Catalytic synthesis application based on frustrated Lewis acid-base pair

A Lewis acid-base pair, catalytic reaction technology, applied in the field of synthesis of β-amino ketones, can solve the problems of difficult to catalyze organic reactions, difficult to reuse, air-sensitive, etc., and achieves low cost, easy operation, and simple reaction conditions. Effect

Inactive Publication Date: 2015-04-22
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, in organic synthesis reactions other than catalytic hydrogenation, hindered Lewis acid-base pairs are difficult to play a role in catalytic organic reactions
Moreover, most hindered Lewis acids and bases are sensitive to air, difficult to reuse, and the reaction process needs to be carried out under the protection of inert gas.
Therefore, conceptually developing novel, air-stable, recyclable bifunctional Lewis acid-base catalysts based on hindered Lewis acid-base pairs remains a great challenge.

Method used

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  • Catalytic synthesis application based on frustrated Lewis acid-base pair
  • Catalytic synthesis application based on frustrated Lewis acid-base pair
  • Catalytic synthesis application based on frustrated Lewis acid-base pair

Examples

Experimental program
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Effect test

preparation example 1

[0023] Add 0.429 g C into a 50 mL two-necked flask 6 h 5 N(C 6 h 4 CH 2 ) 2 SbCl (1.0 mmol), dissolved in 15mL THF solution, and then under nitrogen protection, will contain 0.195g AgBF 4 (1.0 mmol) tetrahydrofuran solution was transferred into the antimony compound solution, stirred at room temperature in the dark for 4 h, then stopped the reaction, and filtered. Add 1.0 mL of n-hexane to the filtrate and keep it at room temperature for 24 h to obtain colorless crystals, which are the target compound hindered Lewis acid-base pair PhN(CH 2 C 6 h 4 ) 2 SbF, the yield is 95.0%.

preparation example 2

[0025] Add 0.05mmol hindered Lewis acid-base pair PhN(CH 2 C 6 h 4 ) 2 SbF, 2.0 mL of dichloromethane, 1.0 mmol of 1,2-epoxycyclohexane and 1.0 mmol of aniline (Ar=Ph) were placed in a water bath reactor with magnetic stirring, and reacted at 25° C. for 8 hours. TLC followed the reaction until the reaction was complete. The reaction result is: (E)-2-anilinocyclohexanol, the yield is 90%, and the selectivity of (E)-2-anilinocyclohexanol is 100%.

preparation example 3

[0027] Add 0.05mmol hindered Lewis acid-base pair PhN(CH 2 C 6 h 4 ) 2 SbF and 2.0mL dichloromethane, 1.0mmol 1,2-epoxycyclohexane and 1.0mmol o-methylaniline (Ar=o-CH 3 C 6 h 4 ), placed in a water-bath reactor with magnetic stirring, and reacted for 10 hours at 25°C. TLC followed the reaction until the reaction was complete. The reaction result is: (E)-2-[(2-methylphenyl)amino]-cyclohexanol, the yield is 82%, (E)-2-[(2-methylphenyl)amino]-cyclohexanol Selectivity is 100%.

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Abstract

The invention provides a synthetic method for catalyzing beta-amino alcohol, alpha, beta-unsaturated ketone and beta-aminoketone based on a frustrated Lewis acid-base pair. A novel frustrated Lewis acid-base pair I which is stable in air is adopted as a catalyst and has the structural formula of PhN(CH2C6H4)2SbF, wherein Sb atom is bonded with two carbon atoms in a ligand and also forms a coordination bond together with nitrogen atom in the ligand. The method provides an efficient and environmental-friendly way for preparing a beta-amino alcohol compound from an epoxy compound and amine, preparing an alpha, beta-unsaturated ketone compound from aldehyde and ketone and preparing beta-aminoketone from aldehyde, ketone and amine. The frustrated Lewis acid-base pair is good in catalytic performance and can be repeatedly used, both the selectivity and the productivity of target products are close to 100%, the reaction conditions are simple, the operation is easy, the cost is low and the preparation process is environmental friendly.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, in particular to a synthesis method based on hindered Lewis acid-base pair catalysis of β-aminoalcohols, α, β-unsaturated ketones and β-aminoketones. 【Background technique】 [0002] Frustrated Lewis acid-base pair (frustrated Lewis pair, FLP) is a system with Lewis electron donor and acceptor at the same time, due to the existence of its steric hindrance, Lewis acid and base will not self-quench, therefore, the system Lewis acid and base sites are capable of reacting with other molecules. This concept was first proposed by Stephan et al. in 2006, which has attracted extensive attention from domestic and foreign chemical colleagues. In recent years, great progress has been made in the research on hindered Lewis acid-base pairs at home and abroad. In the research, it was found that hindered Lewis acid-base pairs can make imines, enamines, enol ethers, etc. Hydrogen effect. In additio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/04C07C215/44C07C215/28C07C45/74C07C49/683C07C49/697C07C49/753C07C225/18C07C221/00
Inventor 邱仁华雷健尹双凤朱龙志曹鑫
Owner HUNAN UNIV
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