Application of Trimethylolene Rare Earth Complex in Catalytic Hydroboration of Imine and Borane

A technology for catalyzing imines and rare earth locenes, which is applied in the directions of organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, chemical instruments and methods, etc. high rate effect

Active Publication Date: 2020-02-11
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report about the hydroboration reaction of such imines catalyzed by rare earth metal complexes, and the present invention is the first case

Method used

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  • Application of Trimethylolene Rare Earth Complex in Catalytic Hydroboration of Imine and Borane
  • Application of Trimethylolene Rare Earth Complex in Catalytic Hydroboration of Imine and Borane
  • Application of Trimethylolene Rare Earth Complex in Catalytic Hydroboration of Imine and Borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment one: La[CpMe] 3 Catalytic synthesis of boronate from benzylidene aniline and pinacol borane

[0029] Under an inert gas atmosphere, add catalytic La[CpMe] to the reaction flask after dehydration and deoxygenation 3 50 mg, add 0.5 mL of tetrahydrofuran, then take 75 μL (0.02 mmol) with a pipette gun and add to another reaction bottle, then add pinacol borane (174 μL, 1.2 mmol) with a pipette gun, and then add benzylidene aniline (0.1812 g, 1 mmol), after reacting at 60°C for 2 days, pipette 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 (400 MHz, CDCl 3 ) δ 7.33 – 7.17 (m, 10H, ArH), 4.73 (s, 2H, NCH 2 ), 1.33 (s, 12H, CH 3 ).

Embodiment 2

[0030] Embodiment two: Nd[CpMe] 3 Catalytic synthesis of boronate from benzylidene aniline and pinacol borane

[0031] Under an inert gas atmosphere, add catalytic Nd[CpMe] to the reaction flask after dehydration and deoxygenation 3 50 mg, add 0.5 mL of tetrahydrofuran, then pipette 76 μL (0.02 mmol) into another reaction bottle, then add pinacol borane (174 μL, 1.2 mmol) with a pipette, and then add benzylidene Benzene (0.1812 g, 1 mmol), after reacting at 60 °C for 2 days, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 84%. The NMR data of the product are the same as in Example 1.

Embodiment 3

[0032] Embodiment three: Y[CpMe] 3 Catalytic synthesis of boronate from benzylidene aniline and pinacol borane

[0033] Under an inert gas atmosphere, add catalytic Y[CpMe] to the reaction flask after dehydration and deoxygenation 3 50 mg, add 0.5 mL of tetrahydrofuran, then pipette 65 μL (0.02 mmol) into another reaction bottle, then add pinacol borane (174 μL, 1.2 mmol) with a pipette, and then add benzyl Aniline (0.1812 g, 1 mmol), after reacting at 60°C for 3 days, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 82%. The NMR data of the product are the same as in Example 1.

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PUM

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Abstract

The invention relates to application of a metal organic complex, in particular to application of a trimethyl cyclopentadienyl rare earth complex in catalysis of imine and borane hydrogenation reaction. A catalyst, borane and imine are mixed evenly in order and subjected to reaction for 2-3 days, CDCl3 is employed to terminate the reaction, and the reaction solution is subjected to pressure reduction to remove the solvent so as to obtain different substituted boric acid ester. The trimethyl cyclopentadienyl rare earth complex provided by the invention can achieve highly active catalysis of theimine and borane hydrogenation reaction under a 60DEG C condition, the catalyst dosage is only 1-2mol% of the imine mole quantity, and the reaction can reach a yield of 80% or more. Compared with theexisting catalytic systems, the trimethyl cyclopentadienyl rare earth complex catalytic system provided by the invention lowers the catalyst dosage and also increases the yield.

Description

technical field [0001] The invention relates to the application field of a metal-organic complex, in particular to the application of a trimethylocene rare earth complex in catalyzing the hydroboration reaction of imine and borane. Background technique [0002] Organic borates can be regarded as orthoboric acid B(OH) 3 Derivatives in which the hydrogen in is replaced by an organic group. Borate ester compounds have a wide range of applications, and they are a major raw material for the synthesis of boron-containing compounds. In addition, boric acid ester compounds can not only be used as rust inhibitors, preservatives, polymer additives, anti-wear additives, automobile brake fluids, gasoline additives, flame retardants, but also can be used as lubricating oil additives, etc. [0003] Since Stock et al.'s pioneering research on borane in 1912, borane has become an important research field in chemistry, and aminoborane compounds have become a hot research field of organobor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02B01J31/22
CPCB01J31/2295B01J2531/0225B01J2531/36B01J2531/37B01J2531/38C07F5/022
Inventor 薛明强徐晓娟颜丹丹朱章野洪玉标沈琪
Owner SUZHOU UNIV
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