Synthetic method of efficient high-stability catalyst for aqueous phase click reaction

A high-stability, click-reaction technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve problems affecting reaction activity and achieve high catalytic activity , less dosage, high stability effect

Inactive Publication Date: 2014-10-08
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, there are still a series of problems in the existing catalysts, such as the need to introduce a large amount of reducing agent, the need to introduce a large amount of ligands, the need to carry out in an inert environment, and the reaction activity will be affected by amino groups or halide ions, etc.

Method used

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  • Synthetic method of efficient high-stability catalyst for aqueous phase click reaction
  • Synthetic method of efficient high-stability catalyst for aqueous phase click reaction
  • Synthetic method of efficient high-stability catalyst for aqueous phase click reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0043] A method for synthesizing an efficient and highly stable aqueous phase click reaction catalyst, the steps are as follows:

[0044] (1) Add 20mL of anhydrous tetrahydrofuran to a dry 100mL round-bottomed flask, add 2mL of trimethylsilylacetylene; cool the system to -70°C under nitrogen protection, and slowly add 2.4mol / L of n-butyl lithium dropwise to it Solution 6mL, stirring reaction 5h;

[0045] (2) Add 0.4 mL of the compound (ethyl chloroformate) represented by formula (I) to the solution obtained in step (1), and allow it to recover to -30°C naturally, and react for 15 hours; after the reaction, use ammonium chloride to saturate The solution quenches the reaction, and the reaction product is extracted 3 times with ether, and the organic phases are combined, dried and concentrated to obtain a crude product; the crude product is separated using a silica gel column to obtain the compound shown in formula (II);

[0046](3) Dissolve 0.5 g of the compound represented by ...

Embodiment 2

[0050] A method for synthesizing an efficient and highly stable aqueous phase click reaction catalyst, the steps are as follows:

[0051] (1) Add 100mL of anhydrous tetrahydrofuran to a dry 250mL round-bottomed flask, add 12mL of trimethylsilylacetylene; cool the system to -78°C under nitrogen protection, and slowly add 2.4mol / L of n-butyl lithium dropwise to it 35mL, stirred and reacted for 8h;

[0052] (2) Add 2.1mL of the compound (ethyl chloroformate) represented by formula (I) to the solution obtained in step (1), and allow it to recover to -30°C naturally, keep this temperature and react for 20h; after the reaction, Use ammonium chloride saturated solution to quench the reaction, the reaction product is extracted 3 times with diethyl ether, the organic phases are combined, dried and concentrated to obtain a crude product, which is separated by a silica gel chromatographic column to obtain a compound shown in formula (II);

[0053] (3) Dissolve 2 g of the compound repres...

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Abstract

The invention discloses a synthetic method of an efficient high-stability catalyst for an aqueous phase click reaction. The synthetic method comprises the following steps of synthesizing a water-soluble multi-dentate triazole ligand by virtue of a multi-step organic reaction, and coordinating the water-soluble multi-dentate triazole ligand with copper salt to form a cuprous catalyst. Due to the special and stable structure, the catalyst has the characteristics that the water solubility is good, the catalytic efficiency is high, and the catalyst can stably exist in air, can be used in an acid or alkali environment and can effectively resist the interference of primary amine or halide ions; the efficient high-stability catalyst has bright prospects in various fields spanning over a plurality of subjects such as designed synthesis and modification of water-soluble polymers, combinatorial chemistry, surface modification, medicinal chemistry and molecular biology.

Description

technical field [0001] The present invention relates to a synthesis method of a catalyst, in particular to a synthesis method of a click reaction catalyst, in particular to a highly stable catalyst suitable for the click reaction of Cu(I) catalyzed azide and terminal alkyne in the water phase resolve resolution. Background technique [0002] The Cu(I)-catalyzed click reaction between azide and terminal alkyne is one of the most famous and representative click reactions, which belongs to a kind of 1,3 dipolar cycloaddition reaction. Because of its mild reaction conditions, less reaction interference, high reaction selectivity and high reaction efficiency, it is widely used in almost every branch of chemistry. Its most important applications focus on the design and modification of polymers, surface modification, molecular labeling and pharmaceutical combinatorial chemistry. The use of this type of reaction catalyst is divided into two categories. The first category was first...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07F1/08C07D249/04
Inventor 谭业邦陈浩侯胜珍马海俐
Owner SHANDONG UNIV
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