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Application of Trisiliconamine Rare Earth Complex in Catalytic Hydroboration of Aldehyde and Borane

A technology of rare earth complexes and trisilicon amines, applied in catalytic reactions, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc., can solve the problems of long reaction time, low substrate universality, The problem of large amount of catalyst is used to achieve the effect of fast reaction speed, simple and controllable reaction process, and simple structure

Active Publication Date: 2018-05-29
ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, in the existing catalytic system, the amount of catalyst is relatively large, the reaction time is relatively long, and the substrate universality is low.

Method used

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  • Application of Trisiliconamine Rare Earth Complex in Catalytic Hydroboration of Aldehyde and Borane
  • Application of Trisiliconamine Rare Earth Complex in Catalytic Hydroboration of Aldehyde and Borane
  • Application of Trisiliconamine Rare Earth Complex in Catalytic Hydroboration of Aldehyde and Borane

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment one: La[N(SiMe 3 ) 2 ] 3 Catalytic synthesis of boronate from benzaldehyde and pinacol borane

[0026] Under an inert gas atmosphere, the catalyst La[N(SiMe 3 ) 2 ] 3 hexane solution (0.1 mL, 0.01 mol / L), then add pinacol borane (0.145 mL, 1 mmol) with a pipette, then add benzaldehyde (0.101 mL, 1 mmol) with a pipette, and react at room temperature After 10min, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 95%. Dry CDCl under reduced pressure 3 and a mixed solution of hexane, add n-hexane (3 × 2mL), and drain to obtain the corresponding pinacol borate, C 6 h 5 CH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O).

Embodiment 2

[0027] Embodiment two: La[N(SiMe 3 ) 2 ] 3 Catalytic synthesis of boronate from benzaldehyde and pinacol borane

[0028] Under an inert gas atmosphere, the catalyst La[N(SiMe 3 ) 2 ] 3 hexane solution (0.25 mL, 0.01 mol / L), then add pinacol borane (0.145 mL, 1 mmol) with a pipette, then add benzaldehyde (0.101 mL, 1 mmol) with a pipette, room temperature After reacting for 10 min, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 94%. Dry CDCl under reduced pressure 3 and a mixed solution of hexane, add n-hexane (3 × 2mL), and drain to obtain the corresponding pinacol borate, C 6 h 5 CH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O).

Embodiment 3

[0029] Embodiment three: La[N(SiMe 3 ) 2 ] 3 Catalytic synthesis of boronate from benzaldehyde and pinacol borane

[0030] Under an inert gas atmosphere, the catalyst La[N(SiMe 3 ) 2 ] 3 hexane solution (0.5 mL, 0.01 mol / L), then add pinacol borane (0.145 mL, 1 mmol) with a pipette, then add benzaldehyde (0.101 mL, 1 mmol) with a pipette, and react at room temperature After 10 min, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 90%. Dry CDCl under reduced pressure 3 and a mixed solution of hexane, add n-hexane (3 × 2mL), and drain to obtain the corresponding pinacol borate, C 6 h 5 CH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O).

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Abstract

The invention discloses application of a trisilazane-rare earth complex in catalysis of hydroboration reaction between aldehyde and borane. The trisilazane-rare earth complex disclosed by the invention can be used for catalyzing the hydroboration reaction between aldehyde and borane in a high activity manner under a mild condition (room temperature), and the dosage of a catalyst is only 0.1%-0.5% of molar ratio of aldehyde; the reaction speed is very high, the yield higher than 90% can be achieved after 10 minutes of reaction; compared with existing catalytic systems, the application has the advantages that the dosage of the catalyst is reduced, the yield is increased, the required time is short, the reaction condition is mild, and atom economy synthesis is highly met.

Description

technical field [0001] The invention relates to an application technology of a metal organic complex, in particular to the application of a trisiliconamine rare earth complex in catalyzing the hydroboration reaction of aldehyde and borane. Background technique [0002] Borate compounds have a wide range of applications, not only as polymer additives, gasoline additives, sterilizers, flame retardants, but also as lubricating oil additives and automotive brake fluids. In 1939, researchers discovered that under the condition of no catalyst, aldehydes may undergo hydroboration reduction reaction with diborane, which opened up a new way for the synthesis of borate esters with various substituents. Most importantly, the addition reaction of carbonyl compounds and boranes is the most direct and atom-economical method for the synthesis of boronic acid esters with different substituents. However, studies have shown that some boranes (such as pinacol borane) are difficult to undergo ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/04B01J31/22
CPCB01J31/1805B01J2231/344B01J2531/0213B01J2531/37C07F5/04
Inventor 薛明强武振杰洪玉标沈琪
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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