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New method for selective dehydrogenation boronation reaction by catalyzing methyl ester through ruthenium

A ruthenium-catalyzed methyl ester and selectivity technology, applied in the field of ruthenium-catalyzed selective dehydroboration of methyl ester derivatives, can solve problems that have not yet been discovered

Active Publication Date: 2018-04-20
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] C(sp 3 )-H dehydroboration reaction has not been reported
At the same time, the selective dehydroboration reaction of alkoxy carbon-hydrogen bonds in organic esters has not been discovered so far.

Method used

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  • New method for selective dehydrogenation boronation reaction by catalyzing methyl ester through ruthenium
  • New method for selective dehydrogenation boronation reaction by catalyzing methyl ester through ruthenium
  • New method for selective dehydrogenation boronation reaction by catalyzing methyl ester through ruthenium

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1, wherein methyl ester substrate is as follows:

[0020] Structural formula of methyl ester substrate:

[0021]

[0022] Add ruthenium complex (3.0 mg, 5.6 μmol), ester substrate (0.56 mmol), B 2 pin 2 (0.14g, 0.56mmol) and 1mL tetrahydrofuran. Then the 5 mL sealed tube was tightened and removed from the glove box and placed in an oil bath at 120° C. for heating and stirring for 12 hours. When the reaction solution was cooled to room temperature, the reaction was quenched with ethyl acetate, and then the low-boiling point organic matter was sucked dry on a rotary evaporator. Finally, methylene bromide in an equimolar amount to the substrate was added as an internal standard to measure the NMR yield of the product. After obtaining the NMR yield, the low-boiling organic matter in the crude product was extracted again, and finally, it was separated and purified by column separation. Colorless transparent oil, the eluent used for passing through the colum...

Embodiment 2

[0023] Embodiment 2, wherein methyl ester substrate is as follows:

[0024] Structural formula of methyl ester substrate:

[0025]

[0026] Add ruthenium complex (3.0 mg, 5.6 μmol), ester substrate (0.56 mmol), B 2 pin 2 (0.14g, 0.56mmol) and 1mL tetrahydrofuran. Then the 5 mL sealed tube was tightened and removed from the glove box and placed in an oil bath at 120° C. for heating and stirring for 12 hours. When the reaction solution was cooled to room temperature, the reaction was quenched with ethyl acetate, and then the low-boiling point organic matter was sucked dry on a rotary evaporator. Finally, methylene bromide in an equimolar amount to the substrate was added as an internal standard to measure the NMR yield of the product. After obtaining the NMR yield, the low-boiling organic matter in the crude product was extracted again, and finally, it was separated and purified by column separation. Colorless transparent oil, the eluent used for passing through the colum...

Embodiment 3

[0027] Embodiment 3, wherein methyl ester substrate is as follows:

[0028] Structural formula of methyl ester substrate:

[0029]

[0030] Add ruthenium complex (3.0 mg, 5.6 μmol), ester substrate (0.56 mmol), B 2 pin 2 (0.14g, 0.56mmol) and 1mL tetrahydrofuran. Then the 5 mL sealed tube was tightened and removed from the glove box and placed in an oil bath at 120° C. for heating and stirring for 12 hours. When the reaction solution was cooled to room temperature, the reaction was quenched with ethyl acetate, and then the low-boiling point organic matter was sucked dry on a rotary evaporator. Finally, methylene bromide in an equimolar amount to the substrate was added as an internal standard to measure the NMR yield of the product. After obtaining the NMR yield, the low-boiling organic matter in the crude product was extracted again, and finally, it was separated and purified by column separation. Colorless transparent oil, the eluent used for passing through the colum...

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Abstract

The invention relates to a new method for a selective dehydrogenation boronation reaction by catalyzing a methyl ester derivative through ruthenium. The method comprises the following steps: by usinga hexa-coordinated metal ruthenium complex, containing a norbornadiene (NBD) ligand, as a catalyst and using the methyl ester derivative and bis(pinacolato)diboron as reaction substrates, in a mild reaction condition, efficiently catalyzing a carbon-hydrogen bond of ortho-position methyl of an oxygen atom in the methyl ester derivative to selectively generate a boronation reaction, so as to obtaina corresponding methyl ester borate product. At present, selective dehydrogenation boronation reaction of the carbon-hydrogen bond of the ortho-position methyl of the oxygen atom in an ester derivative is not reported yet. The new method is used for realizing that the methyl ester derivative is enabled to selectively generate the dehydrogenation boronation reaction of the ortho-position methyl ofthe oxygen atom for the first time, and a brand-new reaction strategy is provided for the preparation of a novel organic synthetic intermediate of organic ester borate.

Description

technical field [0001] The invention relates to a new method for ruthenium-catalyzed selective dehydroboration of methyl ester derivatives. Background technique [0002] Methyl ester derivatives are common organic compounds, and their skeletons are widely found in drug molecules and natural products. Therefore, how to convert methyl ester derivatives into more valuable organic compounds has become a key research topic in the field of organic chemistry. In recent years, the transition metal-catalyzed functionalization of carbon-hydrogen bonds is one of the most challenging and interesting topics in organic chemistry. Among them, the metal-catalyzed carbon-hydrogen bond borylation reaction of organic molecules is one of the most important conversion reactions in the carbon-hydrogen bond functionalization, and its product organoborates are very important organic intermediates to construct new molecular systems. Therefore, if the selective borylation reaction of methyl ester d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 姚武冰黄相韵虞美美
Owner TAIZHOU UNIV
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