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Alpha-hydroxy pinacol borate compound preparation method

A technology of alcohol borates and compounds, which is applied in the field of preparation of α-hydroxy pinacol borate compounds, can solve the problems of difficult catalyst synthesis, high synthesis cost, sensitive steric hindrance, etc., and achieve good functional group compatibility and reaction High efficiency and mild reaction conditions

Active Publication Date: 2019-11-12
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

At present, there are few methods for synthesizing such compounds, and copper catalysts based on carbene ligands are usually used, which makes the synthesis cost high, the catalyst synthesis is difficult, and this type of reaction substrate is sensitive to steric hindrance

Method used

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preparation example Construction

[0012] One aspect of the embodiments of the present invention provides a method for preparing an α-hydroxy pinacol borate compound, comprising:

[0013] In a protective atmosphere, react the mixed reaction system comprising alcohol compound, double boron reagent, iron catalyst, ruthenium catalyst, phosphorus ligand, basic substance, hydrogen acceptor and solvent at 60-120°C for 1-10h, Then, a quenching agent is added to quench the reaction, and the α-hydroxy pinacol borate compound is obtained through post-treatment.

[0014] In some embodiments, the alcohol compound has the structure shown in formula (II):

[0015]

[0016] Among them, R 1 , R 2 selected from alkyl groups with 1 to 10 carbon atoms.

[0017] Further, the molar ratio of alcohol compound, double boron reagent, iron catalyst, ruthenium catalyst, phosphorus ligand, basic substance and hydrogen acceptor in the mixed reaction system is 1.0:(1.0~3.0):(0.02~0.5 ):(0.01~0.1):(0.01~0.1):(0.1~2.0):(0.1~2.0).

[0...

Embodiment 1

[0038] In the glove box, add biboronic acid pinacol borate, iron catalyst, ruthenium catalyst, ligand, base, hydrogen acceptor, toluene to the Schleck reaction tube, remove from the glove box, and add alcohol under nitrogen atmosphere The compound was then placed in the reaction tube at 100°C for 6 hours. Then adding a quenching agent to quench the reaction, adding ethyl acetate to the system for extraction, and separating by column chromatography to obtain the product.

Embodiment 2-20

[0040] In the glove box, add biboronic acid pinacol borate, iron catalyst, ruthenium catalyst, ligand, base, hydrogen acceptor, toluene to the Schleck reaction tube, remove from the glove box, and add alcohol under nitrogen atmosphere The compound is then placed in the reaction tube at 100°C for 1-6 hours. Then adding a quenching agent to quench the reaction, adding ethyl acetate to the system for extraction, and separating by column chromatography to obtain the product. Wherein, the molar ratio of alcohol compound, diboron reagent, iron catalyst, ruthenium catalyst, phosphorus ligand, basic substance and hydrogen acceptor is 1.0:1.7:0.1:0.02:0.02:0.4:1.0.

[0041] The structure and the productive rate of the alcohol compound used in the embodiment 1-21 of table 1

[0042]

[0043] The product that above all embodiment 1-20 obtains all passes through 1 H-NMR, 13 C-NMR characterization was confirmed, and all unknown samples were confirmed by high-resolution mass spectrome...

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Abstract

The invention discloses an alpha-hydroxy pinacol borate compound preparation method, which comprises: carrying out a reaction on a second mixing reaction system containing an alcohol-based compound, adiboron reagent, an iron catalyst, a ruthenium catalyst, a phosphorus ligand, an alkaline substance, a hydrogen acceptor and a solvent for 1-10 h at a temperature of 60-120 DEG C in a protective atmosphere, adding a quenching agent, carrying out a quenching reaction, and carrying out post-treatment to obtain the alpha-hydroxy pinacol borate compound. According to the present invention, the preparation method has advantages of mild reaction conditions, simple operation, easily available and economical raw materials, efficient reaction, good compatibility with functional groups, and the like.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of α-hydroxy pinacol borate compound. Background technique [0002] α-Hydroxy pinacol borate is a very special class of boron-containing compounds. From the structural point of view, one carbon is connected with a hydroxyl group and a boron group at the same time, which makes the unusual chemical properties of this type of compound. Reactivity, this type of compound can be monofunctionalized or bifunctionalized. In addition, these compounds have high reactivity and can undergo Suzuki-Miyaura coupling reaction. Therefore, it has great application prospects in pharmaceutical synthesis intermediates and organic optoelectronic materials science. In recent years, it has become a research hotspot of organic chemists. At present, there are few methods for synthesizing such compounds, and copper catalysts based on carbene ligands are usually use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 刘超朱庆何泽瑜
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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