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Application of Lithium Anilide in Catalytic Hydroboration of Imine and Borane

A technology of anilinolithium and catalytic imine, which is 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, expensive catalyst, Long reaction time and other problems, to achieve the effect of good universality, short reaction time, high reaction yield

Active Publication Date: 2021-07-09
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 Lithium Anilide in Catalytic Hydroboration of Imine and Borane
  • Application of Lithium Anilide in Catalytic Hydroboration of Imine and Borane
  • Application of Lithium Anilide in Catalytic Hydroboration of Imine and Borane

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Embodiment 1: Lithium anilide 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 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 43.4 ul lithium anilide Tetrahydrofuran solution (0.5759M) (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 , 400MHz) δ: 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

Embodiment 2

[0024] Embodiment 2: Lithium anilide catalyzes the hydroboration reaction of benzidine and pinacol borane

[0025] In the reaction flask that has been dehydrated and deoxygenated, under the protection of argon, add 0.5 mmol of benzylaniline, add 100ul THF, then add 0.55 mmol (0.0798 mL) borane with a pipette and mix well, and finally add 43.4 ul lithium anilide Tetrahydrofuran solution (0.5759M) (5 mol% dosage, the same below), after reacting for 2 h, draw a drop into the NMR tube with a dropper, and add CDCl3 to form a solution. The calculated 1H spectrum yield was 95%. NMR data of the product: 1H NMR (CDCl3, 400MHz) δ: 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

Embodiment 3

[0026] Embodiment 3: Lithium anilide 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 gun and mix well, and finally add 43.4 ul lithium anilide Tetrahydrofuran solution (0.5759M) (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 , 400 MHz) δ :7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

[0028] Replacing the lithium anilide with the lithium amidide compound of formula I did not yield the product.

[0029]

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Abstract

The present invention relates to the application of anilinolithium, in particular to the application of anilinolithium 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 anilinolithium disclosed in the present invention can catalyze the hydroboration reaction of imine and borane with high activity at room temperature, the amount of catalyst is only 4-5 mol% of the molar weight of imine, and the reaction can reach a yield of more than 90%. , compared with the existing catalytic system, the simple anilinolithium is used, the reaction conditions are mild, and the yield of borate esters with different substituents can reach 99% under optimized conditions.

Description

technical field [0001] The application of anilinolithium involved in the present invention specifically relates to the efficient application of anilinolithium 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. In the prior art, there is a hydroboration reaction about the C=O bond. Since the hydroboration reaction of the carbonyl group is far more likely to occur than the hydroboration reaction of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02B01J31/02
CPCB01J31/0252C07F5/027
Inventor 薛明强颜丹丹徐晓娟朱章野武振杰沈琪
Owner SUZHOU UNIV
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