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Application of n-butyllithium for catalyzing hydroboration of imine and borane

A technology of n-butyllithium and catalytic imine, 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 and reaction time long time, expensive catalysts, etc., to achieve the effects of simple and controllable reaction, short reaction time and mild reaction conditions

Active Publication Date: 2019-02-15
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 n-butyllithium for catalyzing hydroboration of imine and borane
  • Application of n-butyllithium for catalyzing hydroboration of imine and borane
  • Application of n-butyllithium for catalyzing hydroboration of imine and borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: n-Butyl Lithium Catalyzed Hydroboration Reaction of Beniylidene Aniline and Pinacol Borane

[0022] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylaniline under the protection of argon, add 100 ulTHF, then add 0.5 mmol (0.0726 mL) borane with a pipette and mix well, and finally add 25 ul of n-butyl Lithium tetrahydrofuran solution (1M) (5 mol% dosage, the same below), 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 90%. 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: N-butyllithium 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 benzylaniline under argon protection, add 100 ulTHF, then add 0.55 mmol (0.0798 mL) borane with a pipette and mix well, and finally add 25 ul of n-butyl Lithium tetrahydrofuran solution (1M) (5 mol% dosage, the same below), 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 95%. 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 3

[0025] Embodiment three: n-Butyllithium 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 benzylaniline 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 25 ul of n-butyl Lithium tetrahydrofuran solution (1M) (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 , 400 MHz) 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 invention relates to application of n-butyllithium and specifically relates to application of n-butyllithium for catalyzing a hydroboration of imine and borane. In the application, a catalyst, theborane and the imine are sequentially mixed uniformly, a reaction is performed on the mixture for 1-2h, the mixture is exposed to air to terminate the reaction, and the pressure of reaction liquid isreduced to remove a solvent, so as to obtain borate with different substituent groups. The n-butyllithium disclosed by the invention can be used for catalyzing the hydroboration of the imine and theborane in high activity under a room temperature condition, the dosage of the catalyst is 4-5mol% of the molar weight of the imine, and the yield of the reaction can reach above 90%. Compared with theexisting catalytic system, the application utilizes the commercialized reagent n-butyllithium, so that reaction conditions are mild, and the yield of the borate with the different substituent groupsunder limited conditions can reach 99%.

Description

technical field [0001] The application of the commercial reagent n-butyllithium involved in the present invention specifically relates to the application of n-butyllithium to catalyze the synthesis 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 amine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/12C07F5/02
CPCB01J31/122C07F5/022
Inventor 薛明强颜丹丹朱章野武振杰徐晓娟沈琪
Owner SUZHOU UNIV
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