Bidentate phosphite ligand taking biphenol as structure unit and its preparation method

A technology of bidentate phosphite and structural units, which is applied in the field of preparation of bidentate phosphite ligands, can solve the problems of less research on bidentate phosphite ligands, and achieve wide application value, air insensitivity, structural stable effect

Active Publication Date: 2018-03-23
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although there are many reports on various bidentate phosphite ligands, there are few reports on the bidentate phosphite ligands with biphenol as the structural unit so far, so the synthesis of this type of compound has certain reality. and theoretical significance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The structural formula of the bidentate phosphite ligand with biphenol as the structural unit of the present embodiment is:

[0020] ;

[0021] The preparation method of the bidentate phosphite ligand with biphenol as the structural unit of the present embodiment is as follows:

[0022] (1) Add 2,2'-dihydroxybiphenyl (558mg, 3.0mmol) into a dry and clean 50mL three-neck flask, vacuumize with an oil pump and replace N 2 three times at N 2 Add 12mL of dry chlorobenzene under protection, HPMT (1.74mL, 12.00mmol), and stir at 20°C for 10h;

[0023] (2) Stop heating, and wait for the reaction solution to cool to room temperature under N 2 Add trans-cyclohexanediol (0.10mL, 1.0mmol) under protection, the reaction temperature is 25°C, the reaction time is 8 hours, filter, and the filtrate is spin-dried to obtain the product, and the recrystallization method is used to obtain 789mg of white solid, the yield 95%. Mp: 67-69 °C; 1 H NMR (600 MHz, CDCl 3 , SiMe 4 ): δ ...

Embodiment 2

[0025] The preparation method of the bidentate phosphite ligand with biphenol as the structural unit of the present embodiment is as follows:

[0026] (1) Add 2,2'-dihydroxybiphenyl (558mg, 3.0mmol) into a dry and clean 100mL three-neck flask, vacuumize with an oil pump and replace N 2 three times at N 2 Add 35mL dry toluene and HPMT (0.22mL, 1.5mmol) under protection, and stir at 150°C for 1h;

[0027] (2) Stop heating, and wait for the reaction solution to cool to room temperature under N 2 Add trans-cyclohexanediol (0.15mL, 1.5mmol) under protection, the reaction temperature is 140°C, the reaction time is 2 hours, filter, and the filtrate is spin-dried to obtain the product, and the recrystallization method is used to obtain 789mg of a white solid, the product The rate is 95%. Mp: 67-69 °C; 1 H NMR (600 MHz, CDCl 3 , SiMe 4 ): δ 7.45-7.13 (m, 16H), 4.27 (m, 2H), 2.09 (d, J = 13.8 Hz, 2H), 1.68-1.66 (m, 2H), 1.53 (t, J = 10.2 Hz, 2H), 1.25 (t, J = 9.3 Hz, 2H);...

Embodiment 3

[0029] The preparation method of the bidentate phosphite ligand with biphenol as the structural unit of the present embodiment is as follows:

[0030] (1) Add 2,2'-dihydroxybiphenyl (558mg, 3.0mmol) into a dry and clean 100mL three-neck flask, vacuumize with an oil pump and replace N 2 three times at N 2 Add 30mL of dry xylene, HPMT (1.06mL, 7.32mmol) under protection, and stir at 100°C for 3 h;

[0031] (2) Stop heating, and wait for the reaction solution to cool to room temperature under N 2 Add trans-cyclohexanediol (0.30mL, 3.0mmol) under protection, the reaction temperature is 90°C, the reaction time is 3 hours, filter, and the filtrate is spin-dried to obtain the product, and the recrystallization method is used to obtain 789mg of a white solid, the product The rate is 95%. Mp: 67-69 °C; 1H NMR (600 MHz, CDCl 3 , SiMe 4 ): δ 7.45-7.13 (m, 16H), 4.27 (m, 2H), 2.09 (d, J = 13.8 Hz, 2H), 1.68-1.66 (m, 2H), 1.53 (t, J = 10.2 Hz, 2H), 1.25 (t, J = 9.3 Hz, 2H); ...

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Abstract

The invention discloses a bidentate phosphite ligand taking biphenol as a structure unit and its preparation method. The structure formula of the ligand is as shown in the specification. The ligand iscompounded in one step through taking 2, 2'-dihydroxybiphenyl and trans-cyclohexanediol. The compounding method is simple in operation; the raw materials are low in price and easy to obtain. The ligand has the advantages of being stable in structure and not sensitive to water, air and others. The ligand has wide potential application value in many organic catalytic reactions; therefore, the bidentate phosphite ligand is expected to apply to organic compounding field.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a bidentate phosphite ligand with biphenol as a structural unit. Background technique [0002] Ligands often play a pivotal role in organocatalytic reactions, and for many reactions, the addition of a catalyst alone cannot take place. Even if the reaction can occur, harsh conditions are required, such as: high temperature, high pressure, etc. The study found that after adding a ligand to the reaction, the reaction can occur under mild conditions. In addition to this, the use of ligands enables other cases where the reaction cannot take place to be successfully realized ( Pure Appl Chem. , 2000, 18(1): 1233 ~1246). [0003] Scientists have synthesized various types of phosphite ligands with biphenol as the structural unit. In 1995, Van Leeuwen's group reported a new class of chiral bidentate phosphite ligands, and applied the ligan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574
CPCC07F9/65746
Inventor 张攀科王广柱王丹阳张亚娟赵洪良
Owner ZHENGZHOU UNIV
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