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Preparation method of thermal-sensitive type catalyst used for asymmetric hydrogen transfer reaction

A catalyst and hydrogen transfer technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problems of separation and recovery of chiral metal complex catalysts that have not been well resolved, and achieve Overcome the difficult purification of products, the difficulty of catalyst recovery, high catalytic activity and enantioselectivity

Inactive Publication Date: 2016-08-24
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although homogeneous asymmetric hydrogen transfer has achieved great success, the problem of separation and recovery of expensive chiral metal complex catalysts has not been well resolved.

Method used

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  • Preparation method of thermal-sensitive type catalyst used for asymmetric hydrogen transfer reaction
  • Preparation method of thermal-sensitive type catalyst used for asymmetric hydrogen transfer reaction
  • Preparation method of thermal-sensitive type catalyst used for asymmetric hydrogen transfer reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] A kind of preparation method of temperature-sensitive catalyst for asymmetric hydrogen transfer reaction

[0014] Add 0.293g of raw material 9-aminoepicincholine, 1.13g of N-isopropylacrylamide, 0.033g of initiator azobisisobutyronitrile and 17mL of absolute ethanol into the reaction vessel in sequence, stir to dissolve, and pass nitrogen gas to remove oxygen , heated to 70°C and reacted for 48h. After the reaction, the solvent was removed by rotary evaporation, 5mL of acetone was added, and 100ml of diethyl ether was used as a precipitant to precipitate the product, filtered by suction, and dried to obtain 9-aminoepicinchonine and N-isopropylpropene Copolymers of amides where x:y=1:10. Under a nitrogen atmosphere, 0.525 g of the copolymer, 0.021 g of 1,5-cyclooctadiene iridium chloride dimer, and 5 ml of isopropanol were added into a reaction vessel, and stirred at room temperature for 4 hours to obtain a catalyst.

Embodiment 2

[0016] A kind of preparation method of temperature-sensitive catalyst for asymmetric hydrogen transfer reaction

[0017] Add 0.293g of the raw material 9-aminoepichonine, 0.567g of N-isopropylacrylamide, 0.016g of the initiator azobisisobutyronitrile and 11ml of absolute ethanol into the reaction vessel in sequence, stir to dissolve, and pass through nitrogen to remove oxygen , heated to 70°C and reacted for 48h. After the reaction, the solvent was removed by rotary evaporation, 2.5mL of acetone was added, and 50ml of ether was used as a precipitating agent to precipitate the product, suction filtered, and dried to obtain 9-aminoepichonine and N-isopropyl Copolymers of acrylamide where x:y=1:5. Under a nitrogen atmosphere, 0.315 g of the copolymer, 0.021 g of 1,5-cyclooctadiene iridium chloride dimer, and 5 ml of isopropanol were added into a reaction vessel, and stirred at room temperature for 4 hours to obtain a catalyst.

Embodiment 3

[0019] Dissolve 0.11 g of the prepared catalyst and 1.4 mg of potassium hydroxide in 5 ml of isopropanol, stir for 0.5 h, add 29 μL of acetophenone, and react at 25° C. for 180 min (see Table 1 for catalytic performance data). After the reaction, 6ml of water was added, and the temperature was raised to 40° C. to recover the catalyst by centrifugation.

[0020] The reaction formula is:

[0021]

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PUM

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Abstract

The invention relates to a preparation method of a thermal-sensitive type catalyst used for an asymmetric hydrogen transfer reaction. The method comprises the steps that azodiisobutyronitrile serves as an initiator, a thermal-sensitive type polymer is obtained through 9-amine cinchonine and N-isopropylmethacylamide, complexation is conducted on the polymer and an iridium compound, and the catalyst is obtained. The prepared catalyst can be used for an acetophenone asymmetric hydrogen transfer reaction, and the high catalytic activity and enantioselectivity are achieved. The catalyst has the thermal-sensitive characteristic, after the reaction is finished, separation and recycling are easy, and reutilization is achieved. According to the preparation method of the thermal-sensitive type catalyst used for the asymmetric hydrogen transfer reaction, an effective way is provided for separation and recycling of a metal organic complex catalyst, and a wide application prospect is achieved.

Description

technical field [0001] The invention relates to a method for preparing a temperature-sensitive catalyst for asymmetric hydrogen transfer reaction. The temperature-sensitive characteristic of the catalyst can be used for the separation and recovery of the catalyst after the reaction. Background technique [0002] Due to its unique chiral multiplication, asymmetric catalysis is the most economical and effective in many asymmetric synthesis reactions, and has the most value for research and development. frontier research areas. Chiral secondary alcohols are a very important class of intermediates in organic synthesis and are widely used in the synthesis of fine chemicals such as pharmaceuticals, pesticides and spices. The asymmetric hydrogen transfer reaction of hypochiral ketones catalyzed by chiral transition metal complexes is one of the effective ways to prepare chiral secondary alcohols with mild reaction conditions and easy operation. However, although homogeneous asymm...

Claims

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Application Information

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IPC IPC(8): C08F220/54C08F226/06C08F8/42B01J31/22C07C29/143C07C33/22
CPCC08F220/54B01J31/165B01J31/1835B01J2231/60C07C29/143C08F8/42
Inventor 楼兰兰刘双喜李珊珊于文军张炯杨婷
Owner NANKAI UNIV
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