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Application of n-butyllithium in catalysis of hydroboration reaction of aliphatic carboxylic acid and borane

一种脂肪族羧酸、正丁基锂的技术，应用在催化反应、物理/化学过程催化剂、有机化合物/氢化物/配位配合物催化剂等方向，能够解决成本高等问题，达到反应时间短、收率高、反应条件温和的效果

Inactive Publication Date: 2020-07-31
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the existing method needs to use a catalyst that is difficult to synthesize, and the cost is high; on the other hand, the catalytic reaction requires 60 o The reaction temperature of C and the reaction time of 24 hours

Method used

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  • Application of n-butyllithium in catalysis of hydroboration reaction of aliphatic carboxylic acid and borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: N-butyllithium catalyzes the hydroboration reaction of acetic acid and pinacol borane

[0024] Under an inert gas atmosphere, add acetic acid (28.6 μL, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (290 μL, 2 mmol) with a pipette gun, and finally add 10 μL n-butyl Lithium tetrahydrofuran solution (0.1M) (0.2 mol% dosage, the same below), reacted at room temperature for 15 minutes, exposed the reaction solution to air, and removed the solvent to obtain the product boric acid ester, which was obtained by s-trimethoxybenzene (84.08 mg , 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 99%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ3.88 (q, 2H, CH 2 ), 1.25 (s, 36H, CH 3 ), 1.21 (br s, 3H, CH 3 ).

[0025] When pinacol borane (218 μL, 1.5 mmol), the yield was 95%; when pinacol borane (363 μL, 2.5 mmol), the yield was...

Embodiment 2

[0026] Example 2: n-Butyl Lithium Catalyzed Hydroboration Reaction of Valeric Acid and Pinacol Borane

[0027] Under an inert gas atmosphere, add valeric acid (54.38 μL, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (290 μL, 2 mmol) with a pipette gun, and finally add n-butyl The tetrahydrofuran solution of lithium (0.2 mol% dosage) was reacted at room temperature for 15 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, with s-trimethoxybenzene (84.12 mg, 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 92%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.81 (t, 2H,OCH 2 ), 1.52-1.56 (m, 2H,CH 2 ), 1.30-1.52 (m, 4H, CH 2 ), 1.28(s, 36H, CH), 0.86(t, 3H, CH 3 ).

Embodiment 3

[0028] Embodiment 3: n-Butyllithium catalyzes the hydroboration reaction of hexanoic acid and pinacol borane

[0029] Under an inert gas atmosphere, add hexanoic acid (62.52 μL, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (290 μL, 2 mmol) with a pipette gun, and finally add n-butyl The tetrahydrofuran solution of lithium (0.2 mol% dosage) was reacted at room temperature for 15 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, with s-trimethoxybenzene (84.01 mg, 0.5 mmol) as the internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 90%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.76 (t, 2H,OCH 2 ), 1.46-1.52 (m, 2H,CH 2 ), 1.24-1.35 (m, 6H, CH 2 ), 1.19 (s, 48H, CH 3 ), 0.82(t, 3H, CH 3 ).

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Abstract

The invention relates to an application of n-butyllithium in catalysis of a hydroboration reaction of aliphatic carboxylic acid and borane. A catalyst, the borane and the carboxylic acid are uniformlystirred and mixed, and reacted for 10-20 minutes, the reaction is terminated by exposing in air, and a solvent is removed through vacuum distillation of the reaction solution to obtain borate with different substituent groups. The n-butyllithium disclosed by the invention can catalyze the hydroboration reaction of carboxylic acid and borane with high activity at room temperature, and the catalystadopted is 0.2 mol% of the carboxylic acid. Compared with the existing catalytic system, the commercial reagent n-butyllithium has advantages of mild reaction condition is mild and capability of enabling the yield of borate with different substituent groups to reach 99% under the limited condition.

Description

[0001] The present invention is a divisional application of the invention titled method for preparing boric acid ester based on the hydroboration reaction of aliphatic carboxylic acid, the application number is 2018115200916, and the application date is December 12, 2018, which belongs to the product application part. technical field [0002] The application of the commercialized reagent n-butyllithium involved in the present invention, in particular, relates to a method for preparing boric acid ester based on hydroboration reaction of aliphatic carboxylic acid. Background technique [0003] Due to its stability and low toxicity, borate is widely used in various fields, and it is a main raw material for the synthesis of boron-containing compounds. On the one hand, the existing method needs to use a catalyst that is difficult to synthesize, and the cost is high; on the other hand, the catalytic reaction requires 60 o C reaction temperature and 24 hours reaction time. The dif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04B01J31/12
CPCB01J31/122B01J2231/42C07F5/04
Inventor 薛明强颜丹丹徐晓娟康子晗洪玉标沈琪
Owner SUZHOU UNIV
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