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Application of 4-Methoxyanilino Lithium in Catalytic Hydroboration of Imines and Boranes

A methoxyaniline-based, catalytic imine technology, applied in catalytic reactions, chemical instruments and methods, physical/chemical process catalysts, etc., can solve the problems of low yield of catalytic systems, expensive catalysts, long reaction time, etc., to achieve Good universality, short reaction time and high reaction yield

Active Publication Date: 2020-04-17
ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the catalytic systems reported so far, the catalysts are relatively expensive or difficult to prepare, or the reaction time is long and the reaction must be performed at high temperature, and the yield of some catalytic systems is very low

Method used

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  • Application of 4-Methoxyanilino Lithium in Catalytic Hydroboration of Imines and Boranes
  • Application of 4-Methoxyanilino Lithium in Catalytic Hydroboration of Imines and Boranes
  • Application of 4-Methoxyanilino Lithium in Catalytic Hydroboration of Imines and Boranes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment one: 4-methoxyanilinolithium catalyzes the hydroboration reaction of benzidine and pinacol borane

[0025] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylaniline under the protection of argon, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 69.9 ul of 4-formazol Tetrahydrofuran solution (0.3577M) of lithium oxyanilinide (5 mol% dosage, the same below), after reacting for 1 h, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 96%. NMR data of the product: 1 H NMR (CDCl 3 ,400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

Embodiment 2

[0026] Example 2: 4-Methoxyanilino Lithium Catalyzed Hydroboration Reaction of Beniylidene Aniline and Pinacol Borane

[0027] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylaniline under the protection of argon, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 69.9 ul of 4-formazol Lithium oxyanilinide tetrahydrofuran solution (0.3577M) (5 mol% dosage), after 2 hours of reaction, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 99%. NMR data of the product: 1 H NMR (CDCl 3 , 400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

[0028] Substitution of the 4-methoxyanilinidelithium by the amide lithium compound of formula I did not yield the product.

[0029]

Embodiment 3

[0030] Example 3: 4-methoxyanilinolithium catalyzes the hydroboration reaction of benzidine and pinacol borane

[0031] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylaniline under the protection of argon, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 55.9 ul of 4-formazol Lithium oxyanilinide tetrahydrofuran solution (0.3577M) (4 mol% dosage), after reacting for 2 h, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 96%. NMR data of the product: 1 H NMR (CDCl 3 , 400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

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Abstract

The invention relates to an application of 4-methoxyaniline lithium, and concretely relates to an application of 4-methoxyaniline lithium in the catalysis of a hydroboration reaction of imine and borane. A catalyst, borane and imine are stirred and mixed uniformly, the obtained mixture is reacted for 1-2 h, and is exposed to air to terminate the reaction, and the obtained reaction solution undergoes reduced pressure solvent removal to obtain borate with different substituent groups. The 4-methoxyaniline lithium can highly actively catalyze the hydroboration reaction of imine and borane at roomtemperature, the use amount of the catalyst is only 4-5% of the molar quantity of the imine, and the reaction yield can reach 90% or above. Compared with existing catalysis systems, the system in theinvention, using the simple 4-methoxyaniline lithium, has mild reaction conditions, and allows the yield of the borate with different substituent groups under optimized conditions to reach 99%.

Description

technical field [0001] The application of the 4-methoxyanilinolithium involved in the present invention specifically relates to the efficient application of the 4-methoxyanilinolithium in catalyzing the hydroboration reaction of imine and borane. [0002] technical background [0003] Amine compounds and their derivatives are ubiquitous in nature, especially in the biological world, and have extremely important physiological functions. They are important organic compounds in the fields of biology, chemistry, medicine, etc. Many drugs contain amine functional groups, namely amino groups, such as amino groups in proteins, nucleic acids, antibiotics and alkaloids. Amine compounds have many uses and a wide range of applications. They are often used in the synthesis of textiles, dyes, polymers, pigments and pesticides. Since the hydroboration reaction of carbonyl groups is much easier than that of amines, the development of an efficient catalytic system for the hydroboration reac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07F5/04C07F5/02
CPCB01J31/0252B01J2231/643C07F5/022C07F5/04
Inventor 薛明强颜丹丹洪玉标刘倩倩陈素芳沈琪
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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