Application of tri-silicon amine rare earth complex to catalyzing of hydroboration reaction of ketone 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 rare earth complexes not found, and achieve the goal of reaction process Simple and controllable, mild reaction conditions, easy synthesis

Active Publication Date: 2016-12-07
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is necessary to explore new catalytic systems to improve the previous deficiencies. So far, no reports have been found about rare earth complexes as catalysts for catalyzing hydroboration reactions.

Method used

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  • Application of tri-silicon amine rare earth complex to catalyzing of hydroboration reaction of ketone and borane
  • Application of tri-silicon amine rare earth complex to catalyzing of hydroboration reaction of ketone and borane
  • Application of tri-silicon amine rare earth complex to catalyzing of hydroboration reaction of ketone and borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment one: La[N(SiMe 3 ) 2 ] 3 Catalytic synthesis of boronate from acetophenone and pinacol borane

[0029] 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, and then add acetophenone (0.117 mL, 1 mmol) with a pipette, After reacting at room temperature for 10 min, use a dropper to draw a drop into the nuclear magnetic tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 98%. NMR data of the product: 1 H NMR (CDCl 3 , 400MHz) δ : 7.28~7.30(m, 2H), 7.21~7.25 (m, 2H), 7.13~7.17 (m, 1H), 5.18 (q, J =6.4 Hz, 1H), 1.42 (d, J = 6.5 Hz, 3H), 1.16+1.13(two s, 6H each).

Embodiment 2

[0030] Embodiment two: Nd[N(SiMe 3 ) 2 ] 3 Catalytic synthesis of boronate from acetophenone and pinacol borane

[0031] Under an inert gas atmosphere, add the catalyst Nd[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, and then add acetophenone (0.117 mL, 1 mmol) with a pipette, After reacting at room temperature for 10 min, use a dropper to draw a drop into the nuclear magnetic tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 93%. The NMR data of the product are the same as in Example 1.

Embodiment 3

[0032] Embodiment three: Sm[N(SiMe 3 ) 2 ] 3 Catalytic synthesis of boronate from acetophenone and pinacol borane

[0033] Under an inert gas atmosphere, the catalyst Sm[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, and then add acetophenone (0.117 mL, 1 mmol) with a pipette, After reacting at room temperature for 10 min, use a dropper to draw a drop into the nuclear magnetic tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 93%. The NMR data of the product are the same as in Example 1.

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Abstract

The invention discloses application of tri-silicon amine rare earth complex to the catalyzing of hydroboration reaction of ketone and borane. The ketone is 2-acetylfuran, 2-acetylthiophene, 2-acetonaphthone or (substituted) phenyl ketone. The application has the advantages that the tri-silicon amine rare earth complex can catalyze the hydroboration reaction of the ketone and the borane under a mild condition (room temperature) in a high activity manner, and the use amount of catalyst is only 0.1-0.5% of the molar weight of the ketone; fast reaction is achieved, yield of above 90% can be reached after the reaction the performed for 10 minutes, catalyst use amount is lowered while yield is increased as compared with an existing catalyzing system, reaction time is short, the reaction condition is mild, and the economic atom synthesizing requirements are well satisfied.

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 ketone and borane. Background technique [0002] Organoboranes are a very important class of intermediates in organic transformations. 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 automobile brake fluids. At the same time, the research as a special surfactant is gradually deepening. Borate ester surfactants with boron-oxygen bonds have good compatibility with macromolecular substances, so they are often used as antistatic agents for synthetic resins. [0003] The easiest way to synthesize boric acid ester is the direct condensation reaction of boric acid and alcohol or phenol. There are also some other methods, such as the direc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04B01J31/22
CPCB01J31/1805B01J2231/344B01J2531/0213B01J2531/37B01J2531/38C07F5/04
Inventor 薛明强武振杰洪玉标沈琪
Owner SUZHOU UNIV
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