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Application of p-tolylanilide Lithium in Catalytic Hydroboration of Imine and Borane

A technology based on methylaniline and catalytic imine, which is applied in the direction of chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc. long time, expensive catalyst, etc., to achieve the effect of wide substrate application range, short reaction time and good universality

Active Publication Date: 2020-12-18
NANTONG TEXTILE & SILK IND TECH RES INST +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 p-tolylanilide Lithium in Catalytic Hydroboration of Imine and Borane
  • Application of p-tolylanilide Lithium in Catalytic Hydroboration of Imine and Borane
  • Application of p-tolylanilide Lithium in Catalytic Hydroboration of Imine and Borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Lithium p-methylanilide 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 0.5 mmol (0.0726 mL) borane with a pipette and mix well, and finally add 34.4 ul of p-methyl Tetrahydrofuran solution (0.7273M) of lithium anilide (5 mol% dosage, the same below), after reacting for 2 h, draw a drop into the NMR tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 91%. NMR data of the product: 1 H NMR (CDCl 3 ,400 MHz) δ: 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

Embodiment 2

[0026] Embodiment two: p-methylanilide lithium catalyzes the hydroboration reaction of benzidine 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 34.4 ul of p-methyl Tetrahydrofuran solution (0.7273M) of lithium anilide (0.7273M) (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, 1H), 1.29 (s, 12H).

Embodiment 3

[0028] Example 3: Lithium p-methylanilide catalyzes the hydroboration reaction of benzidine and pinacol borane

[0029] 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 34.4 ul of p-methyl Tetrahydrofuran solution (0.7273M) of lithium anilide (5 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 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).

[0030] Substitution of p-toluidelithium by the amide lithium compound of formula I did not yield the product.

[0031]

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Abstract

The invention relates to an application of p-methylaniline lithium, and concretely relates to an application of p-methylaniline 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 undergoesreduced pressure solvent removal to obtain borate with different substituent groups. The p-methylaniline lithium can highly actively catalyze the hydroboration reaction of imine and borane at room temperature, 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 the invention, using the p-methylaniline 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 p-methylanilide lithium involved in the present invention specifically relates to the efficient application of the p-methylanilide lithium 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): C07F5/02B01J31/02
CPCB01J31/0252C07F5/022
Inventor 薛明强徐晓娟颜丹丹武振杰朱章野沈琪
Owner NANTONG TEXTILE & SILK IND TECH RES INST
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