Novel method for synthesizing potassium aryl trifluoroborate

A technology of potassium aryl trifluoroborate and potassium trifluoroborate, which is applied in the field of synthesizing potassium aryl trifluoroborate, can solve the problems such as no public data reports and the like, and achieve the effect of direct and efficient synthesis and good stability

Active Publication Date: 2015-09-30
CANGZHOU PURUI DONGFANG SCI & TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is the most direct and effective one-step coupling method for synthesis, but there is still no public information report

Method used

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  • Novel method for synthesizing potassium aryl trifluoroborate
  • Novel method for synthesizing potassium aryl trifluoroborate

Examples

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Effect test

Embodiment 1

[0024] Synthesis of potassium trifluoroborate biborate:

[0025] Under nitrogen protection, tetrakis(tetrahydropyrrole) biboron (0.15 mol) and 18-20 equivalents of absolute ethanol were added into a three-neck flask equipped with dropping and reflux devices, and the temperature was raised to reflux for reaction. After refluxing for about 1-2 hours, start to replace it with an atmospheric distillation device to distill out the tetrahydropyrrole generated during the reaction. At this time, the ethanol solvent will also be taken out at the same time. During the whole distillation process, ethanol needs to be replenished from the dropping funnel . When the solvent to be distilled out no longer contains tetrahydropyrrole, get the reaction liquid gas phase detection to confirm that the reaction is complete, after cooling this time, obtain 25.9 grams of colorless liquid after rectification under reduced pressure, HNMR and GC-MS confirm that it is Tetra(B) Oxygen) biboron. Add 120 m...

Embodiment 2

[0027] Synthesis of potassium trifluoroborate biborate:

[0028] Under nitrogen protection, tetrakis(tetrahydropyrrole) biboron (0.1 mole) and 50-60 times deionized water were added into a three-neck flask equipped with dropping and reflux devices, and the temperature was raised to 100° C. for reflux reaction. After refluxing for 1.5 hours, replace it with an atmospheric distillation device, and distill out the tetrahydropyrrole generated during the reaction. When the tetrahydropyrrole is no longer used for distillation, cool the reaction solution to room temperature. At this time, solids are precipitated. After filtering and drying, Obtain 8.5 grams of white solid tetrahydroxydiboron, the HNMR purity is more than 98%, consistent with the literature. Add 45 ml of methanol, stir at room temperature until completely dissolved (about 10-15 minutes), then add KHF 2 Aqueous solution (0.38 mol) was stirred at room temperature for 1 hour. The system was allowed to stand still and se...

Embodiment 3

[0030] Synthesis of Potassium Phenylboronic Acid Trifluoroborate:

[0031] Under the protection of nitrogen, in a 100 ml three-necked flask, add potassium trifluoroborate (0.022 mol), bromobenzene (0.02 mol), 1M potassium carbonate solution (0.04 mol) and 65 ml of ethanol into a 100 ml three-necked flask, stir well, plug in Air tube to the liquid surface of the solution, nitrogen bubbling deoxygenation about 10-20 minutes. Subsequently, 1.0% mole of the prepared palladium catalyst (phenylethylamine, palladium acetate, potassium tert-butoxide and X-Phos is obtained after the reaction, preparation method reference: J.Am.Chem.Soc., 2010,132, 17701) nitrogen join under protection, 80 o C was reacted overnight. After the detection reaction was completed, diatomaceous earth was filtered. The filtrate was spin-dried under reduced pressure and high vacuum, 50 ml of acetone was added, the insoluble solids were filtered off, the filtrate was spin-dried again (if it could not be s...

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Abstract

The invention discloses a novel method for synthesizing potassium aryl trifluoroborate. The novel method comprises the following steps: enabling backflow reaction of tetra(pyrrolidine) diboron in excessive alcohol or water to obtain tetra(alkoxy) diboron, and adding a potassium bifluoride water solution so as to obtain potassium trifluoroborate diboron acid, wherein a boronizing agent is white crystalline solid, is stable in air and moisture and is suitable for being stored for a long time. The agent and aryl halide are adopted to be subjected to Suzuki coupling so as to obtain the potassium aryl trifluoroborate salt, the operation is simple and convenient, the yield is high, and corrosion to glass equipment and reaction kettles can be avoided.

Description

technical field [0001] The invention relates to a new method for synthesizing potassium aryl trifluoroborate, which belongs to the technical field of boron chemical synthesis. Background technique [0002] Palladium-catalyzed cross-coupling, also known as Suzuki coupling, has been widely used in the fields of pharmaceuticals, electronics, and advanced materials since it was first reported in 1979, and has become an indispensable and effective means for constructing complex molecules. [0003] As an important raw material for the coupling reaction, the synthesis of boric acid and boric acid ester has always been the focus of attention in the chemical community. As a supplement to the method of synthesizing boric acid with Grignard or organolithium reagents and trimethyl borate, for some complex molecular boric acids Compounds have been developed one after another: biboronic acid pinacol ester, biboronic acid neopentyl glycol ester, biboronic acid catechol ester and biboronic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/027
Inventor 冷延国李娟娟郭世学
Owner CANGZHOU PURUI DONGFANG SCI & TECH
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