Axial-chirality bidentate ligand and application thereof in copper-catalyzed coupling reaction

A bidentate ligand, coupling reaction technology, applied in catalytic reaction, organic compound/hydride/coordination complex catalyst, preparation of organic compounds, etc., can solve the problems of restricting large-scale application and high synthesis cost, and achieve The effect of mild reaction conditions, simple preparation and high catalyst activity

Inactive Publication Date: 2019-02-15
浙江工业大学上虞研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] After a long period of scientific research and exploration, researchers have gradually solved the limitation that organotin reagents, organozinc reagents, grittin reagents and other organometallic reagents were used in the synthesis of biaryl compounds, reducing the environmental hazards of heavy metals, but There are still some limitations. Generally, the catalyst needs noble metal catalysts such as palladium, and the synthesis cost is relatively high, which restricts the large-scale application of this reaction.

Method used

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  • Axial-chirality bidentate ligand and application thereof in copper-catalyzed coupling reaction
  • Axial-chirality bidentate ligand and application thereof in copper-catalyzed coupling reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Add 50mg of trimethoxyphenyl silicon and 45mg of bromobenzene into a 10mL single-port reaction flask, add 2mL of ethanol to dissolve, then add 35mg of KOH, add 5mol% of CuCl and A 1 After compounding the catalyst, the reaction was raised to 100° C., and the reaction was carried out for 6 hours. After the reaction was completed, it was directly passed through the column to obtain a white solid product with a yield of 56%.

Embodiment 2

[0018] Add 50mg of trimethoxyphenyl silicon and 45mg of bromobenzene into a 10mL single-port reaction flask, add 2mL of ethanol to dissolve, then add 35mg of KOH, add 5mol% of CuCl and A 1 After compounding the catalyst, the reaction was raised to 100° C. for 12 hours. After the reaction was completed, it was directly passed through the column to obtain a white solid product with a yield of 81%.

Embodiment 3

[0020] Add 50mg of trimethoxyphenyl silicon and 45mg of bromobenzene into a 10mL single-port reaction flask, add 2mL of ethanol to dissolve, then add 35mg of KOH, add 5mol% of CuBr and A 1 After compounding the catalyst, the reaction was raised to 100° C. for 12 hours. After the reaction, it was directly passed through the column to obtain a white solid product with a yield of 86%.

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Abstract

The invention discloses an axial-chirality bidentate ligand and application thereof in a copper-catalyzed coupling reaction. The structural formula of the axial-chirality bidentate ligand is shown inthe original specification, wherein R is 2-Me or 3-Ome or 32-t-Bu or 32-F or 32, 3, 4-F. The application of the axial-chirality bidentate ligand in the copper-catalyzed coupling reaction comprises thefollowing steps: stirring the ligand and copper salt in diethyl ether for coordination, concentrating and performing spin drying, so as to obtain a catalyst; adding trimethoxyphenyl-silicon and bromobenzene into a 10mL single aperture reaction flask, adding ethanol into the reaction flask for dissolving, adding alkali into the reaction flask and 5mol% of the catalyst, rising the temperature of the reaction to 60-100 DEG C, performing a reaction for 6-12h and directly performing column chromatography after the reaction is ended, so as to obtain a white solid product. According to the axial-chirality bidentate ligand and the application thereof in the copper-catalyzed coupling reaction, the technical problem that how the relatively high yield is obtained under a mild condition can be solved.

Description

technical field [0001] The invention belongs to the field of metal catalysis, and in particular relates to an axial chiral bidentate ligand and its application in Nozaki-Hiyama-Kishi decarboxylation C-C coupling reaction. Background technique [0002] In recent years, the metal palladium-catalyzed decarboxylation coupling reaction has received more and more attention, and great research progress has been made, especially in the synthesis of diaryl compounds. For example, Germany The BASF company of the BASF company has discovered a new drug with a good inhibitory effect on fungi by using the synthesis technology of diaryl compounds. [0003] Goossen et al. reported that palladium catalyzed the decarboxylation of 2-nitrobenzoic acid and the coupling of bromobenzene to prepare diaryl compounds. This study provided a method for the preparation of biphenyl compounds by decarboxylation. The key synthesis steps of new drug pharmaceutical intermediates, the reaction steps are as f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/056B01J31/22C07C1/32C07C15/14C07C41/30C07C43/205C07C201/12C07C205/06C07D213/16C07D213/127
CPCC07D491/056B01J31/183B01J2231/4205B01J2531/0266B01J2531/16C07C1/321C07C41/30C07C201/12C07D213/127C07D213/16C07C15/14C07C43/205C07C205/06
Inventor 方标许萌柯军梁王哲
Owner 浙江工业大学上虞研究院有限公司
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