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Applications of anilino lithium in catalytic hydroboration reaction of imine and borane

A technology of lithium anilide 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 and long reaction time of the catalytic system , the catalyst is expensive and other problems, to achieve the effect of good universality, short reaction time, simple and controllable reaction

Active Publication Date: 2019-01-11
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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  • Applications of anilino lithium in catalytic hydroboration reaction of imine and borane
  • Applications of anilino lithium in catalytic hydroboration reaction of imine and borane
  • Applications of anilino lithium in catalytic hydroboration reaction of imine and borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: Lithium anilide catalyzes the hydroboration reaction of benzidine and pinacol borane

[0022] In the reaction flask that has been dehydrated and deoxygenated, under the protection of argon, add 0.5 mmol of benzylaniline, add 100 ulTHF, then add 0.5 mmol (0.0726 mL) borane with a pipette and mix well, and finally add 43.4 ul of 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 , 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

[0023] Embodiment 2: Lithium anilide catalyzes the hydroboration reaction of benzidine and pinacol borane

[0024] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benidine aniline under the protection of argon, add 100 ulTHF, 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, 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

[0025] Embodiment 3: Lithium anilide catalyzes the hydroboration reaction of benzidine and pinacol borane

[0026] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzidine aniline under the protection of argon, add 100 ulTHF, then add 0.6 mmol (0.0871 mL) borane with a pipette 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).

[0027] Replacing the lithium anilide with the lithium amidide compound of formula I did not yield the product.

[0028]

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Abstract

The invention relates to applications of anilino lithium, and more specifically relates to applications of anilino lithium in catalytic hydroboration reaction of imine and borane. According to a method, a catalyst, borane, and imine are stirred to be uniform, are reacted for 1 to 2h, and are exposed in the air to stop reaction, an obtained reaction solution is subjected to pressure reduction treatment to remove the solvent so as to obtain boric acid esters with different substituent groups. According to the method, anilino lithium is capable of catalyzing hydroboration reaction of imine and borane at room temperature with high activity, the catalyst using amount is only 4 to 5 mol% of the molar amount of imine, reaction yield is as high as 90% or higher. Compared with conventional catalytic systems, the advantages are that: simple anilino lithium is used, reaction conditions are mile, and the yield of boric acid esters with different substituent groups at optimized conditions is capable of reaching 99%.

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. technical background [0002] 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 the ami...

Claims

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Application Information

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Patent Type & Authority Applications(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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