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Application of 2,6-Dimethylanilino Lithium in Catalytic Hydroboration of Imine and Borane

A dimethylaniline-based, catalytic imine technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of low yield of catalytic system, reaction Long time, expensive catalyst and other problems, to achieve the effect of good universality, short reaction time, simple and controllable reaction

Active Publication Date: 2020-04-17
SUZHOU UNIV
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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 2,6-Dimethylanilino Lithium in Catalytic Hydroboration of Imine and Borane
  • Application of 2,6-Dimethylanilino Lithium in Catalytic Hydroboration of Imine and Borane
  • Application of 2,6-Dimethylanilino Lithium in Catalytic Hydroboration of Imine and Borane

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: 2,6-Dimethylanilinide Lithium Catalyzed Hydroboration Reaction of Beniylidene Aniline and Pinacol Borane

[0025] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylidene aniline 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 42.2 ul of 2,6 - Tetrahydrofuran solution (0.5926M) of lithium dimethylanilinide (5 mol% dosage, the same below), after reacting for 2 h, draw a drop into the nuclear magnetic tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 90%. NMR data of the product: 1 H NMR(CDCl3, 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] Example 2: 2,6-Dimethylanilinide 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 benzylidene aniline under argon protection, add 100ul THF, then add 0.55 mmol (0.0798 mL) borane with a pipette and mix well, and finally add 42.2 ul of 2,6 - Tetrahydrofuran solution (0.5926M) of lithium dimethylanilinide (5 mol% dosage, the same below), after reacting for 2 h, draw a drop into the nuclear magnetic tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 96%. NMR data of the product: 1 H NMR(CDCl3, 400 MHz) δ: 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29(s, 12H).

Embodiment 3

[0028] Example 3: 2,6-Dimethylanilinide Lithium Catalyzed Hydroboration Reaction of Beniylidene Aniline 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 42.2 ul of 2,6 - Tetrahydrofuran solution (0.5926M) of lithium dimethylanilinide (5 mol% dosage), after reacting for 2 h, draw a drop into the nuclear magnetic tube with a dropper, 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] Replacing lithium 2,6-dimethylanilinide with the lithium amidide compound of formula I failed to obtain the product.

[0031]

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Abstract

The invention relates to application of 2,6-lithium dimethyl aniline, and particularly relates to the application of the 2,6-lithium dimethyl aniline to catalyzing hydroboration of imine and borane. Acatalyst, the borane and the imine are sequentially evenly mixed, reacted for 1-2 hours, and exposed in the air to terminate the reaction, a reaction liquid is decompressed to remove a solvent, and borate having different substituent groups is obtained. The disclosed 2,6-lithium dimethyl aniline can catalyze the hydroboration of the imine and the borane at high activity under the condition of room temperature, the use level of the catalyst is only 4-5 mol% of the molar weight of the imine, the reaction reaches the yield of more than 90%, compared with the existing catalysis system, the simple2,6-lithium dimethyl aniline is used, the reaction condition is mild, and the yield of the borate having different substituent groups is up to 99% under the optimized condition.

Description

technical field [0001] The application of 2,6-dimethylanilinolithium involved in the present invention specifically relates to the efficient application of 2,6-dimethylanilinolithium 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 reacti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07F5/02
CPCB01J31/0252C07F5/02
Inventor 薛明强徐晓娟颜丹丹蔡玲霞郑煜沈琪
Owner SUZHOU UNIV
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