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Application of biscyclopentadienyl rare-earth metal complex in catalysis of dehydrogenated coupling of amine broane

A technology for catalyzing amine boranes and rare earth metals, applied in organic compound/hydride/coordination complex catalysts, metallocenes, physical/chemical process catalysts, etc., can solve the problem of difficult to control hydrogen release rate, low atom economy, etc. question

Active Publication Date: 2019-05-03
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, the dehydrocoupling reaction of amine boranes provides a straightforward and clean way to synthesize boron-nitrogen bonds, which previously required multi-step and atom-inefficient synthesis.
[0003] Amine borane can release hydrogen gas and form boron-nitrogen bond-containing compounds under heating conditions, but it often needs to be heated to a higher temperature and it is difficult to control the hydrogen release rate

Method used

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  • Application of biscyclopentadienyl rare-earth metal complex in catalysis of dehydrogenated coupling of amine broane
  • Application of biscyclopentadienyl rare-earth metal complex in catalysis of dehydrogenated coupling of amine broane
  • Application of biscyclopentadienyl rare-earth metal complex in catalysis of dehydrogenated coupling of amine broane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] This example provides a method for preparing a dehydrogenated coupling product of amine borane, and its reaction route and specific steps are as follows (wherein, Me represents a methyl group, Cat represents a catalyst, and RT represents room temperature (about 20-30°C) , C 6 D. 6 represents deuterated benzene):

[0060]

[0061] Weigh Cp in the glove box * 2 ScCH(SiMe 3 ) 2 (Cp * =C 5 Me 5 ) 1.4 mg was dissolved in 100 μL deuterated benzene. Weigh 35.3mg dimethylaminoborane (NMe 2 H.BH 3 ), add 400 μL of toluene to dissolve, and quickly add it to the above solution. A large number of hydrogen bubbles were observed immediately, and no obvious bubbles were produced after 2 minutes, and about 0.2 μL was quickly taken out and added to an NMR tube, and 0.5 mL of undried deuterated benzene was added to it to quench the reaction. They were then frozen in liquid nitrogen and thawed until NMR analysis. Subsequently, the raw material conversion rate and product d...

Embodiment 2

[0068] This embodiment provides a method for preparing a dehydrogenated coupling product of amine borane, the reaction scheme is the same as in Example 1, and the specific steps are as follows:

[0069] Weigh Cp in the glove box * 2 ScCH(SiMe 3 ) 2 (Cp * =C 5 Me 5 ) 1.4 mg was dissolved in 100 μL deuterated benzene. Weigh 88.3mg dimethylaminoborane (NMe 2 H.BH 3 ), add 400 μL of toluene to dissolve, and quickly add it to the above solution. A large number of hydrogen bubbles were observed immediately, and no obvious bubbles were produced after 4 minutes, and about 0.2 μL was quickly taken out and added to an NMR tube, and 0.5 mL of undried deuterated benzene was added to it to quench the reaction. They were then frozen in liquid nitrogen and thawed until NMR analysis. Then, the raw material conversion rate and product distribution were analyzed by nuclear magnetic boron spectroscopy, and the raw material conversion rate was measured to be 97.4%, and the calculated TO...

Embodiment 3

[0073] This embodiment provides a method for preparing a dehydrogenated coupling product of amine borane, the reaction scheme is the same as in Example 1, and the specific steps are as follows:

[0074] Weigh Cp in the glove box * 2 LuCH (SiMe 3 ) 2 (Cp * =C 5 Me 5 ) 1.8 mg was dissolved in 100 μL deuterated benzene. Weigh 35.3mg dimethylaminoborane (NMe 2 H.BH 3 ), add 400 μL of toluene to dissolve, and quickly add it to the above solution. Immediately observe the generation of a large number of hydrogen bubbles, wait until 6 minutes when no obvious bubbles are generated, quickly take out about 0.2 μL from it and add it to the NMR tube, and add 0.5 mL of undried deuterated benzene to it to quench the reaction. They were then frozen in liquid nitrogen and thawed until NMR analysis. Subsequently, the raw material conversion rate and product distribution were analyzed by nuclear magnetic boron spectroscopy, and the measured raw material conversion rate was 100%, and th...

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Abstract

The invention relates to an application of a biscyclopentadienyl rare-earth metal complex in catalysis of an intermolecular dehydrogenated coupling reaction of amine broane compounds or amines and borane. A reaction temperature is 10 DEG C to 50 DEG C; and the biscyclopentadienyl rare-earth metal complex has a structural formula shown in the description, wherein RE is Sc, Yt, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb or Lu; R1 is H, C1-C12 alkyl or [tri(C1-C10 alkyl)]silicon group substituted C1-C12 alkyl; and R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11 are independently selectedfrom H, C1-C4 alkyl and cycloalkyl containing 3 to 6 carbon atoms.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to the application of a biscene-based rare earth metal complex in catalyzing the dehydrogenation coupling of amine borane. Background technique [0002] Amine borane compounds have received extensive attention as hydrogen storage materials in recent years, mainly because they have the following advantages: 1. It has a high hydrogen content, and the simplest amine borane (NH 3 .BH 3 ) as an example, its hydrogen content is as high as 19.5wt%. 2. Its properties are relatively stable, and generally exist in a solid state, which is convenient for transportation and can reduce the risk of explosion. On the other hand, the dehydrocoupling reaction of amine boranes provides a straightforward and clean way to synthesize boron-nitrogen bonds, which previously required multi-step and atom-inefficient synthesis. [0003] Amine borane can release hydrogen and form boron-nitrogen bond-contain...

Claims

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Application Information

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IPC IPC(8): C07F17/00B01J31/22C07F5/02C07F5/04
Inventor 徐信许鹏飞
Owner SUZHOU UNIV
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