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Bipyridine ligands with axial chirality and synthesis method thereof

一种联吡啶类、合成方法的技术，应用在具有轴手性的联吡啶配体及其合成领域，能够解决应用鲜有报道、吡啶配体发展少等问题，达到反应步骤少、收率高的效果

Active Publication Date: 2021-09-03
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] From the above examples, we can see that the development of axial chiral bipyridyl ligands that conduct and control chirality through the chiral backbone is less developed, and its application in asymmetric reactions is rarely reported.

Method used

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  • Bipyridine ligands with axial chirality and synthesis method thereof
  • Bipyridine ligands with axial chirality and synthesis method thereof
  • Bipyridine ligands with axial chirality and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the synthesis of bipyridine ligand 4

[0043]

[0044] Add diol 1 (2.080g, 20mmol), pyridine 2 (9.72g, 44mmol), and triphenylphosphine (12.6g, 48mmol) into a 250mL reaction flask under nitrogen protection, and add 80mL tetrahydrofuran at 0°C and stir to dissolve. DIAD (9.70 g, 48 mmol) was dissolved in 20 mL of tetrahydrofuran solution dropwise from the constant pressure dropping funnel. After the dropwise addition, the system was an orange-red transparent solution. After 28 hours of reaction, only a small amount of raw materials remained, and the reaction was stopped.

[0045]First spin dry THF, add 20mL dichloromethane to dissolve, add a large amount of petroleum ether, until a large amount of solids precipitate (mostly the reduction product of triphenoxyphosphine and DIAD. If it cannot be precipitated, scrape the bottle wall repeatedly with a small spoon), pump Filtrate (wash the solid with petroleum ether several times during suction filtration, ch...

Embodiment 2

[0047] Embodiment 2: the synthesis of bipyridine ligand 8

[0048]

[0049] Add pyridine 5 (6.458g, 60mmol) to tetrahydrofuran / water (50 / 50mL) mixed solution, stir to dissolve and then add iodine (16.8g, 66mmol) and sodium bicarbonate (5.281g, 66mmol) to the reaction flask, at room temperature After 3 days of reaction, the reaction solution was purple-black, and solids were precipitated. Add 10% sodium thiosulfate solution until the purple-black color disappeared, and a large amount of white solids precipitated. 8.19 g of off-white solids were obtained by suction filtration, which was verified as product 6 by NMR.

[0050] Add diol (2.080g, 20mmol), pyridine 6 (10.3g, 44mmol), and triphenylphosphine (12.6g, 48mmol) into a 250mL reaction flask under nitrogen protection, and add 80mL tetrahydrofuran at 0°C and stir to dissolve. DIAD (9.70 g, 48 mmol) was dissolved in 20 mL of tetrahydrofuran solution dropwise from the constant pressure dropping funnel. After the dropwise addi...

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Abstract

The invention relates to bipyridine ligands with axial chirality, which are designed and synthesized by the following steps of: taking a compound 3-hydroxy-2-halogenated pyridine as an initial raw material, carrying pyridine on a chiral skeleton by reacting with Mitsunobu of chiral diol, and then realizing coupling of the pyridine by utilizing Ullmann reaction promoted by nickel (0) or copper (0), so as to obtain the bipyridine ligands with axial chirality induced by the chiral diol. The method is easy and convenient to operate, high in yield and more practical compared with a traditional method.

Description

[0001] The patent application of the present invention is a divisional application of the Chinese invention patent application with the filing date of November 28, 2014, the application number of 201410708419.2, and the title of the invention "a class of bipyridyl ligands with axial chirality and its synthesis method". technical field [0002] The invention belongs to the field of organic synthesis, and in particular relates to a class of bipyridine ligands with axial chirality and a synthesis method thereof. Background technique [0003] Chiral bipyridyl ligands have been widely concerned by scientific researchers since they were first synthesized in 1984, and thus have been rapidly developed and applied. Chiral bipyridyl ligands can coordinate with a variety of metals to catalyze a series of asymmetric reactions, and gradually develop into an important class of ligands in asymmetric catalytic reactions, especially in reactions catalyzed by transition metals. Therefore, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/147
Inventor 周永贵高翔吴波
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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