Four-electron homogeneous reducing agent, preparation method and applications thereof

A reducing agent and electron technology, applied in the preparation of reducing agent, the field of homogeneous reducing agent, can solve problems such as restricting the research of chemical properties and uses, and achieve the effects of good chemical stability, environmental friendliness and safe use

Active Publication Date: 2019-12-31
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Silole compounds (silacyclopentadiene compounds), due to their unique chemical and photoelectric properties, have been widely used in the fields of optical devices, chemical sensing, biomonitoring, cell imaging, and stimulating nano-responsive materials, especially Its lower LUMO orbital energy makes it easy to obtain electrons, which can be reduced by alkali metals to generate silole anion compounds, and these silole anion compounds are very active at room temperature, and it is easy to react by themselves to form silole polymers, which limits the Research on its chemical properties and uses

Method used

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  • Four-electron homogeneous reducing agent, preparation method and applications thereof
  • Four-electron homogeneous reducing agent, preparation method and applications thereof
  • Four-electron homogeneous reducing agent, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Preparation of 2,3,4,5,2',3',4',5'-octaphenylspirocyclic silole tetralithium salt

[0053] Under the protection of nitrogen, metal lithium (0.30 g, 44.0 mmol) was added to 2,3,4,5,2',3',4',5'-octamol dissolved in 50 mL of ethylene glycol dimethyl ether at room temperature Phenylspirosilole (7.4 g, 10.0 mmol). React for 2h, concentrate the solution to 10mL, and place it in a refrigerator at -40°C for crystallization to obtain orange-red solid 2,3,4,5,2',3',4',5'-octaphenylspirocyclic silole Tetralithium salt 11.3g, yield 95%.

[0054] The obtained product was subjected to H NMR spectroscopy ( 1 H NMR C 6 D. 6 )like figure 1 . It can be seen from the figure that δ=6.87~7.47 ppm is the peak of the eight phenyl groups of spirocyclic silole, and δ=2.98 and δ=3.07ppm are the peaks of methylene and methyl groups on ethylene glycol dimethyl ether , Compared with the peaks of free ethylene glycol dimethyl ether (δ=3.12 and δ=3.33ppm), significant changes have ta...

Embodiment 2

[0062] The reaction of embodiment 2 spirocyclic silole tetralithium salts and diquinones

[0063] The preparation process of 2,3,4,5,2',3',4',5'-octaphenylspirosilole tetralithium salt is the same as in Example 1.

[0064] At room temperature, a solution of diquinone (0.027 g, 0.25 mmol) dissolved in 10 mL of tetrahydrofuran was added dropwise to the octaphenylspirocyclic silole tetralithium salt (0.80 g, 0.50 mmol) obtained in Example 1, and the color of the system gradually changed to colorless. Drain and make the crude product NMR shows (such as image 3 ) generates hydroquinone anion (peak at σ=9.83ppm), and the spirocyclic silole tetralithium salt is completely transformed into a spirocyclic silole compound.

[0065] It shows that the tetralithium salt of spirocyclic silole can effectively reduce diquinone as a homogeneous four-electron reducing agent, showing the properties of a homogeneous reducing agent.

Embodiment 3

[0072] The reaction of embodiment 3 spirocyclic silole tetralithium salts and methyl iodide

[0073] The preparation process of 2,3,4,5,2',3',4',5'-octaphenylspirosilole tetralithium salt is the same as in Example 1.

[0074] At room temperature, a solution of methyl iodide (0.07 g, 0.5 mmol) dissolved in 5 mL of tetrahydrofuran was added dropwise to the obtained spirocyclic silole tetralithium salt (0.40 g, 0.25 mmol, the product of Example 1) obtained in Example 1, and the system The color gradually becomes colorless. Draining and doing the NMR of the crude product showed that the reduction product methyllithium (MeLi) was generated, and the spirocyclic silole tetralithium salt was completely converted into the spirocyclic silole compound.

[0075] It shows that the tetralithium salt of spirocyclic silole can effectively reduce methyl iodide as a homogeneous four-electron reducing agent, showing the properties of a homogeneous reducing agent.

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Abstract

The invention discloses a 2,3,4,5,2',3',4',5'-octaaryl spiro silole four-anion compound with a structure represented by a formula (I), wherein Ar is C6-C10 aryl or substituted aryl, preferably one selected from phenyl, 2,6-dimethyl phenyl and 2,6-diisopropyl phenyl. According to the present invention, with the application of the compound as a reducing agent in diquinone, bis(triphenylphosphine)palladium dichloride, methyl iodide and an oxygen system, the compound shows efficient reducing performance, and the reducing agent is good in thermal stability, solubility and chemical stability; the preparation method has characteristics of simpleness and high yield; and the product has characteristics of safe use, no toxicity, no odor and environmental protection, and has wide application prospectin homogeneous reducing agents. The invention further discloses a preparation method and applications of the aryl spiro silole four-anion compound.

Description

technical field [0001] The invention relates to a homogeneous reducing agent, a preparation method of the reducing agent and its application, in particular to a four-electron homogeneous reducing agent containing a spirocyclic silole structure, a preparation method of the reducing agent and its application. Background technique [0002] Reduction reaction is an important reaction in the field of synthetic chemistry, and it is widely used in metallurgy, chemical industry, materials and biomedicine. Currently commonly used reducing agents are mainly some alkali metals and alkaline earth metals, such as lithium (Li), sodium (Na), potassium (K), magnesium (Mg) and the like. However, the above-mentioned types of reducing agents are all heterogeneous reducing agents, and they cannot be miscible with the reaction system, so that the reaction proceeds slowly, the reaction selectivity is poor, and it is particularly easy to cause excessive reduction. The above problems can be avoide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07C37/64C07C39/08C07F1/02
CPCC07F7/0807C07F7/083C07C37/64C07F1/02C07C39/08
Inventor 韩振刚刘承琪徐人威李琰周颖王雄韩晓昱李艳芹穆蕊娟韦清华
Owner PETROCHINA CO LTD
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