07C43/205C07C17/269C07C25/18C07C43/275C07D213/16
Inventor 王红艳谢伟华韦东东
Owner SHAANXI NORMAL UNIV
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