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Synthetic method of alkenyl borate compound

A kind of technology of alkenyl borate and synthesis method, which is applied in the field of organic synthesis and transition metal catalysis, can solve the problems of poor compatibility of functional groups, low atom economy, poor regioselectivity, etc., and achieve mild conditions, high atom economy, The effect of easy operation

Active Publication Date: 2019-11-22
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the traditional synthetic methods that have been reported so far still have disadvantages such as low atom economy, poor functional group compatibility, and poor regioselectivity.
In addition, most of the recent preparation methods need to start from pre-functionalized alkenes or boranes, which are costly

Method used

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  • Synthetic method of alkenyl borate compound
  • Synthetic method of alkenyl borate compound
  • Synthetic method of alkenyl borate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 A kind of synthetic method of alkenyl borate compound:

[0023]

[0024] Add styrene 1a (0.2 mmol, 23 μL), pinacol borane 2a (0.2 mmol, 29 μL), toluene (1 mL), Cp 2 ZrH 2 (0.01 mmol, 2.3 mg), stirred at 25°C for 10 minutes under nitrogen (1 atm) atmosphere. GC detected that the reaction was complete. Diatomaceous earth filtration, the solvent was spin-dried under reduced pressure, and the residue was purified by silica gel column chromatography, using petroleum ether: ethyl acetate (40 mL: 1 mL) as the eluent to obtain a colorless oily substance, styrene boric acid pina Alcohol ester 3a (42 mg, 92%).

[0025] The characterization data of this compound are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.49 (d, J =7.7 Hz, 2H), 7.40 (d, J = 18.4 Hz, 1H), 7.32 (m, 3H), 6.17 (d, J = 18.4 Hz,1H), 1.32 (s, 12H). 13 C NMR (101 MHz, Chloroform- d ) δ 149.5, 137.5, 128.9, 128.6, 127.1, 83.3, 24.8. 11 B NMR (128 MHz, Chloroform- d ) δ 30.38.

Embodiment 2

[0026] Embodiment 2 A kind of synthesis method of alkenyl borate compound:

[0027]

[0028] Add styrene 1a (0.2 mmol, 23 μL), pinacol borane 2a (0.2 mmol, 29 μL), toluene (1 mL), Cp 2 ZrH 2 (0.01 mmol, 2.3 mg), the reaction was stirred at 25°C for 10 minutes under an argon (1 atm) atmosphere. GC detected that the reaction was complete. Diatomaceous earth filtration, the solvent was spin-dried under reduced pressure, and the residue was purified by silica gel column chromatography, using petroleum ether: ethyl acetate (40 mL: 1 mL) as the eluent to obtain a colorless oily substance, styrene boric acid pina Alcohol ester 3a (41 mg, 90%).

[0029] The characterization data of this compound are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.49 (d, J =7.7 Hz, 2H), 7.40 (d, J = 18.4 Hz, 1H), 7.32 (m, 3H), 6.17 (d, J = 18.4 Hz,1H), 1.32 (s, 12H). 13 C NMR (101 MHz, Chloroform- d ) δ 149.5, 137.5, 128.9, 128.6, 127.1, 83.3, 24.8. 11 B NMR (128 MHz, Chloroform- d ...

Embodiment 3

[0030] Embodiment 3 A kind of synthesis method of alkenyl borate compound:

[0031]

[0032] Add styrene 1a (0.2 mmol, 23 μL), pinacol borane 2a (0.2 mmol, 29 μL), toluene (1 mL), Cp 2 ZrH 2 (0.01 mmol, 2.3 mg), stirred and reacted at 0°C for 8 hours under nitrogen (1 atm) atmosphere. Diatomaceous earth filtration, the solvent was spin-dried under reduced pressure, and the residue was purified by silica gel column chromatography, using petroleum ether: ethyl acetate (40 mL: 1 mL) as the eluent to obtain a colorless oily product, styrene boric acid pinacol Ester 3a (8.2 mg, 18%).

[0033] The characterization data of this compound are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.49 (d, J =7.7 Hz, 2H), 7.40 (d, J = 18.4 Hz, 1H), 7.32 (m, 3H), 6.17 (d, J = 18.4 Hz,1H), 1.32 (s, 12H). 13 C NMR (101 MHz, Chloroform- d ) δ 149.5, 137.5, 128.9, 128.6, 127.1, 83.3, 24.8. 11 B NMR (128 MHz, Chloroform- d ) δ 30.38.

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Abstract

The invention relates to a synthesis method of an alkenyl borate compound, which comprises the following steps: dissolving an olefin compound and a borane compound in a solvent, adding a zirconium catalyst, reacting at 0-150 DEG C for 5 minutes to 8 hours in a protective atmosphere, and separating to obtain the alkenyl borate compound. The method is simple and convenient to operate, low in cost, high in reaction atom economy and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis and transition metal catalysis, in particular to a method for synthesizing alkenyl borate compounds. Background technique [0002] Alkenyl boronic esters are important intermediates for the synthesis of carbon-carbon bonds, carbon-halogen bonds, carbon-oxygen bonds, and carbon-nitrogen bonds in synthetic organic chemistry, and are widely found in natural products and have significant biological and potential drugs. Among the active compounds, it has important research significance and application value in the fields of organic chemistry and medicinal chemistry. The carbon-carbon double bond provides multifunctional boron-containing compounds compared to saturated alkyl borates. Recent findings have also revealed potential medicinal and medicinal properties of vinyl borates. [0003] Given their importance, new methods for the synthesis of this class of compounds have now been developed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F17/02
CPCC07F5/025C07F17/02
Inventor 吴立朋师晓楠
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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