Method for synthesizing polysubstituted phosphono-1,3-butadiene compound

A compound, butadiene technology, applied in the field of organic synthesis and catalysis, can solve the problems of element waste, low yield, long reaction time, etc.

Inactive Publication Date: 2021-07-06
YANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, these methods have some problems to varying degrees, including high substrate restriction, long reaction time, low yield, many by-products, and not all elements participate in the reaction, and there is waste of elements. These factors It leads to high reaction cost and heavy pollution, which does not conform to the concept of green environmental protection and the concept of atomic economics, and is not suitable for industrial production.

Method used

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  • Method for synthesizing polysubstituted phosphono-1,3-butadiene compound
  • Method for synthesizing polysubstituted phosphono-1,3-butadiene compound
  • Method for synthesizing polysubstituted phosphono-1,3-butadiene compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Weigh 40.44mg (0.2mmol) diphenylphosphine oxide, 13.1mg (0.02mmol) Ni(PPh 3 ) 2 Cl 2 , 52.8mg (0.3mmol) 1-chloro-4-(3-methylbut-3-en-1-ynyl) benzene, 130.3mg (0.4mmol) Cs 2 CO 3 , 4.76mg (0.024mmol) of 1,10-phenanthroline was put into a reaction flask, and 2mL of methanol solution was added, and placed under the irradiation of a 23W blue LED lamp under the protection of argon, the reaction was stirred at room temperature, and the progress of the reaction was detected by TLC. After about 24 hours, it was detected that the reaction was over, and the reacted solution was separated and purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain a white liquid, which was the product (E)-(1-(4-chlorobenzene yl)-3-methylbut-1,3-dienyl)diphenylphosphine oxide, yield: 75%.

[0034] The product is carried out infrared test, the result is as follows figure 1 Shown, IR (neat): ν = 3059, 2925, 2857, 2218, 1487, 1437, 1187, 1108, 705, 555cm -1 .

[0035]...

Embodiment 2

[0041] Embodiment 2: the impact of different solvents on product yield

[0042] Reaction condition is with embodiment 1, and solvent adopts any one in dichloroethane (DCE), acetonitrile (MeCN), methyl alcohol (MeOH) and acetone (Acetone) respectively, and product yield is shown in table 1 below:

[0043] The impact of different solvents in table 1 on product yield

[0044] Solvent (2mL) DCE Acetone MeOH MeCN Yield(%) less than 5 No reaction 75 25

[0045] As can be seen from Table 1, when other reaction conditions remain unchanged and the solvent is methanol, the highest product yield is 75%, indicating that methanol has good selectivity for this reaction.

Embodiment 3

[0046] Embodiment 3: the impact of different photocatalysts on product yield

[0047] Reaction condition is with embodiment 1, uses respectively Ni (PPh 3 ) 2 Cl 2 , Ni(PPh 3 ) 2 Br 2 、NiBr 2 and NiCl 2 Any one of them, the product yields are shown in Table 2 below.

[0048] Table 2 Effect of different photocatalysts on product yield

[0049] Catalyst (0.02mmol) Ni(PPh 3 ) 2 Br 2

[0050] It can be seen from Table 2 that when other reaction conditions remain unchanged, only Ni(PPh 3 ) 2 Cl 2 Products are produced, and the productive rate is 75%, indicating that Ni(PPh 3 ) 2 Br 2 There is good selectivity for this reaction.

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Abstract

The invention discloses a method for synthesizing a polysubstituted phosphono-1,3-butadiene compound. The method comprises the following steps: dissolving a disubstituted phosphorus oxide compound, a 1,3-enyne compound, inorganic alkali, a dinitrogen-containing aromatic heterocyclic compound ligand and a metal nickel complex photocatalyst in a solvent, conducting a stirring reaction under the protection of inert gas and under the condition of room temperature and illumination, and after the reaction is completed, carrying out column chromatography separation and purification to obtain the compound. The method has the advantages of mild reaction conditions, high yield, simplicity in operation, convenience in subsequent treatment, usage of a novel catalyst and the like.

Description

technical field [0001] The invention relates to a method for synthesizing multi-substituted phosphono 1,3-butadiene compounds, belonging to the technical field of organic synthesis and catalysis. Background technique [0002] Organophosphorus compounds play a key role in organic synthesis, pesticide chemistry, materials and catalysis, so it is of great significance to study the preparation of organophosphorus compounds. Phosphono-1,3-dienes and their derivatives with pre-functionalized phosphorus compounds are easy to carry out subsequent functional group transformation, and synthesize a variety of compounds with potential practical value. It can undergo Micheal-addition reaction with nucleophile to form allylphosphine compound, and undergo Diels-Alder reaction with dienophile to form cyclic compound and so on. [0003] Conventional methods for synthesizing phosphono-1,3-dienes mainly focus on the elimination reaction of the simplest phosphine-containing allyl alcohol under...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/53C07F9/58C07F9/6553
CPCC07F9/5325C07F9/58C07F9/655345
Inventor 侯虹周冰朱绍群
Owner YANGZHOU UNIV
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