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

A technology based on propylaniline and catalytic imine, which is applied in catalytic reactions, chemical instruments and methods, physical/chemical process catalysts, etc., can solve the problems of low yield of catalytic systems, long reaction time, expensive catalysts, etc., and achieve good results. Universal applicability, short response time, simple and controllable response

Active Publication Date: 2021-07-20
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 2,6-Diisopropylanilinide Lithium in Catalytic Hydroboration of Imine and Borane
  • Application of 2,6-Diisopropylanilinide Lithium in Catalytic Hydroboration of Imine and Borane
  • Application of 2,6-Diisopropylanilinide Lithium in Catalytic Hydroboration of Imine and Borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: 2,6-Diisopropylanilide Lithium catalyzes the hydroboration reaction of benzidine and pinacol borane

[0023] 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 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 40.9 ul of 2,6 - Tetrahydrofuran solution (0.6115M) of diisopropylanilinide lithium (5 mol% dosage, the same below), after reacting for 1 h, draw a drop into the NMR 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 (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

[0024] Example 2: 2,6-diisopropylanilide lithium catalyzed hydroboration reaction of benzidine and pinacol borane

[0025] 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 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 40.9 ul of 2,6 - Tetrahydrofuran solution (0.6115M) of diisopropylanilinide lithium (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).

[0026] Replacing lithium 2,6-diisopropylanilide with the lithium amidide compound of formula I failed to obtain the product.

[0027]

Embodiment 3

[0028] Example 3: 2,6-Diisopropylanilide Lithium Catalyzed Hydroboration Reaction of Bianidine and Pinacol Borane

[0029] 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 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 32.7 ul of 2,6 - Tetrahydrofuran solution (0.6115M) of lithium diisopropylanilinide (4 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 97%. 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 present invention relates to the application of 2,6-diisopropylanilinide lithium, in particular to the application of 2,6-diisopropylanilide lithium in catalyzing the hydroboration reaction of imine and borane. Stir and mix the catalyst, borane and imine in sequence, react for 1 to 2 hours, and expose to the air to terminate the reaction, remove the solvent from the reaction solution under reduced pressure, and obtain boric acid esters with different substituents. The 2,6-diisopropylanilinolithium disclosed by the present invention can catalyze the hydroboration reaction of imine and borane with high activity at room temperature, and the amount of catalyst is only 4~5 mol% of the molar weight of imine. It can reach a yield of more than 90%. Compared with the existing catalytic system, the simple 2,6-diisopropylanilinide lithium is used, and the reaction conditions are mild. Under optimized conditions, the borates of different substituents can The yield can reach 99%.

Description

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

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02B01J31/02
CPCB01J31/0238B01J2231/344C07F5/022
Inventor 薛明强颜丹丹陈素芳朱章野蔡玲霞沈琪
Owner NANTONG TEXTILE & SILK IND TECH RES INST
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