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

A rare earth complex, catalytic imine technology, applied in catalytic reactions, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc. Good yield and other problems, to achieve the effects of easy product post-processing, fast reaction speed, and reduced catalyst dosage

Active Publication Date: 2020-01-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After investigating the literature, it was found that there are still many defects in the existing catalytic system, either the reaction temperature is relatively high, or the amount of catalyst is large, and some reactions even take more than three days, but there is no good yield, and it is difficult to realize industrialization Production

Method used

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

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Effect test

Embodiment 1

[0024] Embodiment one: Yb[N(SiMe 3 ) 2 ] 2 Catalytic synthesis of amino borates from benzylidene aniline and pinacol borane

[0025] Under an inert gas atmosphere, add benzylidene aniline (90.62 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, and then add Yb[N(SiMe 3 ) 2 ] 2 Acetonitrile solution (0.1 mL, 0.01mmol), then add pinacol borane (63.99mg, 0.5mmol) with a pipette gun, react at 40°C for 3h, then add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 88%. NMR data of the product: 1 H NMR (400 MHz, CDCl3) δ 7.33 – 7.17 (m, 10H, ArH), 4.73 (s, 2H, NCH 2 ), 1.33 (s, 12H, CH 3 ).

Embodiment 2

[0026] Embodiment two: Eu[N(SiMe 3 ) 2 ] 2 Catalytic synthesis of amino borates from benzylidene aniline and pinacol borane

[0027] Under an inert gas atmosphere, add benzylidene aniline (90.62 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, and then add Eu[N(SiMe 3 ) 2 ] 2 Acetonitrile solution (0.1 mL, 0.01mmol), then add pinacol borane (63.99mg, 0.5mmol) with a pipette gun, react at 40°C for 3h, then add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 82%. NMR data of the product: 1 H NMR (400 MHz, CDCl3) δ 7.33 – 7.17 (m, 10H, ArH), 4.73 (s, 2H, NCH 2 ), 1.33 (s, 12H, CH 3 ).

Embodiment 3

[0028] Embodiment three: Sm[N(SiMe 3 ) 2 ] 2 Catalytic synthesis of amino borates from benzylidene aniline and pinacol borane

[0029] Under an inert gas atmosphere, add benzylidene aniline (90.62 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, and then add Eu[N(SiMe 3 ) 2 ] 2 Acetonitrile solution (0.1 mL, 0.01mmol), then add pinacol borane (63.99mg, 0.5mmol) with a pipette gun, react at 40°C for 3h, then add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 80%. NMR data of the product: 1 H NMR (400 MHz, CDCl3) δ 7.33 – 7.17 (m, 10H, ArH), 4.73 (s, 2H, NCH 2 ), 1.33 (s, 12H, CH 3 ).

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Abstract

The present invention and the application of disilamine rare earth complex in catalyzing the hydroboration reaction of imine and borane, under the protection of nitrogen, sequentially mix imine, disilamine rare earth complex and borane uniformly, and react to obtain amine group borane. The present invention uses the disilamine rare earth complex to catalyze the synthetic reaction of imine and pinacol borane for the first time, thereby developing a new type of highly efficient catalyst for catalyzing the hydroboration reaction. The synthesis method of the disilamine rare earth complex of the present invention is simple , which not only expands the application of disilamine rare earth complexes, but also enriches the synthesis reaction method of imine and pinacol borane. The amount of catalyst is only 2% of the molar amount of imine; the reaction speed is fast, and the yield of more than 80% can be achieved after 3 hours of reaction. Compared with the existing catalytic system, it not only reduces the amount of catalyst, but also improves the yield. The required time is short, the reaction conditions are mild, and conform to atom-economical synthesis.

Description

technical field [0001] The invention relates to the application field of a metal organic complex, in particular to the application of a disilamine rare earth complex in catalyzing the hydroboration reaction of imine and borane. Background technique [0002] Aminoborane compounds have become a hot research field of organoboron compounds in recent years. As a hydrogen storage material and as a reducing agent in organic reactions, chiral catalytic reagents have been widely studied and applied. 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 for cleaning agents, but also as lubricating oil additives. [0003] The synthesis of aminoboranes is generally achieved through the hydroboration of imines, which is atom-economical but accompanied by the formation of multi-substituted products. In recent years, chemists have developed vario...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02B01J31/22
CPCC07F5/022B01J31/1805B01J2531/38B01J2231/344
Inventor 薛明强武振杰朱章野顾佳丽洪玉标沈琪
Owner SUZHOU UNIV
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